Name: 17407-56-6|(R)-2-Hydroxy-3-methylbutanoic acid|97%
Brand: Ambeed
SKU: A291232
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1
<i>N</i>-methyl-<i>N</i>-(D-α-hydroxy-isovaleryl)-L-isoleucine [ No CAS ]
[ 17407-56-6 ]
[ 4125-98-8 ]

Reference： [1]Experientia,1947,vol. 3,p. 325
Helvetica Chimica Acta,1948,vol. 31,p. 2192,2196,2202

2
[ 640-68-6 ]
[ 17407-56-6 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sulfuric acid; water monomer; NaNO₂ at 60℃; Flow reactor;
80%	With sulfuric acid; NaNO₂ In water monomer at 60℃; Inert atmosphere;
65%	With sulfuric acid; NaNO₂ In water monomer at 0 - 20℃; for 12h;

60%	With sulfuric acid; NaNO₂ In water monomer at 0 - 5℃; for 2h;	1.1.A PREPARATION 1 Synthesis of (2R)-2-hydroxy-3-methyl-butanoic acid Scheme 1, Step A. To a solution of water (45 mL) and sulfuric scid (4 mL; 75 mmol) at 0° C. is added D-valine (10 g; 85.4 mmol). To this solution is slowly added a solution of sodium nitrite (8.8 g; 128 mmol) in water (45 mL) over 2 h, keeping the temperature below 5° C. The mixture is allowed to warm slowly to room temperature. After 2 h, the mixture is extracted with diethyl ether (2*75 mL). The combined ether layers are washed with brine, dried (MgSO4), filtered, and concentrated to provide the title compound as a colorless oil (6.1 g, 60%). This material is used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6): δ 12.38 (broad, 1H), 5.02 (broad, 1H), 3.70 (d, J=4.4 Hz, 1H), 1.92-1.85 (m, 1H), 0.86 (d, J=6.9 Hz, 3H), 0.78 (d, J=6.8 Hz, 3H).
47%	With sulfuric acid; NaNO₂ In water monomer 1.) 0 deg C, 3 h, 2.) RT, 2 h;
40%	With NaNO₂ In sulfuric acid at 0℃; for 2h;
	With hydrogenchloride; silver(I) nitrite
	With hydrogenchloride; glacial acetic acid; NaNO₂
	With sulfuric acid; NaNO₂
	With sulfuric acid; NaNO₂ In water monomer 1.) 0 deg C, 2.) 0 deg C to room temperature, 12 h; Yield given;
	With sulfuric acid; NaNO₂ at 20℃;
	Stage #1: D-Val-OH With glacial acetic acid; NaNO₂ In water monomer Stage #2: With potassium carbonate In methanol; water monomer
	With sulfuric acid; NaNO₂
	With sulfuric acid; NaNO₂ In water monomer at 20℃; for 27h; Cooling with ice;	1. 4.1 D-α-hydroxy acid 10(A-C, G) General procedure: A 60 ml of aqueous solution of sodium nitrite (20.7 g, 0.3 mol) was added into a stirred and ice-cooled solution of D-amino acids (9A-C, G, 50 mmol) in 1 M H2SO4 (100 ml, 0.1 mol) over 3 h, and the mixture was stirred for 24 h at room temperature until the completion of the reaction (monitored by ninhydrin). The mixture was adjusted to pH 6 with solid NaHCO3 and then to pH 3 with concentrated HCl followed by freeze-drying. The resulting residue was extracted with hot acetone (4×100 ml), and the extracts were concentrated and dried to offer colorless oil, to which ether (200 ml) was added and filtrated to remove insoluble solids, the filtrate was concentrated and re-crystallized in ether/hexanes mixture to afford 10(A-C, G) as white crystalline, yield 82%-92%.
	With sulfuric acid; water monomer; NaNO₂ at 20℃; for 10h; Cooling with ice;
	With water monomer; glacial acetic acid; NaNO₂ at 0 - 20℃; for 24h; Inert atmosphere;
230 g	With sulfuric acid; NaNO₂ at 0 - 20℃;	8-1 8-1) Synthesis of A-22-Int2 A-22-Intl (400 g, 3.42 mol) was placed into a 10-L, threenecked flask, and 0.5M H2SO4 (5.2 L) was added. The reaction was cooled to 0°C and then 2 mol/L NaNOz (2.6 L) was added drop wise, after the addition was completed; the reaction was stirred at room temperature overnight. After this time, the reaction mixture was extracted with ethyl acetate (EA) (3 x 3 L) . The combined EA extracts were dried over NazSCM, filtered and concentrated. The resulting crude solid was recrystallized from petroleum ether to afford compound A-22-Int2 (230 g) .1H NMR (400 MHz, CDCI3) data of A-22-Int2 is shown in Fig. 10.
230 g	With sulfuric acid; NaNO₂ at 0 - 20℃;	8-1 8-1) Synthesis of A-22-Int2 A-22-Intl (400 g, 3.42 mol) was placed into a 10-L, threenecked flask, and 0.5M H2SO4 (5.2 L) was added. The reaction was cooled to 0°C and then 2 mol/L NaNOz (2.6 L) was added drop wise, after the addition was completed; the reaction was stirred at room temperature overnight. After this time, the reaction mixture was extracted with ethyl acetate (EA) (3 x 3 L) . The combined EA extracts were dried over NazSCM, filtered and concentrated. The resulting crude solid was recrystallized from petroleum ether to afford compound A-22-Int2 (230 g) .1H NMR (400 MHz, CDCI3) data of A-22-Int2 is shown in Fig. 10.

Reference： [1]Hu, Dennis X.; O'Brien, Matthew; Ley, Steven V. [Organic Letters, 2012, vol. 14, # 16, p. 4246 - 4249]
[2]Lücke, Daniel; Dalton, Toryn; Ley, Steven V.; Wilson, Zoe E. [Chemistry - A European Journal, 2016, vol. 22, # 12, p. 4206 - 4217]
[3]Stein, Jan; Stahn, Sonja; Neudörfl, Jörg-M.; Sperlich, Julia; Schmalz, Hans-Günther; Teusch, Nicole [ChemMedChem, 2018, vol. 13, # 2, p. 147 - 154]
[4]Current Patent Assignee: ELI LILLY & CO - US2014/235718, 2014, A1 Location in patent: Paragraph 0025-0028
[5]Johnson, Rodney L. [Journal of Medicinal Chemistry, 1980, vol. 23, # 6, p. 666 - 669]
[6]Koch, Patrick; Nakatani, Yoichi; Luu, Bang; Ourisson, Guy [Bulletin de la Societe Chimique de France, 1983, vol. 2, # 7/8, p. 185 - 194]
[7]Baker; Meister [Journal of the American Chemical Society, 1951, vol. 73, p. 1336]
[8]Winitz et al. [Journal of the American Chemical Society, 1956, vol. 78, p. 2423,2428]
[9]Gisin,B.F. et al. [Journal of the American Chemical Society, 1969, vol. 91, p. 2691 - 2695]
[10]Kogan, Timothy P.; Somers, Todd C.; Venuti, Michael C. [Tetrahedron, 1990, vol. 46, # 19, p. 6623 - 6632]
[11]James, David G.; Moore, Christopher J.; Aldrich, Jeffrey R. [Journal of Chemical Ecology, 1994, vol. 20, # 12, p. 3281 - 3296]
[12]Uesusuki, Shinya; Watanabe, Bunta; Yamamoto, Shuji; Otsuki, Junko; Nakagawa, Yoshiaki; Miyagawa, Hisashi [Bioscience, Biotechnology and Biochemistry, 2004, vol. 68, # 5, p. 1097 - 1105]
[13]Hanessian; Ma; Wang [Journal of the American Chemical Society, 2001, vol. 123, # 42, p. 10200 - 10206]
[14]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - WO2006/24501, 2006, A1 Location in patent: Page/Page column 13
[15]Jia, Chao; Yang, Ke-Wu; Liu, Cheng-Cheng; Feng, Lei; Xiao, Jian-Min; Zhou, Li-Sheng; Zhang, Yi-Lin [Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 482 - 484]
[16]Location in patent: experimental part Molinski, Tadeusz F.; Reynolds, Kirk A.; Morinaka, Brandon I. [Journal of Natural Products, 2012, vol. 75, # 3, p. 425 - 431]
[17]Kang, Chang Won; Ranatunga, Sujeewa; Sarnowski, Matthew P.; Del Valle, Juan R. [Organic Letters, 2014, vol. 16, # 20, p. 5434 - 5437]
[18]Current Patent Assignee: PRISM BIOLAB - WO2022/75486, 2022, A1 Location in patent: Page/Page column 83; 84
[19]Current Patent Assignee: PRISM BIOLAB - WO2022/75486, 2022, A1 Location in patent: Page/Page column 83; 84

3
[ 4026-18-0 ]
[ 17407-56-6 ]

Reference： [1]Nippon Kagaku Zasshi,1956,vol. 77,p. 284,285
Chem.Abstr.,1958,p. 253
[2]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1962,p. 286 - 288
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1962,p. 310 - 312

4
[ 2503-13-1 ]
[ 17407-56-6 ]
[ 4125-98-8 ]

Reference： [1]Experientia,1947,vol. 3,p. 325
Helvetica Chimica Acta,1948,vol. 31,p. 2192,2196,2202

5
[ 17407-56-6 ]
[ 75-03-6 ]
[ 129025-85-0 ]

Yield	Reaction Conditions	Operation in experiment
72%	With potassium carbonate In acetone for 4h; Reflux;	22.4 Step 4: Preparation of (R)-ethyl 2-hydroxy-3-methylbutanoate; (R)-2-hydroxy-3-methyl-butyric acid (1 g, 8.4 mmol) is dissolved in acetone (50 ml). Thereto, K2CO3 (1.4 g, 10 mmol) and ethyl iodide (2.67 g, excess) are added, and the resulting mixture is refluxed for 4 hours. Then, the mixture is extracted with diethyl ether. The entire extracts are dried over anhydrous MgSO4 and concentrated. The residue is purified by silica gel column chromatography to obtain the compound, (R)-ethyl 2-hydroxy-3-methylbutanoate (0.88 g, 72%).
	With triethylamine In ethyl acetate

Reference： [1]Current Patent Assignee: KAINOS MEDICINE INC; KT&G CORPORATION; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY - US2010/48570, 2010, A1 Location in patent: Page/Page column 64
[2]Luebke,K.; Schroeder,E. [Justus Liebigs Annalen der Chemie, 1963, vol. 665, p. 205 - 212]

6
[ 17407-56-6 ]
[ 100-51-6 ]
benzyl (R)-2-hydroxy-3-methylbutanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: benzyl alcohol With toluene-4-sulfonic acid In benzene for 0.5h; Reflux; Stage #2: (R)-2-Hydroxy-3-methylbutyric acid In benzene Reflux;	1.5 General procedure for the preparation of the D-a-hydroxy acid derivatives 11 (A-G) General procedure: Benzyl alcohol (1.2 equiv) and p-toluenesulfonic acid (0.1 equiv) were taken in benzene and refluxed for 0.5 h, then compounds 10(A-G) (1 equiv) was added, and continuously reflexed until the completion of the reaction (monitored by TLC: petroleum ether/ethyl acetate, 8:1; typically 4 h). The reaction mixture was washed with saturated NaHCO3 solution, water and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. Purification by flash column chromatography gave the desired compounds 11(A-G) as colorless oil.
86%	With thionyl chloride In benzene at 20 - 100℃; Inert atmosphere;
78%	With thionyl chloride In benzene for 40h; Heating;

With hydrogenchloride

Reference： [1]Jia, Chao; Yang, Ke-Wu; Liu, Cheng-Cheng; Feng, Lei; Xiao, Jian-Min; Zhou, Li-Sheng; Zhang, Yi-Lin [Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 482 - 484]
[2]Stein, Jan; Stahn, Sonja; Neudörfl, Jörg-M.; Sperlich, Julia; Schmalz, Hans-Günther; Teusch, Nicole [ChemMedChem, 2018, vol. 13, # 2, p. 147 - 154]
[3]Kogan, Timothy P.; Somers, Todd C.; Venuti, Michael C. [Tetrahedron, 1990, vol. 46, # 19, p. 6623 - 6632]
[4]Gisin,B.F. et al. [Journal of the American Chemical Society, 1969, vol. 91, p. 2691 - 2695] Losse,G.; Klengel,H. [Tetrahedron, 1971, vol. 27, p. 1423 - 1434] Shemyakin,M.M. et al. [Doklady Chemistry, 1961, vol. 140, p. 918 - 921][Doklady Akademii Nauk SSSR, 1961, vol. 140, p. 387 - 390]

7
[ 17407-56-6 ]
[ 73604-37-2 ]
D-α-Hydroxyisovaleryl-Leu-Val-Phe-OCH3 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 24h;

Reference： [1]Johnson, Rodney L. [Journal of Medicinal Chemistry, 1980, vol. 23, # 6, p. 666 - 669]

8
[ 759-05-7 ]
[ 17407-56-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen In water at 35℃; biosynthesis by Proteus vulgaris (potassium phosphate buffer pH 7.0);
	With benzylviologen cation radical In water at 25℃; cell free extract of Proteus vulgaris (potassium phosphate buffer pH 7.0), V_max;

Reference： [1]Schummer, Anita; Yu, Hongtao; Simon, Helmut [Tetrahedron, 1991, vol. 47, # 43, p. 9019 - 9034]
[2]Schummer, Anita; Yu, Hongtao; Simon, Helmut [Tetrahedron, 1991, vol. 47, # 43, p. 9019 - 9034]

9
[ 3715-29-5 ]
[ 17407-56-6 ]

Reference： [1]Agricultural and Biological Chemistry,1986,vol. 50,p. 2621 - 2632

10
[ 17407-56-6 ]
[ 90244-32-9 ]

Yield	Reaction Conditions	Operation in experiment
76%	With sulfuric acid In methanol for 3h; Heating;

Reference： [1]Koch, Patrick; Nakatani, Yoichi; Luu, Bang; Ourisson, Guy [Bulletin de la Societe Chimique de France, 1983, vol. 2, # 7/8, p. 185 - 194]

11
[(1S,2R)-2-((R)-1-Cyano-2-methyl-propoxy)-1-methyl-2-phenyl-ethyl]-trimethyl-ammonium; iodide [ No CAS ]
[ 17407-56-6 ]

Yield	Reaction Conditions	Operation in experiment
61%	With hydrogenchloride at 60℃; for 6h;

Reference： [1]Andres, Celia; Delgado, Manuel; Pedrosa, Rafael; Rodriquez, Raquel [Tetrahedron Letters, 1993, vol. 34, # 51, p. 8325 - 8328]

12
(R)-2-Hydroxy-3-methyl-butyric acid (S)-4,4-dimethyl-2-oxo-1-phenyl-pyrrolidin-3-yl ester [ No CAS ]
[ 17407-56-6 ]

Yield	Reaction Conditions	Operation in experiment
94%	With hydrogenchloride In acetic acid at 120℃;

Reference： [1]Camps, Pelayo; Perez, Francesc; Soldevilla, Nuria [Tetrahedron Asymmetry, 1997, vol. 8, # 11, p. 1877 - 1894]

13
[ 908094-01-9 ]
[ 17407-56-6 ]
[ 90244-32-9 ]

Yield	Reaction Conditions	Operation in experiment
75%
	at 20℃; for 0.5h;
	In methanol; diethyl ether at 20℃; for 0.0833333h;

In diethyl ether at 20℃; for 0.0833333h;

Reference： [1]Pansare, Sunil V.; Ravi, R. Gnana [Tetrahedron, 1998, vol. 54, # 48, p. 14549 - 14564]
[2]Hanessian; Ma; Wang [Journal of the American Chemical Society, 2001, vol. 123, # 42, p. 10200 - 10206]
[3]Choi, Hyukjae; Mevers, Emily; Byrum, Tara; Valeriote, Frederick A.; Gerwick, William H. [European Journal of Organic Chemistry, 2012, # 27, p. 5141 - 5150]
[4]Tan, Karen Co; Wakimoto, Toshiyuki; Abe, Ikuro [Organic Letters, 2014, vol. 16, # 12, p. 3256 - 3259]
[5]Mevers, Emily; Haeckl, F. P. Jake; Boudreau, Paul D.; Byrum, Tara; Dorrestein, Pieter C.; Valeriote, Frederick A.; Gerwick, William H. [Journal of Natural Products, 2014, vol. 77, # 4, p. 969 - 975]

14
[ 219598-65-9 ]
[ 17407-56-6 ]

Yield	Reaction Conditions	Operation in experiment
58%	With sulfuric acid In water at 90℃; for 0.5h;

Reference： [1]Pansare, Sunil V.; Ravi, R. Gnana [Tetrahedron, 1998, vol. 54, # 48, p. 14549 - 14564]

15
[ 928-96-1 ]
[ 17407-56-6 ]
(Z)-3-Hexenyl (R)-2-hydroxy-3-methylbutyrate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With toluene-4-sulfonic acid In benzene for 3h; Heating;

Reference： [1]James, David G.; Moore, Christopher J.; Aldrich, Jeffrey R. [Journal of Chemical Ecology, 1994, vol. 20, # 12, p. 3281 - 3296]

16
[ 10326-41-7 ]
[ 17407-56-6 ]
[ 73-32-5 ]
S-Adenosyl-L-methionine [ No CAS ]
cyclo(N-methyl-L-isoleucyl-D-2-hydroxyisovaleryl-N-methyl-L-isoleucyl-D-lactyl-N-methyl-L-isoleucyl-D-lactyl) [ No CAS ]
(3S,6R,9S,12R,15S,18R)-3,9,15-Tris-((S)-sec-butyl)-6,12-diisopropyl-4,10,16,18-tetramethyl-1,7,13-trioxa-4,10,16-triaza-cyclooctadecane-2,5,8,11,14,17-hexaone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With enniatin synthetase from Fusarium sambucinum BBA 63933; ATP; magnesium chloride In water; glycerol at 27℃; for 0.5h;

Reference： [1]Krause; Lindemann; Glinski; Hornbogen; Bonse; Jeschke; Thielking; Gau; Kleinkauf; Zocher [Journal of Antibiotics, 2001, vol. 54, # 10, p. 797 - 804]

17
[ 72-18-4 ]
[ 17407-56-6 ]
[ 72-19-5 ]
S-Adenosyl-L-methionine [ No CAS ]
(3S,6R,9S,12R,15S,18R)-3-((R)-1-Hydroxy-ethyl)-6,9,12,15,18-pentaisopropyl-4,10,16-trimethyl-1,7,13-trioxa-4,10,16-triaza-cyclooctadecane-2,5,8,11,14,17-hexaone [ No CAS ]
(3S,6R,9S,12R,15S,18R)-3,9-Bis-((R)-1-hydroxy-ethyl)-6,12,15,18-tetraisopropyl-4,10,16-trimethyl-1,7,13-trioxa-4,10,16-triaza-cyclooctadecane-2,5,8,11,14,17-hexaone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With enniatin synthetase from Fusarium scirpi ETH 1536; ATP; magnesium chloride In water; glycerol at 27℃; for 0.5h;

Reference： [1]Krause; Lindemann; Glinski; Hornbogen; Bonse; Jeschke; Thielking; Gau; Kleinkauf; Zocher [Journal of Antibiotics, 2001, vol. 54, # 10, p. 797 - 804]

18
[ 17407-56-6 ]
[ 56-45-1 ]
[ 73-32-5 ]
S-Adenosyl-L-methionine [ No CAS ]
(3S,6R,9S,12R,15S,18R)-3-((S)-sec-Butyl)-9,15-bis-hydroxymethyl-6,12,18-triisopropyl-4,10,16-trimethyl-1,7,13-trioxa-4,10,16-triaza-cyclooctadecane-2,5,8,11,14,17-hexaone [ No CAS ]
(3S,6R,9S,12R,15S,18R)-3,9-Bis-((S)-sec-butyl)-15-hydroxymethyl-6,12,18-triisopropyl-4,10,16-trimethyl-1,7,13-trioxa-4,10,16-triaza-cyclooctadecane-2,5,8,11,14,17-hexaone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With enniatin synthetase from Fusarium sambucinum BBA 63933; ATP; magnesium chloride In water; glycerol at 27℃; for 0.5h;

Reference： [1]Krause; Lindemann; Glinski; Hornbogen; Bonse; Jeschke; Thielking; Gau; Kleinkauf; Zocher [Journal of Antibiotics, 2001, vol. 54, # 10, p. 797 - 804]

19
[ 17407-56-6 ]
[ 72-19-5 ]
[ 73-32-5 ]
S-Adenosyl-L-methionine [ No CAS ]
(3S,6R,9S,12R,15S,18R)-3-((S)-sec-Butyl)-9,15-bis-((R)-1-hydroxy-ethyl)-6,12,18-triisopropyl-4,10,16-trimethyl-1,7,13-trioxa-4,10,16-triaza-cyclooctadecane-2,5,8,11,14,17-hexaone [ No CAS ]
(3S,6R,9S,12R,15S,18R)-3,9-Bis-((S)-sec-butyl)-15-((R)-1-hydroxy-ethyl)-6,12,18-triisopropyl-4,10,16-trimethyl-1,7,13-trioxa-4,10,16-triaza-cyclooctadecane-2,5,8,11,14,17-hexaone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With enniatin synthetase from Fusarium sambucinum BBA 63933; ATP; magnesium chloride In water; glycerol at 27℃; for 0.5h;

Reference： [1]Krause; Lindemann; Glinski; Hornbogen; Bonse; Jeschke; Thielking; Gau; Kleinkauf; Zocher [Journal of Antibiotics, 2001, vol. 54, # 10, p. 797 - 804]

20
[ 17407-56-6 ]
C₃₅H₂₆Cl₂N₆O₄ [ No CAS ]
C₄₀H₃₄Cl₂N₆O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25℃;

Reference： [1]Nicolaou; Bella, Marco; Chen, David Y.-K.; Huang, Xianhai; Ling, Taotao; Snyder, Scott A. [Angewandte Chemie - International Edition, 2002, vol. 41, # 18, p. 3495 - 3499]

21
[ 17407-56-6 ]
[ 640281-52-3 ]
C-37 epi-diazonamide A [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.8 mg	With sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25℃; for 12h;

Reference： [1]Nicolaou; Chen, David Y.-K.; Huang, Xianhai; Ling, Taotao; Bella, Marco; Snyder, Scott A. [Journal of the American Chemical Society, 2004, vol. 126, # 40, p. 12888 - 12896]

22
[ 17407-56-6 ]
[ 42417-65-2 ]
[ 18668-12-7 ]

Reference： [1]Organic Letters,2004,vol. 6,p. 4615 - 4617

23
[ 17407-56-6 ]
[ 13850-91-4 ]
(R)-2-(tert-Butoxycarbonyl-methyl-amino)-3-methyl-butyric acid (R)-1-carboxy-2-methyl-propyl ester [ No CAS ]

Reference： [1]Organic Letters,2004,vol. 6,p. 4615 - 4617

24
[ 17407-56-6 ]
[ 20439-47-8 ]
(R)-2-Hydroxy-N-[(1R,2R)-2-((R)-2-hydroxy-3-methyl-butyrylamino)-cyclohexyl]-3-methyl-butyramide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: (R)-2-Hydroxy-3-methylbutyric acid With benzotriazol-1-ol; 1,1'-carbonyldiimidazole In tetrahydrofuran for 1h; Stage #2: (1R,2R)-1,2-diaminocyclohexane In tetrahydrofuran at 20℃; for 24h;

Reference： [1]Cobb, Alexander J.A.; Marson, Charles M. [Tetrahedron, 2005, vol. 61, # 5, p. 1269 - 1279]

25
[ 17407-55-5 ]
[ 17407-56-6 ]

Yield	Reaction Conditions	Operation in experiment
	With BIS-TRIS buffer; Lactobacillus paracasei DSM 20207 In water at 42℃; for 24h;

Reference： [1]Glueck, Silvia M.; Pirker, Monika; Nestl, Bettina M.; Ueberbacher, Barbara T.; Larissegger-Schnell, Barbara; Csar, Katrin; Hauer, Bernhard; Stuermer, Rainer; Kroutil, Wolfgang; Faber, Kurt [Journal of Organic Chemistry, 2005, vol. 70, # 10, p. 4028 - 4032]

26
[ 107-18-6 ]
[ 421545-80-4 ]
(R)-allyl-2-hydroxy-3-methylbutanoate [ No CAS ]
[ 17407-56-6 ]
[ 17407-55-5 ]
[ 178113-56-9 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: allyl alcohol; 5-isopropyl-[1,3]dioxolane-2,4-dione With hydroquinidine anthraquinone-1,4-diyl diether In diethyl ether at -78℃; for 6h; Stage #2: With water Further stages. Title compound not separated from byproducts.;

Reference： [1]Tang, Liang; Deng, Li [Journal of the American Chemical Society, 2002, vol. 124, # 12, p. 2870 - 2871]

27
[ 17407-56-6 ]
[ 100-39-0 ]
benzyl (R)-2-hydroxy-3-methylbutanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: (R)-2-Hydroxy-3-methylbutyric acid With caesium carbonate In N,N-dimethyl-formamide at 0℃; for 0.666667h; Inert atmosphere; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 0 - 20℃; for 15h; Inert atmosphere;
58%	Stage #1: (R)-2-Hydroxy-3-methylbutyric acid With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: benzyl bromide In N,N-dimethyl-formamide Inert atmosphere;	Benzyl (2R)-2-hydroxy-3-methylbutanoate (7) To a (2R)-2-hydroxy-3-methylbutanoic acid (2.95 g, 25 mmol) in dry DMF (17mL, 1.5M) is slowly added powdered Cs2CO3 (4.0 g, 0.5 eq) in portions at roomtemperature. The mixture was allowed to stir for 30 min. before the addition ofbenzyl bromide (3.3 mL, 1.1 eq). The mixture was allowed to stir overnightbefore the reaction mixture was filtered, washing with 20% EtOAc/40-60petroleum ether (100 mL). The filtrate was washed with aq. half-saturatedNH4Cl solution (3 x 50 mL), half sat. NaHCO3 (1 x 50 mL), and the organic layers werecombined and concentrated in vacuo. Residual benzyl alcohol was removed by azeotropic rotaryvacuum distillation with H2O (2 x 25 mL), and the organic residue was azeotropically dried with toluene (25 mL). The resulting oil (3.0g, 58% yield) was sufficiently pure for the next step. Ananalytically pure sample could be obtained by flash column chromatography (silica gel, 5% to10% EtOAc/40-60 petroleum ether).
	With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile

	With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20℃; for 24h;
1.3 g	With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃; for 16h;	a DBU (1.021 niL, 6.77 mmol) was added to a solution of (R)-2-hydroxy-3- methylbutanoic acid (0.8 g, 6.77 mmol) and benzyl bromide (1.390 g, 8.13 mmol) in DMF (10 mL) and the resulting yellowish solution was stirred at rt for 16 h. The mixture was then taken up in EtOAc (50 mL) and water (30 ml) and the organic layer was separated. The aqueous layer was extracted with EtOAc and the combined organic layers were washed with brine, dried (MgS04), filtered and concentrated to give a clear oil. The residue was purified by flash chromatography (10%EtOAc/Hexanes). A clear oil corresponding to Cap L-32 step a (1.3 g) was recovered. NMR (400MHz, CDCI3) δ 7.44 - 7.31 (m, 5H), 5.30 - 5.17 (m, 2H), 4.10 (dd, J=6.1, 3.4 Hz, 1H), 2.73 (dd, J=6.1, 1.9 Hz, 1H), 2.11 (dtd, J=13.8, 6.9, 3.5 Hz, 1H), 1.02 (d, J=7.0 Hz, 3H), 0.84 (d, J=7.0 Hz, 3H);13C NMR (101MHz, CDCI3) δ 174.8, 135.2, 128.6 (s, 2C), 128.5, 128.4 (s, 2C), 75.0, 67.3, 32.2, 18.8, 15.9
	With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃; for 64h;	B1.a a) (R)-benzy 2-hydroxy-3-methybutanoate To D-apha-hydroxyisovaeric acid (5 g, 42.3 rnmoD in DMF (50 mD were added benzybromide (6.00 m, 50.8 mmd) and DBU (6.38 m, 42.3 mmd) and the reaction mixture was stirred for 64h at RT. The sdvent was evaporated and the residue was taken up in AcOEt/water. The organic phase was dried over Na2SO4, fHtered and evaporated. The crude product was purified by flash cdumn chromatography on sHica g& (cyciohexane/AcOEt: 1/0 to 9/1) to afford (R)-benzy 2-hydroxy-3-methybutanoate. M/z = 209 [M+H]+, Rt = 0.95 mm (UPLC Method B2), 1H NMR (400 MHz, DMSO-d3) O ppm: 746-7.29 (rn, 5H), 5.35 (d, IH), 5.14 (d, 2H), 3.87 (dd, IH), 2.00-190 (m, IH), 088 (d. 3H). 0.82 (d, 3H).

Reference： [1]Lücke, Daniel; Dalton, Toryn; Ley, Steven V.; Wilson, Zoe E. [Chemistry - A European Journal, 2016, vol. 22, # 12, p. 4206 - 4217]
[2]Hu, Dennis X.; Bielitza, Max; Koos, Peter; Ley, Steven V. [Tetrahedron Letters, 2012, vol. 53, # 32, p. 4077 - 4079]
[3]Uesusuki, Shinya; Watanabe, Bunta; Yamamoto, Shuji; Otsuki, Junko; Nakagawa, Yoshiaki; Miyagawa, Hisashi [Bioscience, Biotechnology and Biochemistry, 2004, vol. 68, # 5, p. 1097 - 1105]
[4]Location in patent: experimental part Braunagel, Julia; Junghans, Ann; Koeper, Ingo [Australian Journal of Chemistry, 2011, vol. 64, # 1, p. 54 - 61]
[5]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2015/5901, 2015, A1 Location in patent: Page/Page column 598
[6]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2015/181747, 2015, A1 Location in patent: Page/Page column 40

28
[ 67-56-1 ]
[ 17407-56-6 ]
[ 18107-18-1 ]
[ 90244-32-9 ]

Yield	Reaction Conditions	Operation in experiment
30%	In hexane at 0℃; for 1.33333h;	4 To a solution of (R)-2-hydroxy-3-methylbutanoic acid (5.0 gm, 42.2 mmol) in methanol was added a solution of TMS CH2N2 (2M) in hexane (65 mL), at 0° C., over 20 min. The reaction mixture was stirred at 0° C. for 1 h. The reaction was concentrated with a bath temperature of 20° C. and vacuum greater than 50 mm Hg. Purification via silica gel chromatography using 2-100% EtOAc in hexanes gave the ester as a yellow oil (438 mg, 12.7 mmol, 30% yield). 1H NMR (400 MHz, DMSO-d6) δ 5.30 (d, J=5.1 Hz, 1H), 3.81 (t, J=0.8 Hz, 1H), 3.63H), 1.94-1.86 (m, 1H), 0.88-0.82 (m, 6H).

Reference： [1]Current Patent Assignee: VERTEX PHARMACEUTICALS (OLD) - US2008/27067, 2008, A1 Location in patent: Page/Page column 285

29
[ 17407-56-6 ]
[ 812788-12-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: N,N'-carbonyldiimidazole / tetrahydrofuran / 4 h / 20 °C 1.2: 54 mg / tetrahydrofuran / 30 h / 20 °C 2.1: 100 percent / H₂ / Pd/C / methanol / 2 h 3.1: 2-chloro-1-methylpyridinium iodide; triethylamine / CH₂Cl₂ / 4 h / Heating

Reference： [1]Pedras, M. Soledade C.; Chumala, Paulos B.; Wilson Quail [Organic Letters, 2004, vol. 6, # 24, p. 4615 - 4617]

30
[ 17407-56-6 ]
[ 812788-38-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: N,N'-carbonyldiimidazole / tetrahydrofuran / 4 h / 20 °C 1.2: 54 mg / tetrahydrofuran / 30 h / 20 °C 2.1: 100 percent / H₂ / Pd/C / methanol / 2 h

Reference： [1]Pedras, M. Soledade C.; Chumala, Paulos B.; Wilson Quail [Organic Letters, 2004, vol. 6, # 24, p. 4615 - 4617]

31
[ 17407-56-6 ]
(2S,3S,4R)-2-hydroxy-3-methyl-4-iso-propyl-4-butyrolactone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1.1: 85 percent / iPr₂NEt / CH₂Cl₂ / 52 h / 20 °C 2.1: 87 percent / DIBAL-H / tetrahydrofuran / 3 h / 0 °C 3.1: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / -55 - 130 °C 4.1: 7.0 g / CH₂Cl₂ / 14 h / 20 °C 5.1: 90 percent / TMSCl / tetrahydrofuran; diethyl ether / 3.5 h / -78 °C 6.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C 6.2: 80 percent / trans-2-phenyl-sulfonyl-3-phenyloxaziridine / tetrahydrofuran; toluene / 3 h / -78 °C 7.1: H₂ / Pd(OH)2/C / methanol / 0.75 h / 2327.23 Torr

Reference： [1]Hanessian; Ma; Wang [Journal of the American Chemical Society, 2001, vol. 123, # 42, p. 10200 - 10206]

32
[ 17407-56-6 ]
[ 906534-74-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 85 percent / iPr₂NEt / CH₂Cl₂ / 52 h / 20 °C 2: 87 percent / DIBAL-H / tetrahydrofuran / 3 h / 0 °C 3: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / -55 - 130 °C

Reference： [1]Hanessian; Ma; Wang [Journal of the American Chemical Society, 2001, vol. 123, # 42, p. 10200 - 10206]

33
[ 17407-56-6 ]
[ 381247-05-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 85 percent / iPr₂NEt / CH₂Cl₂ / 52 h / 20 °C

Reference： [1]Hanessian; Ma; Wang [Journal of the American Chemical Society, 2001, vol. 123, # 42, p. 10200 - 10206]

34
[ 17407-56-6 ]
[ 381247-06-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 85 percent / iPr₂NEt / CH₂Cl₂ / 52 h / 20 °C 2: 87 percent / DIBAL-H / tetrahydrofuran / 3 h / 0 °C

Reference： [1]Hanessian; Ma; Wang [Journal of the American Chemical Society, 2001, vol. 123, # 42, p. 10200 - 10206]

35
[ 17407-56-6 ]
[ 381246-75-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 85 percent / iPr₂NEt / CH₂Cl₂ / 52 h / 20 °C 2: 87 percent / DIBAL-H / tetrahydrofuran / 3 h / 0 °C 3: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / -55 - 130 °C 4: 7.0 g / CH₂Cl₂ / 14 h / 20 °C

Reference： [1]Hanessian; Ma; Wang [Journal of the American Chemical Society, 2001, vol. 123, # 42, p. 10200 - 10206]

36
[ 17407-56-6 ]
[ 381246-76-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 85 percent / iPr₂NEt / CH₂Cl₂ / 52 h / 20 °C 2: 87 percent / DIBAL-H / tetrahydrofuran / 3 h / 0 °C 3: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / -55 - 130 °C 4: 7.0 g / CH₂Cl₂ / 14 h / 20 °C 5: 90 percent / TMSCl / tetrahydrofuran; diethyl ether / 3.5 h / -78 °C

Reference： [1]Hanessian; Ma; Wang [Journal of the American Chemical Society, 2001, vol. 123, # 42, p. 10200 - 10206]

37
[ 17407-56-6 ]
[ 183201-71-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: 85 percent / iPr₂NEt / CH₂Cl₂ / 52 h / 20 °C 2.1: 87 percent / DIBAL-H / tetrahydrofuran / 3 h / 0 °C 3.1: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / -55 - 130 °C 4.1: 7.0 g / CH₂Cl₂ / 14 h / 20 °C 5.1: 90 percent / TMSCl / tetrahydrofuran; diethyl ether / 3.5 h / -78 °C 6.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C 6.2: 80 percent / trans-2-phenyl-sulfonyl-3-phenyloxaziridine / tetrahydrofuran; toluene / 3 h / -78 °C

Reference： [1]Hanessian; Ma; Wang [Journal of the American Chemical Society, 2001, vol. 123, # 42, p. 10200 - 10206]

38
[ 17407-56-6 ]
2,2-Dimethyl-propionic acid (2S,3R,4R)-2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-3,5-dimethyl-hexyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 11 steps 1.1: 85 percent / iPr₂NEt / CH₂Cl₂ / 52 h / 20 °C 2.1: 87 percent / DIBAL-H / tetrahydrofuran / 3 h / 0 °C 3.1: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / -55 - 130 °C 4.1: 7.0 g / CH₂Cl₂ / 14 h / 20 °C 5.1: 90 percent / TMSCl / tetrahydrofuran; diethyl ether / 3.5 h / -78 °C 6.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C 6.2: 80 percent / trans-2-phenyl-sulfonyl-3-phenyloxaziridine / tetrahydrofuran; toluene / 3 h / -78 °C 7.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C 8.1: 86 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / 0 °C 9.1: 88 percent / DMAP / CH₂Cl₂ / 12 h / 0 °C 10.1: H₂ / Pd(OH)2/C / methanol / 6 h / 20 °C / 760.05 Torr

Reference： [1]Hanessian; Ma; Wang [Journal of the American Chemical Society, 2001, vol. 123, # 42, p. 10200 - 10206]

39
[ 17407-56-6 ]
[ 381247-09-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 13 steps 1.1: 85 percent / iPr₂NEt / CH₂Cl₂ / 52 h / 20 °C 2.1: 87 percent / DIBAL-H / tetrahydrofuran / 3 h / 0 °C 3.1: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / -55 - 130 °C 4.1: 7.0 g / CH₂Cl₂ / 14 h / 20 °C 5.1: 90 percent / TMSCl / tetrahydrofuran; diethyl ether / 3.5 h / -78 °C 6.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C 6.2: 80 percent / trans-2-phenyl-sulfonyl-3-phenyloxaziridine / tetrahydrofuran; toluene / 3 h / -78 °C 7.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C 8.1: 86 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / 0 °C 9.1: 88 percent / DMAP / CH₂Cl₂ / 12 h / 0 °C 10.1: H₂ / Pd(OH)2/C / methanol / 6 h / 20 °C / 760.05 Torr 11.1: 2.86 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C 12.1: 91 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / -78 °C

Reference： [1]Hanessian; Ma; Wang [Journal of the American Chemical Society, 2001, vol. 123, # 42, p. 10200 - 10206]

40
[ 17407-56-6 ]
[ 381247-08-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1.1: 85 percent / iPr₂NEt / CH₂Cl₂ / 52 h / 20 °C 2.1: 87 percent / DIBAL-H / tetrahydrofuran / 3 h / 0 °C 3.1: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / -55 - 130 °C 4.1: 7.0 g / CH₂Cl₂ / 14 h / 20 °C 5.1: 90 percent / TMSCl / tetrahydrofuran; diethyl ether / 3.5 h / -78 °C 6.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C 6.2: 80 percent / trans-2-phenyl-sulfonyl-3-phenyloxaziridine / tetrahydrofuran; toluene / 3 h / -78 °C 7.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C 8.1: 86 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / 0 °C

Reference： [1]Hanessian; Ma; Wang [Journal of the American Chemical Society, 2001, vol. 123, # 42, p. 10200 - 10206]

41
[ 17407-56-6 ]
[ 381247-07-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1.1: 85 percent / iPr₂NEt / CH₂Cl₂ / 52 h / 20 °C 2.1: 87 percent / DIBAL-H / tetrahydrofuran / 3 h / 0 °C 3.1: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / -55 - 130 °C 4.1: 7.0 g / CH₂Cl₂ / 14 h / 20 °C 5.1: 90 percent / TMSCl / tetrahydrofuran; diethyl ether / 3.5 h / -78 °C 6.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C 6.2: 80 percent / trans-2-phenyl-sulfonyl-3-phenyloxaziridine / tetrahydrofuran; toluene / 3 h / -78 °C 7.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

Reference： [1]Hanessian; Ma; Wang [Journal of the American Chemical Society, 2001, vol. 123, # 42, p. 10200 - 10206]

42
[ 17407-56-6 ]
[ 381246-79-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 14 steps 1.1: 85 percent / iPr₂NEt / CH₂Cl₂ / 52 h / 20 °C 2.1: 87 percent / DIBAL-H / tetrahydrofuran / 3 h / 0 °C 3.1: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / -55 - 130 °C 4.1: 7.0 g / CH₂Cl₂ / 14 h / 20 °C 5.1: 90 percent / TMSCl / tetrahydrofuran; diethyl ether / 3.5 h / -78 °C 6.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C 6.2: 80 percent / trans-2-phenyl-sulfonyl-3-phenyloxaziridine / tetrahydrofuran; toluene / 3 h / -78 °C 7.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C 8.1: 86 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / 0 °C 9.1: 88 percent / DMAP / CH₂Cl₂ / 12 h / 0 °C 10.1: H₂ / Pd(OH)2/C / methanol / 6 h / 20 °C / 760.05 Torr 11.1: 2.86 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C 12.1: 91 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / -78 °C 13.1: 84 percent / I₂; imidazole; PPh₃ / toluene / 1.5 h / 0 °C

Reference： [1]Hanessian; Ma; Wang [Journal of the American Chemical Society, 2001, vol. 123, # 42, p. 10200 - 10206]

43
[ 17407-56-6 ]
[ 381246-78-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 12 steps 1.1: 85 percent / iPr₂NEt / CH₂Cl₂ / 52 h / 20 °C 2.1: 87 percent / DIBAL-H / tetrahydrofuran / 3 h / 0 °C 3.1: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / -55 - 130 °C 4.1: 7.0 g / CH₂Cl₂ / 14 h / 20 °C 5.1: 90 percent / TMSCl / tetrahydrofuran; diethyl ether / 3.5 h / -78 °C 6.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C 6.2: 80 percent / trans-2-phenyl-sulfonyl-3-phenyloxaziridine / tetrahydrofuran; toluene / 3 h / -78 °C 7.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C 8.1: 86 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / 0 °C 9.1: 88 percent / DMAP / CH₂Cl₂ / 12 h / 0 °C 10.1: H₂ / Pd(OH)2/C / methanol / 6 h / 20 °C / 760.05 Torr 11.1: 2.86 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

Reference： [1]Hanessian; Ma; Wang [Journal of the American Chemical Society, 2001, vol. 123, # 42, p. 10200 - 10206]

44
[ 17407-56-6 ]
[ 381246-77-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1.1: 85 percent / iPr₂NEt / CH₂Cl₂ / 52 h / 20 °C 2.1: 87 percent / DIBAL-H / tetrahydrofuran / 3 h / 0 °C 3.1: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / -55 - 130 °C 4.1: 7.0 g / CH₂Cl₂ / 14 h / 20 °C 5.1: 90 percent / TMSCl / tetrahydrofuran; diethyl ether / 3.5 h / -78 °C 6.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C 6.2: 80 percent / trans-2-phenyl-sulfonyl-3-phenyloxaziridine / tetrahydrofuran; toluene / 3 h / -78 °C 7.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C 8.1: 86 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / 0 °C 9.1: 88 percent / DMAP / CH₂Cl₂ / 12 h / 0 °C

Reference： [1]Hanessian; Ma; Wang [Journal of the American Chemical Society, 2001, vol. 123, # 42, p. 10200 - 10206]

45
[ 17407-56-6 ]
[ 381246-84-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 17 steps 1.1: 85 percent / iPr₂NEt / CH₂Cl₂ / 52 h / 20 °C 2.1: 87 percent / DIBAL-H / tetrahydrofuran / 3 h / 0 °C 3.1: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / -55 - 130 °C 4.1: 7.0 g / CH₂Cl₂ / 14 h / 20 °C 5.1: 90 percent / TMSCl / tetrahydrofuran; diethyl ether / 3.5 h / -78 °C 6.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C 6.2: 80 percent / trans-2-phenyl-sulfonyl-3-phenyloxaziridine / tetrahydrofuran; toluene / 3 h / -78 °C 7.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C 8.1: 86 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / 0 °C 9.1: 88 percent / DMAP / CH₂Cl₂ / 12 h / 0 °C 10.1: H₂ / Pd(OH)2/C / methanol / 6 h / 20 °C / 760.05 Torr 11.1: 2.86 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C 12.1: 91 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / -78 °C 13.1: 84 percent / I₂; imidazole; PPh₃ / toluene / 1.5 h / 0 °C 14.1: t-BuLi; HMPA / tetrahydrofuran; pentane / 1 h / -78 °C 14.2: 81 percent / tetrahydrofuran; pentane / 2 h / -78 °C 15.1: 91 percent / TBAF; AcOH / tetrahydrofuran / 9 h 16.1: 91 percent / DMSO; Et₃N; SO₃*Py / CH₂Cl₂ / 2 h / 20 °C

Reference： [1]Hanessian; Ma; Wang [Journal of the American Chemical Society, 2001, vol. 123, # 42, p. 10200 - 10206]

46
[ 17407-56-6 ]
[ 381247-20-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 16 steps 1.1: 85 percent / iPr₂NEt / CH₂Cl₂ / 52 h / 20 °C 2.1: 87 percent / DIBAL-H / tetrahydrofuran / 3 h / 0 °C 3.1: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / -55 - 130 °C 4.1: 7.0 g / CH₂Cl₂ / 14 h / 20 °C 5.1: 90 percent / TMSCl / tetrahydrofuran; diethyl ether / 3.5 h / -78 °C 6.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C 6.2: 80 percent / trans-2-phenyl-sulfonyl-3-phenyloxaziridine / tetrahydrofuran; toluene / 3 h / -78 °C 7.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C 8.1: 86 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / 0 °C 9.1: 88 percent / DMAP / CH₂Cl₂ / 12 h / 0 °C 10.1: H₂ / Pd(OH)2/C / methanol / 6 h / 20 °C / 760.05 Torr 11.1: 2.86 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C 12.1: 91 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / -78 °C 13.1: 84 percent / I₂; imidazole; PPh₃ / toluene / 1.5 h / 0 °C 14.1: t-BuLi; HMPA / tetrahydrofuran; pentane / 1 h / -78 °C 14.2: 81 percent / tetrahydrofuran; pentane / 2 h / -78 °C 15.1: 91 percent / TBAF; AcOH / tetrahydrofuran / 9 h

Reference： [1]Hanessian; Ma; Wang [Journal of the American Chemical Society, 2001, vol. 123, # 42, p. 10200 - 10206]

47
[ 17407-56-6 ]
[ 381247-22-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 22 steps 1.1: 85 percent / iPr₂NEt / CH₂Cl₂ / 52 h / 20 °C 2.1: 87 percent / DIBAL-H / tetrahydrofuran / 3 h / 0 °C 3.1: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / -55 - 130 °C 4.1: 7.0 g / CH₂Cl₂ / 14 h / 20 °C 5.1: 90 percent / TMSCl / tetrahydrofuran; diethyl ether / 3.5 h / -78 °C 6.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C 6.2: 80 percent / trans-2-phenyl-sulfonyl-3-phenyloxaziridine / tetrahydrofuran; toluene / 3 h / -78 °C 7.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C 8.1: 86 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / 0 °C 9.1: 88 percent / DMAP / CH₂Cl₂ / 12 h / 0 °C 10.1: H₂ / Pd(OH)2/C / methanol / 6 h / 20 °C / 760.05 Torr 11.1: 2.86 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C 12.1: 91 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / -78 °C 13.1: 84 percent / I₂; imidazole; PPh₃ / toluene / 1.5 h / 0 °C 14.1: t-BuLi; HMPA / tetrahydrofuran; pentane / 1 h / -78 °C 14.2: 81 percent / tetrahydrofuran; pentane / 2 h / -78 °C 15.1: 91 percent / TBAF; AcOH / tetrahydrofuran / 9 h 16.1: 91 percent / DMSO; Et₃N; SO₃*Py / CH₂Cl₂ / 2 h / 20 °C 17.1: 38 percent / tetrahydrofuran / 1 h / -20 °C 18.1: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 1.5 h 19.1: 93 percent / Super-Hydride / CH₂Cl₂; tetrahydrofuran / 2 h / -78 °C 20.1: t-BuOK / tetrahydrofuran / 0.5 h / -20 °C 20.2: 86 percent / t-BuOK / tetrahydrofuran / 1 h / -20 °C 21.1: 86 percent / CSA / methanol / 2 h
	Multi-step reaction with 20 steps 1.1: 85 percent / iPr₂NEt / CH₂Cl₂ / 52 h / 20 °C 2.1: 87 percent / DIBAL-H / tetrahydrofuran / 3 h / 0 °C 3.1: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / -55 - 130 °C 4.1: 7.0 g / CH₂Cl₂ / 14 h / 20 °C 5.1: 90 percent / TMSCl / tetrahydrofuran; diethyl ether / 3.5 h / -78 °C 6.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C 6.2: 80 percent / trans-2-phenyl-sulfonyl-3-phenyloxaziridine / tetrahydrofuran; toluene / 3 h / -78 °C 7.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C 8.1: 86 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / 0 °C 9.1: 88 percent / DMAP / CH₂Cl₂ / 12 h / 0 °C 10.1: H₂ / Pd(OH)2/C / methanol / 6 h / 20 °C / 760.05 Torr 11.1: 2.86 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C 12.1: 91 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / -78 °C 13.1: 84 percent / I₂; imidazole; PPh₃ / toluene / 1.5 h / 0 °C 14.1: t-BuLi; HMPA / tetrahydrofuran; pentane / 1 h / -78 °C 14.2: 81 percent / tetrahydrofuran; pentane / 2 h / -78 °C 15.1: 91 percent / TBAF; AcOH / tetrahydrofuran / 9 h 16.1: 91 percent / DMSO; Et₃N; SO₃*Py / CH₂Cl₂ / 2 h / 20 °C 17.1: 50 percent / tetrahydrofuran / 1 h / -20 °C 18.1: t-BuOK / tetrahydrofuran / 0.5 h / -20 °C 18.2: 86 percent / t-BuOK / tetrahydrofuran / 1 h / -20 °C 19.1: 86 percent / CSA / methanol / 2 h

Reference： [1]Hanessian; Ma; Wang [Journal of the American Chemical Society, 2001, vol. 123, # 42, p. 10200 - 10206]
[2]Hanessian; Ma; Wang [Journal of the American Chemical Society, 2001, vol. 123, # 42, p. 10200 - 10206]

48
[ 17407-56-6 ]
[ 381246-71-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 19 steps 1.1: 85 percent / iPr₂NEt / CH₂Cl₂ / 52 h / 20 °C 2.1: 87 percent / DIBAL-H / tetrahydrofuran / 3 h / 0 °C 3.1: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / -55 - 130 °C 4.1: 7.0 g / CH₂Cl₂ / 14 h / 20 °C 5.1: 90 percent / TMSCl / tetrahydrofuran; diethyl ether / 3.5 h / -78 °C 6.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C 6.2: 80 percent / trans-2-phenyl-sulfonyl-3-phenyloxaziridine / tetrahydrofuran; toluene / 3 h / -78 °C 7.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C 8.1: 86 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / 0 °C 9.1: 88 percent / DMAP / CH₂Cl₂ / 12 h / 0 °C 10.1: H₂ / Pd(OH)2/C / methanol / 6 h / 20 °C / 760.05 Torr 11.1: 2.86 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C 12.1: 91 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / -78 °C 13.1: 84 percent / I₂; imidazole; PPh₃ / toluene / 1.5 h / 0 °C 14.1: t-BuLi; HMPA / tetrahydrofuran; pentane / 1 h / -78 °C 14.2: 81 percent / tetrahydrofuran; pentane / 2 h / -78 °C 15.1: 91 percent / TBAF; AcOH / tetrahydrofuran / 9 h 16.1: 91 percent / DMSO; Et₃N; SO₃*Py / CH₂Cl₂ / 2 h / 20 °C 17.1: 38 percent / tetrahydrofuran / 1 h / -20 °C 18.1: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 1.5 h

Reference： [1]Hanessian; Ma; Wang [Journal of the American Chemical Society, 2001, vol. 123, # 42, p. 10200 - 10206]

49
[ 17407-56-6 ]
[ 381246-87-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 21 steps 1.1: 85 percent / iPr₂NEt / CH₂Cl₂ / 52 h / 20 °C 2.1: 87 percent / DIBAL-H / tetrahydrofuran / 3 h / 0 °C 3.1: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / -55 - 130 °C 4.1: 7.0 g / CH₂Cl₂ / 14 h / 20 °C 5.1: 90 percent / TMSCl / tetrahydrofuran; diethyl ether / 3.5 h / -78 °C 6.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C 6.2: 80 percent / trans-2-phenyl-sulfonyl-3-phenyloxaziridine / tetrahydrofuran; toluene / 3 h / -78 °C 7.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C 8.1: 86 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / 0 °C 9.1: 88 percent / DMAP / CH₂Cl₂ / 12 h / 0 °C 10.1: H₂ / Pd(OH)2/C / methanol / 6 h / 20 °C / 760.05 Torr 11.1: 2.86 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C 12.1: 91 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / -78 °C 13.1: 84 percent / I₂; imidazole; PPh₃ / toluene / 1.5 h / 0 °C 14.1: t-BuLi; HMPA / tetrahydrofuran; pentane / 1 h / -78 °C 14.2: 81 percent / tetrahydrofuran; pentane / 2 h / -78 °C 15.1: 91 percent / TBAF; AcOH / tetrahydrofuran / 9 h 16.1: 91 percent / DMSO; Et₃N; SO₃*Py / CH₂Cl₂ / 2 h / 20 °C 17.1: 38 percent / tetrahydrofuran / 1 h / -20 °C 18.1: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 1.5 h 19.1: 93 percent / Super-Hydride / CH₂Cl₂; tetrahydrofuran / 2 h / -78 °C 20.1: t-BuOK / tetrahydrofuran / 0.5 h / -20 °C 20.2: 86 percent / t-BuOK / tetrahydrofuran / 1 h / -20 °C
	Multi-step reaction with 19 steps 1.1: 85 percent / iPr₂NEt / CH₂Cl₂ / 52 h / 20 °C 2.1: 87 percent / DIBAL-H / tetrahydrofuran / 3 h / 0 °C 3.1: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / -55 - 130 °C 4.1: 7.0 g / CH₂Cl₂ / 14 h / 20 °C 5.1: 90 percent / TMSCl / tetrahydrofuran; diethyl ether / 3.5 h / -78 °C 6.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C 6.2: 80 percent / trans-2-phenyl-sulfonyl-3-phenyloxaziridine / tetrahydrofuran; toluene / 3 h / -78 °C 7.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C 8.1: 86 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / 0 °C 9.1: 88 percent / DMAP / CH₂Cl₂ / 12 h / 0 °C 10.1: H₂ / Pd(OH)2/C / methanol / 6 h / 20 °C / 760.05 Torr 11.1: 2.86 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C 12.1: 91 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / -78 °C 13.1: 84 percent / I₂; imidazole; PPh₃ / toluene / 1.5 h / 0 °C 14.1: t-BuLi; HMPA / tetrahydrofuran; pentane / 1 h / -78 °C 14.2: 81 percent / tetrahydrofuran; pentane / 2 h / -78 °C 15.1: 91 percent / TBAF; AcOH / tetrahydrofuran / 9 h 16.1: 91 percent / DMSO; Et₃N; SO₃*Py / CH₂Cl₂ / 2 h / 20 °C 17.1: 50 percent / tetrahydrofuran / 1 h / -20 °C 18.1: t-BuOK / tetrahydrofuran / 0.5 h / -20 °C 18.2: 86 percent / t-BuOK / tetrahydrofuran / 1 h / -20 °C

Reference： [1]Hanessian; Ma; Wang [Journal of the American Chemical Society, 2001, vol. 123, # 42, p. 10200 - 10206]
[2]Hanessian; Ma; Wang [Journal of the American Chemical Society, 2001, vol. 123, # 42, p. 10200 - 10206]

50
[ 17407-56-6 ]
[ 381246-85-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 18 steps 1.1: 85 percent / iPr₂NEt / CH₂Cl₂ / 52 h / 20 °C 2.1: 87 percent / DIBAL-H / tetrahydrofuran / 3 h / 0 °C 3.1: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / -55 - 130 °C 4.1: 7.0 g / CH₂Cl₂ / 14 h / 20 °C 5.1: 90 percent / TMSCl / tetrahydrofuran; diethyl ether / 3.5 h / -78 °C 6.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C 6.2: 80 percent / trans-2-phenyl-sulfonyl-3-phenyloxaziridine / tetrahydrofuran; toluene / 3 h / -78 °C 7.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C 8.1: 86 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / 0 °C 9.1: 88 percent / DMAP / CH₂Cl₂ / 12 h / 0 °C 10.1: H₂ / Pd(OH)2/C / methanol / 6 h / 20 °C / 760.05 Torr 11.1: 2.86 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C 12.1: 91 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / -78 °C 13.1: 84 percent / I₂; imidazole; PPh₃ / toluene / 1.5 h / 0 °C 14.1: t-BuLi; HMPA / tetrahydrofuran; pentane / 1 h / -78 °C 14.2: 81 percent / tetrahydrofuran; pentane / 2 h / -78 °C 15.1: 91 percent / TBAF; AcOH / tetrahydrofuran / 9 h 16.1: 91 percent / DMSO; Et₃N; SO₃*Py / CH₂Cl₂ / 2 h / 20 °C 17.1: 38 percent / tetrahydrofuran / 1 h / -20 °C

Reference： [1]Hanessian; Ma; Wang [Journal of the American Chemical Society, 2001, vol. 123, # 42, p. 10200 - 10206]

51
[ 17407-56-6 ]
[ 381246-86-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 20 steps 1.1: 85 percent / iPr₂NEt / CH₂Cl₂ / 52 h / 20 °C 2.1: 87 percent / DIBAL-H / tetrahydrofuran / 3 h / 0 °C 3.1: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / -55 - 130 °C 4.1: 7.0 g / CH₂Cl₂ / 14 h / 20 °C 5.1: 90 percent / TMSCl / tetrahydrofuran; diethyl ether / 3.5 h / -78 °C 6.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C 6.2: 80 percent / trans-2-phenyl-sulfonyl-3-phenyloxaziridine / tetrahydrofuran; toluene / 3 h / -78 °C 7.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C 8.1: 86 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / 0 °C 9.1: 88 percent / DMAP / CH₂Cl₂ / 12 h / 0 °C 10.1: H₂ / Pd(OH)2/C / methanol / 6 h / 20 °C / 760.05 Torr 11.1: 2.86 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C 12.1: 91 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / -78 °C 13.1: 84 percent / I₂; imidazole; PPh₃ / toluene / 1.5 h / 0 °C 14.1: t-BuLi; HMPA / tetrahydrofuran; pentane / 1 h / -78 °C 14.2: 81 percent / tetrahydrofuran; pentane / 2 h / -78 °C 15.1: 91 percent / TBAF; AcOH / tetrahydrofuran / 9 h 16.1: 91 percent / DMSO; Et₃N; SO₃*Py / CH₂Cl₂ / 2 h / 20 °C 17.1: 38 percent / tetrahydrofuran / 1 h / -20 °C 18.1: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 1.5 h 19.1: 93 percent / Super-Hydride / CH₂Cl₂; tetrahydrofuran / 2 h / -78 °C
	Multi-step reaction with 18 steps 1.1: 85 percent / iPr₂NEt / CH₂Cl₂ / 52 h / 20 °C 2.1: 87 percent / DIBAL-H / tetrahydrofuran / 3 h / 0 °C 3.1: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / -55 - 130 °C 4.1: 7.0 g / CH₂Cl₂ / 14 h / 20 °C 5.1: 90 percent / TMSCl / tetrahydrofuran; diethyl ether / 3.5 h / -78 °C 6.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C 6.2: 80 percent / trans-2-phenyl-sulfonyl-3-phenyloxaziridine / tetrahydrofuran; toluene / 3 h / -78 °C 7.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C 8.1: 86 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / 0 °C 9.1: 88 percent / DMAP / CH₂Cl₂ / 12 h / 0 °C 10.1: H₂ / Pd(OH)2/C / methanol / 6 h / 20 °C / 760.05 Torr 11.1: 2.86 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C 12.1: 91 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / -78 °C 13.1: 84 percent / I₂; imidazole; PPh₃ / toluene / 1.5 h / 0 °C 14.1: t-BuLi; HMPA / tetrahydrofuran; pentane / 1 h / -78 °C 14.2: 81 percent / tetrahydrofuran; pentane / 2 h / -78 °C 15.1: 91 percent / TBAF; AcOH / tetrahydrofuran / 9 h 16.1: 91 percent / DMSO; Et₃N; SO₃*Py / CH₂Cl₂ / 2 h / 20 °C 17.1: 50 percent / tetrahydrofuran / 1 h / -20 °C

Reference： [1]Hanessian; Ma; Wang [Journal of the American Chemical Society, 2001, vol. 123, # 42, p. 10200 - 10206]
[2]Hanessian; Ma; Wang [Journal of the American Chemical Society, 2001, vol. 123, # 42, p. 10200 - 10206]

52
[ 17407-56-6 ]
[ 381246-88-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 23 steps 1.1: 85 percent / iPr₂NEt / CH₂Cl₂ / 52 h / 20 °C 2.1: 87 percent / DIBAL-H / tetrahydrofuran / 3 h / 0 °C 3.1: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / -55 - 130 °C 4.1: 7.0 g / CH₂Cl₂ / 14 h / 20 °C 5.1: 90 percent / TMSCl / tetrahydrofuran; diethyl ether / 3.5 h / -78 °C 6.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C 6.2: 80 percent / trans-2-phenyl-sulfonyl-3-phenyloxaziridine / tetrahydrofuran; toluene / 3 h / -78 °C 7.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C 8.1: 86 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / 0 °C 9.1: 88 percent / DMAP / CH₂Cl₂ / 12 h / 0 °C 10.1: H₂ / Pd(OH)2/C / methanol / 6 h / 20 °C / 760.05 Torr 11.1: 2.86 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C 12.1: 91 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / -78 °C 13.1: 84 percent / I₂; imidazole; PPh₃ / toluene / 1.5 h / 0 °C 14.1: t-BuLi; HMPA / tetrahydrofuran; pentane / 1 h / -78 °C 14.2: 81 percent / tetrahydrofuran; pentane / 2 h / -78 °C 15.1: 91 percent / TBAF; AcOH / tetrahydrofuran / 9 h 16.1: 91 percent / DMSO; Et₃N; SO₃*Py / CH₂Cl₂ / 2 h / 20 °C 17.1: 38 percent / tetrahydrofuran / 1 h / -20 °C 18.1: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 1.5 h 19.1: 93 percent / Super-Hydride / CH₂Cl₂; tetrahydrofuran / 2 h / -78 °C 20.1: t-BuOK / tetrahydrofuran / 0.5 h / -20 °C 20.2: 86 percent / t-BuOK / tetrahydrofuran / 1 h / -20 °C 21.1: 86 percent / CSA / methanol / 2 h 22.1: 87 percent / DMAP / tetrahydrofuran; dimethylformamide / 18 h / 20 °C
	Multi-step reaction with 21 steps 1.1: 85 percent / iPr₂NEt / CH₂Cl₂ / 52 h / 20 °C 2.1: 87 percent / DIBAL-H / tetrahydrofuran / 3 h / 0 °C 3.1: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / -55 - 130 °C 4.1: 7.0 g / CH₂Cl₂ / 14 h / 20 °C 5.1: 90 percent / TMSCl / tetrahydrofuran; diethyl ether / 3.5 h / -78 °C 6.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C 6.2: 80 percent / trans-2-phenyl-sulfonyl-3-phenyloxaziridine / tetrahydrofuran; toluene / 3 h / -78 °C 7.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C 8.1: 86 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / 0 °C 9.1: 88 percent / DMAP / CH₂Cl₂ / 12 h / 0 °C 10.1: H₂ / Pd(OH)2/C / methanol / 6 h / 20 °C / 760.05 Torr 11.1: 2.86 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C 12.1: 91 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / -78 °C 13.1: 84 percent / I₂; imidazole; PPh₃ / toluene / 1.5 h / 0 °C 14.1: t-BuLi; HMPA / tetrahydrofuran; pentane / 1 h / -78 °C 14.2: 81 percent / tetrahydrofuran; pentane / 2 h / -78 °C 15.1: 91 percent / TBAF; AcOH / tetrahydrofuran / 9 h 16.1: 91 percent / DMSO; Et₃N; SO₃*Py / CH₂Cl₂ / 2 h / 20 °C 17.1: 50 percent / tetrahydrofuran / 1 h / -20 °C 18.1: t-BuOK / tetrahydrofuran / 0.5 h / -20 °C 18.2: 86 percent / t-BuOK / tetrahydrofuran / 1 h / -20 °C 19.1: 86 percent / CSA / methanol / 2 h 20.1: 87 percent / DMAP / tetrahydrofuran; dimethylformamide / 18 h / 20 °C

Reference： [1]Hanessian; Ma; Wang [Journal of the American Chemical Society, 2001, vol. 123, # 42, p. 10200 - 10206]
[2]Hanessian; Ma; Wang [Journal of the American Chemical Society, 2001, vol. 123, # 42, p. 10200 - 10206]

53
[ 17407-56-6 ]
[ 381246-83-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 15 steps 1.1: 85 percent / iPr₂NEt / CH₂Cl₂ / 52 h / 20 °C 2.1: 87 percent / DIBAL-H / tetrahydrofuran / 3 h / 0 °C 3.1: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / -55 - 130 °C 4.1: 7.0 g / CH₂Cl₂ / 14 h / 20 °C 5.1: 90 percent / TMSCl / tetrahydrofuran; diethyl ether / 3.5 h / -78 °C 6.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C 6.2: 80 percent / trans-2-phenyl-sulfonyl-3-phenyloxaziridine / tetrahydrofuran; toluene / 3 h / -78 °C 7.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C 8.1: 86 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / 0 °C 9.1: 88 percent / DMAP / CH₂Cl₂ / 12 h / 0 °C 10.1: H₂ / Pd(OH)2/C / methanol / 6 h / 20 °C / 760.05 Torr 11.1: 2.86 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C 12.1: 91 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / -78 °C 13.1: 84 percent / I₂; imidazole; PPh₃ / toluene / 1.5 h / 0 °C 14.1: t-BuLi; HMPA / tetrahydrofuran; pentane / 1 h / -78 °C 14.2: 81 percent / tetrahydrofuran; pentane / 2 h / -78 °C

Reference： [1]Hanessian; Ma; Wang [Journal of the American Chemical Society, 2001, vol. 123, # 42, p. 10200 - 10206]

54
[ 55109-47-2 ]
[ 17407-56-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 65 percent / Et₃N, DMAP / CH₂Cl₂ / 6 h / Ambient temperature 2: 75 percent / HCl / tetrahydrofuran; H₂O / 3 h / Ambient temperature 3: KBH₄ / methanol / 10 h / 0 °C 4: 58 percent / H₂SO₄ / H₂O / 0.5 h / 90 °C
	Multi-step reaction with 5 steps 1: Et₃N, DMAP / CH₂Cl₂ / 6 h / Ambient temperature 2: 98 percent / TFA / CH₂Cl₂ / 78 h / Heating 3: 99 percent / H₂ / Pd/C / ethyl acetate / 2.5 h / 2585.7 Torr 4: 51 percent / Na, liquid NH₃ / tetrahydrofuran / 0.01 h 5: 1M H₂SO₄ / 36 h / Heating
	Multi-step reaction with 5 steps 1: Et₃N, DMAP / CH₂Cl₂ / 6 h / Ambient temperature 2: TiCl₄ / -40 °C 3: 99 percent / H₂ / Pd/C / ethyl acetate / 2.5 h / 2585.7 Torr 4: 51 percent / Na, liquid NH₃ / tetrahydrofuran / 0.01 h 5: 1M H₂SO₄ / 36 h / Heating

Reference： [1]Pansare, Sunil V.; Ravi, R. Gnana [Tetrahedron, 1998, vol. 54, # 48, p. 14549 - 14564]
[2]Pansare, Sunil V.; Ravi, R.Gnana; Jain, Rajendra P. [Journal of Organic Chemistry, 1998, vol. 63, # 12, p. 4120 - 4124]
[3]Pansare, Sunil V.; Ravi, R.Gnana; Jain, Rajendra P. [Journal of Organic Chemistry, 1998, vol. 63, # 12, p. 4120 - 4124]

55
[ 759-05-7 ]
[ 17407-56-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: Cl₂CHOCH₃ / CH₂Cl₂ / 1.) room temperature, 20 min, 2.) 50-55 deg C, 30 min 2: Et₃N, DMAP / CH₂Cl₂ / 6 h / Ambient temperature 3: 98 percent / TFA / CH₂Cl₂ / 78 h / Heating 4: 99 percent / H₂ / Pd/C / ethyl acetate / 2.5 h / 2585.7 Torr 5: 51 percent / Na, liquid NH₃ / tetrahydrofuran / 0.01 h 6: 1M H₂SO₄ / 36 h / Heating
	Multi-step reaction with 6 steps 1: Cl₂CHOCH₃ / CH₂Cl₂ / 1.) room temperature, 20 min, 2.) 50-55 deg C, 30 min 2: Et₃N, DMAP / CH₂Cl₂ / 6 h / Ambient temperature 3: TiCl₄ / -40 °C 4: 99 percent / H₂ / Pd/C / ethyl acetate / 2.5 h / 2585.7 Torr 5: 51 percent / Na, liquid NH₃ / tetrahydrofuran / 0.01 h 6: 1M H₂SO₄ / 36 h / Heating

Reference： [1]Pansare, Sunil V.; Ravi, R.Gnana; Jain, Rajendra P. [Journal of Organic Chemistry, 1998, vol. 63, # 12, p. 4120 - 4124]
[2]Pansare, Sunil V.; Ravi, R.Gnana; Jain, Rajendra P. [Journal of Organic Chemistry, 1998, vol. 63, # 12, p. 4120 - 4124]

56
[ 207223-32-3 ]
[ 17407-56-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 99 percent / H₂ / Pd/C / ethyl acetate / 2.5 h / 2585.7 Torr 2: 51 percent / Na, liquid NH₃ / tetrahydrofuran / 0.01 h 3: 1M H₂SO₄ / 36 h / Heating

Reference： [1]Pansare, Sunil V.; Ravi, R.Gnana; Jain, Rajendra P. [Journal of Organic Chemistry, 1998, vol. 63, # 12, p. 4120 - 4124]

57
[ 207223-22-1 ]
[ 17407-56-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 98 percent / TFA / CH₂Cl₂ / 78 h / Heating 2: 99 percent / H₂ / Pd/C / ethyl acetate / 2.5 h / 2585.7 Torr 3: 51 percent / Na, liquid NH₃ / tetrahydrofuran / 0.01 h 4: 1M H₂SO₄ / 36 h / Heating
	Multi-step reaction with 4 steps 1: TiCl₄ / -40 °C 2: 99 percent / H₂ / Pd/C / ethyl acetate / 2.5 h / 2585.7 Torr 3: 51 percent / Na, liquid NH₃ / tetrahydrofuran / 0.01 h 4: 1M H₂SO₄ / 36 h / Heating

Reference： [1]Pansare, Sunil V.; Ravi, R.Gnana; Jain, Rajendra P. [Journal of Organic Chemistry, 1998, vol. 63, # 12, p. 4120 - 4124]
[2]Pansare, Sunil V.; Ravi, R.Gnana; Jain, Rajendra P. [Journal of Organic Chemistry, 1998, vol. 63, # 12, p. 4120 - 4124]

58
[ 17407-56-6 ]
indolactam V [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 78 percent / SOCl₂ / benzene / 40 h / Heating 2: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C 3: 78 percent / 2,6-lutidine / 1,2-dichloro-ethane / 18 h / 70 °C 4: H₂, (+)-camphorsulfonic acid / 10percent Pd/C / methanol / 7 h / 2585.7 Torr 5: hydroxybenzotriazole (HOBT), benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP), N-methylmorpholine (NMM) / N,N-dimethyl-acetamide / 64 h / Ambient temperature 6: sodium cyanoborohydride, AcOH / acetonitrile; H₂O / 1 h / 0 °C
	Multi-step reaction with 7 steps 1: 78 percent / SOCl₂ / benzene / 40 h / Heating 2: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C 3: 95 percent / proton sponge / 1,2-dichloro-ethane / 18 h / 70 °C 4: 73 percent / NaBH₄ / dimethylformamide; H₂O 5: H₂, (+)-camphorsulfonic acid / 10percent Pd/C / methanol / 7 h / 2585.7 Torr 6: hydroxybenzotriazole (HOBT), benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP), N-methylmorpholine (NMM) / N,N-dimethyl-acetamide / 64 h / Ambient temperature 7: sodium cyanoborohydride, AcOH / acetonitrile; H₂O / 1 h / 0 °C
	Multi-step reaction with 10 steps 1: thionyl chloride / benzene / 20 - 100 °C / Inert atmosphere 2: 2,6-dimethylpyridine / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 3: 2,6-dimethylpyridine / 1,2-dichloro-ethane / Inert atmosphere; Heating 4: toluene-4-sulfonic acid / Inert atmosphere 5: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 6: trifluoroacetic acid / dichloromethane / 6 h / 0 - 20 °C / Inert atmosphere 7: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 20 °C / 760.05 Torr 8: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 48 h / 20 °C / Inert atmosphere 9: sodium cyanoborohydride; acetic acid / water; acetonitrile / 0 - 20 °C / Inert atmosphere 10: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 0 - 20 °C / Inert atmosphere

Multi-step reaction with 11 steps 1: thionyl chloride / benzene / 20 - 100 °C / Inert atmosphere 2: 2,6-dimethylpyridine / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 3: 2,6-dimethylpyridine / 1,2-dichloro-ethane / Inert atmosphere; Heating 4: toluene-4-sulfonic acid / Inert atmosphere 5: triethylamine / acetonitrile / 20 °C 6: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 7: trifluoroacetic acid / dichloromethane / 6 h / 0 - 20 °C / Inert atmosphere 8: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 20 °C / 760.05 Torr 9: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 48 h / 20 °C / Inert atmosphere 10: sodium cyanoborohydride; acetic acid / water; acetonitrile / 0 - 20 °C / Inert atmosphere 11: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 0 - 20 °C / Inert atmosphere

Reference： [1]Kogan, Timothy P.; Somers, Todd C.; Venuti, Michael C. [Tetrahedron, 1990, vol. 46, # 19, p. 6623 - 6632]
[2]Kogan, Timothy P.; Somers, Todd C.; Venuti, Michael C. [Tetrahedron, 1990, vol. 46, # 19, p. 6623 - 6632]
[3]Stein, Jan; Stahn, Sonja; Neudörfl, Jörg-M.; Sperlich, Julia; Schmalz, Hans-Günther; Teusch, Nicole [ChemMedChem, 2018, vol. 13, # 2, p. 147 - 154]
[4]Stein, Jan; Stahn, Sonja; Neudörfl, Jörg-M.; Sperlich, Julia; Schmalz, Hans-Günther; Teusch, Nicole [ChemMedChem, 2018, vol. 13, # 2, p. 147 - 154]

59
[ 17407-56-6 ]
[ 90365-52-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 78 percent / SOCl₂ / benzene / 40 h / Heating 2: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C 3: 78 percent / 2,6-lutidine / 1,2-dichloro-ethane / 18 h / 70 °C 4: H₂, (+)-camphorsulfonic acid / 10percent Pd/C / methanol / 7 h / 2585.7 Torr 5: hydroxybenzotriazole (HOBT), benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP), N-methylmorpholine (NMM) / N,N-dimethyl-acetamide / 64 h / Ambient temperature
	Multi-step reaction with 6 steps 1: 78 percent / SOCl₂ / benzene / 40 h / Heating 2: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C 3: 95 percent / proton sponge / 1,2-dichloro-ethane / 18 h / 70 °C 4: 73 percent / NaBH₄ / dimethylformamide; H₂O 5: H₂, (+)-camphorsulfonic acid / 10percent Pd/C / methanol / 7 h / 2585.7 Torr 6: hydroxybenzotriazole (HOBT), benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP), N-methylmorpholine (NMM) / N,N-dimethyl-acetamide / 64 h / Ambient temperature
	Multi-step reaction with 8 steps 1: thionyl chloride / benzene / 20 - 100 °C / Inert atmosphere 2: 2,6-dimethylpyridine / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 3: 2,6-dimethylpyridine / 1,2-dichloro-ethane / 12 h / 85 °C / Inert atmosphere 4: toluene-4-sulfonic acid / 4 h / 20 °C / Inert atmosphere 5: trifluoroacetic acid / dichloromethane / 1.5 h / 0 °C / Inert atmosphere 6: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 20 °C / 760.05 Torr 7: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 °C / Inert atmosphere 8: L-Selectride / tetrahydrofuran / 85 °C / Inert atmosphere

Reference： [1]Kogan, Timothy P.; Somers, Todd C.; Venuti, Michael C. [Tetrahedron, 1990, vol. 46, # 19, p. 6623 - 6632]
[2]Kogan, Timothy P.; Somers, Todd C.; Venuti, Michael C. [Tetrahedron, 1990, vol. 46, # 19, p. 6623 - 6632]
[3]Stein, Jan; Stahn, Sonja; Neudörfl, Jörg-M.; Sperlich, Julia; Schmalz, Hans-Günther; Teusch, Nicole [ChemMedChem, 2018, vol. 13, # 2, p. 147 - 154]

60
[ 17407-56-6 ]
[ 131423-65-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 78 percent / SOCl₂ / benzene / 40 h / Heating 2: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C 3: 78 percent / 2,6-lutidine / 1,2-dichloro-ethane / 18 h / 70 °C 4: H₂, (+)-camphorsulfonic acid / 10percent Pd/C / methanol / 7 h / 2585.7 Torr
	Multi-step reaction with 5 steps 1: 78 percent / SOCl₂ / benzene / 40 h / Heating 2: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C 3: 95 percent / proton sponge / 1,2-dichloro-ethane / 18 h / 70 °C 4: 73 percent / NaBH₄ / dimethylformamide; H₂O 5: H₂, (+)-camphorsulfonic acid / 10percent Pd/C / methanol / 7 h / 2585.7 Torr

Reference： [1]Kogan, Timothy P.; Somers, Todd C.; Venuti, Michael C. [Tetrahedron, 1990, vol. 46, # 19, p. 6623 - 6632]
[2]Kogan, Timothy P.; Somers, Todd C.; Venuti, Michael C. [Tetrahedron, 1990, vol. 46, # 19, p. 6623 - 6632]

61
[ 17407-56-6 ]
[ 92148-07-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: Py 2: (i) PCl₅, (ii) /BRN= 3562296/, Et₃N 3: H₂ / Pd 4: N₂H₄*H₂O / ethanol / Heating
	Multi-step reaction with 4 steps 1: Py 2: (i) PCl₅, Et₂O, (ii) /BRN= 3562296/, Et₃N, THF 3: H₂ / PdO / ethanol 4: N₂H₄*H₂O / ethanol / Heating

Reference： [1]Shemyakin,M.M. et al. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1962, p. 2061 - 2067][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1962, p. 2154 - 2161]
[2]Shemyakin; Ovchinnkov; Ivanov; Kiryushkin [Tetrahedron, 1963, vol. 19, # 4, p. 581 - 591]

62
[ 17407-56-6 ]
[ 3339-53-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: Py 2: (i) PCl₅, (ii) /BRN= 3562296/, Et₃N 3: H₂ / Pd
	Multi-step reaction with 3 steps 1: Py 2: (i) PCl₅, Et₂O, (ii) /BRN= 3562296/, Et₃N, THF 3: H₂ / PdO / ethanol

Reference： [1]Shemyakin,M.M. et al. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1962, p. 2061 - 2067][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1962, p. 2154 - 2161]
[2]Shemyakin; Ovchinnkov; Ivanov; Kiryushkin [Tetrahedron, 1963, vol. 19, # 4, p. 581 - 591]

63
[ 17407-56-6 ]
[ 91824-42-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: Py 2: (i) PCl₅, (ii) /BRN= 3562296/, Et₃N 3: H₂ / Pd 4: NH₃ / methanol
	Multi-step reaction with 4 steps 1: Py 2: (i) PCl₅, Et₂O, (ii) /BRN= 3562296/, Et₃N, THF 3: H₂ / PdO / ethanol 4: NH₃ / methanol

Reference： [1]Shemyakin,M.M. et al. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1962, p. 2061 - 2067][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1962, p. 2154 - 2161]
[2]Shemyakin; Ovchinnkov; Ivanov; Kiryushkin [Tetrahedron, 1963, vol. 19, # 4, p. 581 - 591]

64
[ 17407-56-6 ]
[ 22838-60-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: HCl 2: (i) carbonyldiimidazole, THF, (ii) /BRN= 2525872/ 3: H₂ / Pd-C / tetrahydrofuran
	Multi-step reaction with 2 steps 1: HCl 2: (i) carbonyldiimidazole, (ii) H₂, Pd-BaSO₄
	Multi-step reaction with 3 steps 1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 24 h / 20 °C 2: dmap; dicyclohexyl-carbodiimide / dichloromethane / 12 h / -40 °C 3: palladium on activated charcoal; hydrogen / methanol / 3 h / 20 °C

Reference： [1]Losse,G.; Klengel,H. [Tetrahedron, 1971, vol. 27, p. 1423 - 1434]
[2]Gisin,B.F. et al. [Journal of the American Chemical Society, 1969, vol. 91, p. 2691 - 2695]
[3]Braunagel, Julia; Junghans, Ann; Koeper, Ingo [Australian Journal of Chemistry, 2011, vol. 64, # 1, p. 54 - 61]

65
[ 17407-56-6 ]
[ 32770-12-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: HCl 2: (i) carbonyldiimidazole, THF, (ii) /BRN= 2525872/ 3: H₂ / Pd-C / tetrahydrofuran 4: (i) carbonyldiimidazole, THF, (ii) /BRN= 2390203/ 5: HCl / acetic acid 6: (i) carbonyldiimidazole, THF, (ii) /BRN= 6129780/
	Multi-step reaction with 8 steps 1: HCl 2: (i) carbonyldiimidazole, THF, (ii) /BRN= 2525872/ 3: HCl / acetic acid / Ambient temperature 4: DCC / CH₂Cl₂ 5: HCl / acetic acid 6: (i) carbonyldiimidazole, THF, (ii) /BRN= 2390203/ 7: HCl / acetic acid 8: (i) carbonyldiimidazole, THF, (ii) /BRN= 6129780/

Reference： [1]Losse,G.; Klengel,H. [Tetrahedron, 1971, vol. 27, p. 1423 - 1434]
[2]Losse,G.; Klengel,H. [Tetrahedron, 1971, vol. 27, p. 1423 - 1434]

66
[ 17407-56-6 ]
H-L-Val-D-Hyv-D-Val-L-Lac-L-Val-D-Hyv-O-Benzyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: HCl 2: (i) carbonyldiimidazole, THF, (ii) /BRN= 2525872/ 3: H₂ / Pd-C / tetrahydrofuran 4: (i) carbonyldiimidazole, THF, (ii) /BRN= 2390203/ 5: HCl / acetic acid
	Multi-step reaction with 7 steps 1: HCl 2: (i) carbonyldiimidazole, THF, (ii) /BRN= 2525872/ 3: HCl / acetic acid / Ambient temperature 4: DCC / CH₂Cl₂ 5: HCl / acetic acid 6: (i) carbonyldiimidazole, THF, (ii) /BRN= 2390203/ 7: HCl / acetic acid

Reference： [1]Losse,G.; Klengel,H. [Tetrahedron, 1971, vol. 27, p. 1423 - 1434]
[2]Losse,G.; Klengel,H. [Tetrahedron, 1971, vol. 27, p. 1423 - 1434]

67
N-L-Prolyl-2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzylamide [ No CAS ]
[ 17407-56-6 ]
1-hydroxybenzotriazol-hydrate [ No CAS ]
N-(2R-Hydroxy-3-methylbutanoyl)-L-prolyl-2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine In ethyl acetate; N,N-dimethyl-formamide	61.3 Step 3 Step 3 To a stirred solution of L-prolyl-2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzylamide from the previous step (0.23 g, 0.62 mmol, HPLC RT=2.77 min), 2R-hydroxy-3-methylbutyric acid acid (77 mg, 0.65 mmol), and HOBT hydrate (99 mg, 0.65 mmol) in DMF (4 mL) was added EDC (0.16 g, 0.82 mmol). Diisopropylethylamine was then added in portions (0.1 mL total) to bring the pH of the solution to 6-7 as measured on wetted E. Merck pH indicator strips. The mixture was stirred at ambient temperature for 2 h, at which time HPLC analysis indicated complete consumption of the proline starting material. The DMF was removed under reduced pressure and the residue was partitioned between EtOAc (100 mL) and saturated aqueous NaHCO3 (50 mL). The EtOAc layer was separated, dried over anhydrous MgSO4, and filtered. The filtrate solvent was removed under reduced pressure and the residue was purified by flash chromatography using EtOAc as eluant. N-(2R-Hydroxy-3-methylbutanoyl)-L-prolyl-2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzylamide was obtained as a colorless gum (TLC Rf=0.7 (EtOAc); HPLC RT=3.21 min; LC-MS m/z=468).

Reference： [1]Current Patent Assignee: MERCK & CO INC - US2002/119992, 2002, A1

68
[Ru((-)-T-BINAP)](ClO₄)2 [ No CAS ]
[ 759-05-7 ]
[ 17407-56-6 ]

Yield	Reaction Conditions	Operation in experiment
	With nitrogen; In toluene;	EXAMPLE 3 In a 200 ml-volume autoclave whose atmosphere had been displaced with nitrogen were charged 11.5 g (0.1 mol) of 3-methyl-2-oxobutanoic acid and 100 ml of toluene, and 88 mg (0.090 mmol) of [Ru((-)-T-BINAP)](ClO4)2 as prepared in Reference Example 2 was added thereto to effect hydrogenation at a temperature of 60 C. and a hydrogen pressure of 50 kg/cm2 for 20 hours. After completion of the reaction, the solvent was removed by distillation, and the residue was extracted with an alkali. The aqueous layer was neutralized and extracted with diethyl ether. The extract was concentrated and dried to obtain 8 g of (R)-3-methyl-2-hydroxybutanoic acid having a melting point of 63 to 65 C. The optical rotation [alpha]D25 of the resulting alcohol was +10.65 (CHCl3). In the light of the optical rotation available in the literature, [alpha]D25 =+16.9 (CHCl3), the optical purity of the product was found to be 63%ee.

Reference： [1]Patent: US5066815,1991,A

69
[ 17407-56-6 ]
[ 31612-62-1 ]

Yield	Reaction Conditions	Operation in experiment
86.5%		4.a Production of (S)-1,2-Bis-(diphenylphosphino)-3-methyl-butane (a) (R)-1,2-Dihydroxy-3-methyl-butane was produced analogous to the S-isomer (see Example 3(a)) starting from (R)-2-hydroxy-isovaleric acid. The yield was 86.5% of theory Rotary value [α]D20 =-10.0° (c=1/CHCl3)

Reference： [1]Current Patent Assignee: EVONIK INDUSTRIES AG - US4356324, 1982, A

70
carriebowmide [ No CAS ]
[ 56-41-7 ]
[ 17407-56-6 ]
[ 3060-46-6 ]
[ 63-91-2 ]
[ 56564-52-4 ]

Reference： [1]Journal of Natural Products,2008,vol. 71,p. 2060 - 2063

71
[ 1187551-28-5 ]
[ 56-41-7 ]
[ 17407-56-6 ]
[ 17407-55-5 ]
[ 72-19-5 ]
[ 61-90-5 ]
[ 2812-32-0 ]
[ 56-84-8 ]
[ 56564-52-4 ]
[ 147-85-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; water at 110℃; for 24h;	2 A sample of compound 1 (100 μg) was treated with 6 N HCl at 110 0C for 24 h. The hydrolysate was concentrated to dryness, reconstituted in 100 μL H2O and then analyzed by chiral HPLC [column, Chirobiotic TAG (4.6 x 250 mm), Supelco; solvent, MeOH-10 mM NH4OAc (40:60, pH 5.23): flow rate, 0.5 niL/min; detection by ESIMS in positive ion mode (MRM scan)]. L-Thr, L-Leu, L-Pro, iV,iV-Me2-L-Val and iV-Me-D-Phe eluted at tR 7.2, 9.0, 14.4, 27.0 and 45.4 min, respectively. The retention times (fo, min; MRM ion pair, parent→product) of the authentic amino acids were as follows: L-Thr (7.2; 120→74), L-α//o-Thr (7.5), D-Thr (8.6;), D-α//o-Thr (11.9), L-Pro (14.4; 116→70), D-Pro (39.5), L-Leu (9.0; 132→86), D-Leu (20.6), N- Me-L-Phe (25.0; 180→134), iV-Me-D-Phe (45.4), A^iV-Me2-L- VaI (27.0; 146→100), and A^V-Me2-D-VaI (69.8). The assignment of L-Thr was confirmed by co-injection of the hydrolysate with L-α//o-Thr and L-Thr. The MS parameters used were as follows: DP 31.0, EP 8.0, CE 17.3, CXP 3.1, CUR 35, CAD Medium, IS 4500, TEM 750, GSl 65, GS2 65. L-AIa was also detected in positive ion mode, at fo 8.0, but with slightly different MS conditions. The retention times (tR, min; MRM ion pair, parent→product) of the authentic standards were as follows: L-AIa (8.0; 90→44), D- AIa (14.6). The MS parameters used were as follows: DP 21.0, EP 8.0, CE 15.0, CXP 5.0, CUR 50, CAD Medium, IS 4500, TEM 750, GSl 65, GS2 65. Asp was only detected weakly in positive ion mode and consequently negative ion mode was used with the same LC conditions. L-Asp eluted at tR 6.1 min, indicating that the configuration of the Asn unit was L. The retention times (tR, min; MRM ion pair, parent→product) of the authentic standards were as follows: L-Asp (6.1; 132→88), D- Asp (6.8). The MS parameters used were as follows: DP -30.0, EP -5.0, CE -18.5, CXP -13.0, CUR 30, CAD High, IS -4500, TEM 750, GSl 65, GS2 65.A sample of compound 3 was treated with 6 N HCl at 110 0C for 24 h. The hydrolysate was concentrated to dryness, reconstituted in 100 μL H2O and then analyzed by chiral HPLC [column, Chirobiotic TAG (4.6 x 250 mm), Supelco; solvent, MeOH-10 mM NH4OAc (40:60, pH 5.33): flow rate, 0.5 niL/min; detection by ESIMS in positive ion mode (MRM scan)]. N-Me-L-GIu, L-IIe, L- Leu, L-Pro and N-Me-D-Phe eluted at tR 6.0, 8.3, 8.6, 13.3 and 41.7 min, respectively. The retention times (tR, min; MRM ion pair, parent→product) of the authentic standards were as follows: N-Me-L-GIu (6.0; 162→44), N-Me-D-GIu (15.8), L-IIe (8.3; 132→86), L- α//o-Ile (8.5), D-α//o-Ile (19.6), D-IIe (22.2), L-Leu (8.6; 132→86), D-Leu (19.8), L- Pro (13.3; 116→70), D-Pro (35.2), N-Me-L-Phe (23.2; 180→134), and N-Me-D-Phe (41.7). To further separate the isobaric He and Leu units, different LC conditions were employed [column, Chirobiotic TAG (4.6 x 250 mm), Supelco; solvent, MeOH-10 mM NH4OAc (90:10, pH 5.65); flow rate, 0.5 niL/min; detection by MS (MRM scan)]. L-IIe and L-Leu eluted at tR 12.3 and 13.1 min, respectively. The retention times (tR, min; MRM ion pair, parent→product) of the authentic amino acid standards were as follows: L-IIe (12.3; 132→86), L-α//o-Ile (13.4), D-α//o-Ile (57.5), D-IIe (70.5), L-Leu (13.1; 132→86), and D-Leu (51.7). The MS parameters used were as follows: DP 31.0, EP 8.0, CE 17.3, CXP 3.1, CUR 35, CAD Medium, IS 4500, TEM 750, GSl 65, GS2 65.Hmpa in the hydrolysate of compound 3 was detected in negative ion mode [column, Chirobiotic TAG (4.6 x 250 mm), Supelco; solvent, MeOH-10 mM NH4OAc (40:60, pH 5.35); flow rate, 0.5 niL/min; detection by ESIMS in negative ion mode (MRM scan)]. The MS parameters used were as follows: DP -35.0, EP -8.0, CE -17.9, CXP -1.7, CUR 40, CAD Medium, IS -4500, TEM 750, GSl 65, GS2 65. (2^3S)-HmPa from the hydrolysate eluted at tR 6.4 min. The retention times (tR, min; MRM ion pair, parent→product) of the authentic standards were as follows: (2S,3R)-Hmpa (6.0; 131→85), (2S,3S)-Umpa (6.2; 131→85), (2R,3S)-Hmpa (6.4; 131→85), (2R,3R)-Hmpa (7.0; 131→85). The hydrolysate was examined under different HPLC conditions in order to confirm this assignment [column, Chiralpak MA (+) (4.6 x 50 mm), Daicel Chemical Industries, Ltd.; solvent, 2 mM CuSO4-CH3CN (85:15); flow rate, 1.0 niL/min; detection by UV absorption at 254 nm]. (2^3S)-HmPa from the hydrolysate eluted at tR 15.4 min. The retention times (tR, min) of the authentic standards were as follows: (2R5SS)-HmPa (15.4), (2R,3R)- Hmpa (17.9), (25,3R)-HmPa (22.7), (25,3S)-HmPa (27.5). Under these conditions, all other units eluted at tR <6.5 min.EXAMPLE 3BASE HYDROLYSIS TO DETERMINE CONFIGURATION OF HIVA UNITSThe acid hydrolysate of compound 1 was analyzed by chiral HPLC [column, Chirobiotic TAG (4.6 x 250 mm), Supelco; solvent, MeOH-10 mM NH4OAc (60:40, pH 5.63); flow rate, 0.5 niL/min; detection by ESIMS in negative ion mode (MRM scan)]. Both L-Hiva and D-Hiva were detected at tR 6.0 and 6.4 min, respectively. The retention times (tR, min; MRM ion pair, parent→product) of the authentic standards were as follows: L-Hiva (6.0; 117→71), D-Hiva (6.4). A sample of compound 1 (100 μg) was suspended in 80 μL MeOH-0.5 N NaOH (1:1) and left to stand at room temperature for 72 h. The solution was neutralized by the addition of 20 μL 1 N HCl, and was then analyzed by chiral HPLC-MS.Only L-Hiva was detected at tR 6.0 min. The retention times (tR, min; MRM ion pair, parent→product) of the authentic standards were as follows: L-Hiva (6.0; 117→71), D-Hiva (6.4). The MS parameters used were as follows: DP -30.0, EP -3.0, CE -17.3, CXP -2.0, CUR 45, CAD Medium, IS -4500, TEM 650, GSl 50, GS2 25.

Reference： [1]Current Patent Assignee: STATE UNIVERSITY SYSTEM OF FLORIDA - WO2010/151852, 2010, A2 Location in patent: Page/Page column 33-34

72
[ 17407-56-6 ]
[ 908093-98-1 ]
C₁₈H₂₀O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	In tetrahydrofuran at 20℃; for 2h;	65.1 Example 65 Synthesis of Compound (II-23) [Show Image] Step (1): Compound 23a + Compound 23b → Compound 23c; Compound 23a (4 g, 33.9 mmol) was dissolved in tetrahydrofuran (50 mL). While stirring, a tetrahydrofuran solution (30 mL) of diphenyldiazomethane 23b (6.91 g, 35.6 mmol) was added drop-wise thereto. After the reaction solution was stirred at room temperature for two hours, the solvent was evaporated under reduced pressure. n-Hexane (100 mL) was then added to the residue. The resulting solid was filtrated, and then washed with n-hexane to yield Compound 23c (8.25 g, 86%) as a solid. 1H-NMR (CDCl3) δ(delta): 7.36-7.29 (10H, m), 6.96 (1H, s), 4.16 (1H, d, J = 3.2 Hz), 2.67 (1H, br s), 2.23-2.13 (1H, m), 1.02 (3H, d, J = 7.0Hz), 0.77 (3H, d, J = 7.0 Hz).

Reference： [1]Current Patent Assignee: SHIONOGI & CO., LTD. - EP2341053, 2011, A1 Location in patent: Page/Page column 131-133

73
[ 17407-56-6 ]
[ 106-95-6 ]
(R)-allyl-2-hydroxy-3-methylbutanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl-formamide at 20℃;	Allyl (R)-2-hydroxy-3-methylbutanoate (13). To a solution of D-valic acid 33 (1.2 g, 10.2 mmol) andTBAI (0.75 g, 2.0 mmol) in dry DMF (25 mL) were added allyl bromide (1.8 mL, 20.3 mmol) and K2CO3(2.8 g, 20.3 mmol) at room temperature. After stirring overnight, the reaction mixture was quenched with 1N HCl and extracted with Et2O. The combined organic layer was washed with brine, driedover MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography(EtOAc/Hexane = 1:20) to give 1.5 g (93%) of ester 13 as a colorless oil. [α]D20 = +24.77 (c 1.00, CHCl3);1H-NMR (800 MHz, CDCl3) δ 5.84 (ddt, J = 17.1, 10.6, 5.9 Hz, 1H), 5.26 (dd, J = 17.2, 1.3 Hz, 1H), 5.18(dd, J = 10.4, 1.1 Hz, 1H), 4.61 (dd, J = 13.1, 5.9 Hz, 1H), 4.57 (dd, J = 13.2, 5.9 Hz, 1H), 3.98 (d, J = 3.9 Hz,1H), 2.87 (s, 1H), 2.01 (dtd, J = 13.9, 6.9, 3.7 Hz, 1H), 0.94 (d, J = 7.3 Hz, 3H), 0.79 (d, J = 7.2 Hz, 3H);13C-NMR (200 MHz, CDCl3) δ 174.4, 131.4, 118.9, 74.9, 65.8, 32.0, 18.6, 15.8; IR (thin film, neat) νmax3516, 2968, 1743, 1468, 1372, 1197, 1130, 933 cm-1; LR-MS (ESI+) m/z 181 (M + Na+); HR-MS (ESI+)calcd for C8H14NaO3 (M + Na+) 181.0835; found 181.0834.
	With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20℃; for 24h;

Reference： [1]Lim, Changjin [Molecules, 2019, vol. 24, # 19]
[2]Location in patent: experimental part Braunagel, Julia; Junghans, Ann; Koeper, Ingo [Australian Journal of Chemistry, 2011, vol. 64, # 1, p. 54 - 61]

74
[ 1342821-20-8 ]
[ 17407-56-6 ]
[ 2480-23-1 ]
[ 2566-30-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; water; at 110℃; for 15h;	Compound 1 (1.5 mg) was hydrolyzed with 6 M HCl (0.5 mL) at 110 C for 15 h. After concentration to dryness, the residue was dissolved in MeOH (200 muL) and subjected to HPLC analysis. In the same manner, compound 2 was hydrolyzed. HPLC analysis of the depsipeptide hydrolysates was performed using a ligand-exchange-type chiral column: Phenomenex Chirex 3126 (d)-penicillamine, 4.6×250 mm; mobile phase 2-propanol in 2 mM aqueous CuSO4; flow rate 1 mL/min, UV 235 nm. The 2-hydroxyisovaleric acid standard was purchased from Aldrich. Two mobile phase conditions were employed due to the large retention time differences of the standard samples: (1) 15% 2-propanol in 2 mM aqueous CuSO4, N-Me-l-Val and N-Me-d-Val (tR 7.0 min, peaks were superimposed), N-Me-l-Phe (tR 26.6 min), N-Me-d-Phe (tR 30.8 min), l-Hiv (tR 40.0 min), and d-Hiv (tR 67.4 min); (2) 5% 2-propanol in 2 mM aqueous CuSO4, N-Me-l-Val (tR 11.0 min), N-Me-d-Val (tR 13.9 min). Hydrolyzates of 1 and 2 contained N-Me-l-Val, N-Me-l-Phe, and d-Hiv.

Reference： [1]Tetrahedron,2011,vol. 67,p. 7929 - 7935

75
[ 1342821-22-0 ]
[ 17407-56-6 ]
[ 2480-23-1 ]
[ 2566-30-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; water; at 110℃; for 15h;	Compound 1 (1.5 mg) was hydrolyzed with 6 M HCl (0.5 mL) at 110 C for 15 h. After concentration to dryness, the residue was dissolved in MeOH (200 muL) and subjected to HPLC analysis. In the same manner, compound 2 was hydrolyzed. HPLC analysis of the depsipeptide hydrolysates was performed using a ligand-exchange-type chiral column: Phenomenex Chirex 3126 (d)-penicillamine, 4.6×250 mm; mobile phase 2-propanol in 2 mM aqueous CuSO4; flow rate 1 mL/min, UV 235 nm. The 2-hydroxyisovaleric acid standard was purchased from Aldrich. Two mobile phase conditions were employed due to the large retention time differences of the standard samples: (1) 15% 2-propanol in 2 mM aqueous CuSO4, N-Me-l-Val and N-Me-d-Val (tR 7.0 min, peaks were superimposed), N-Me-l-Phe (tR 26.6 min), N-Me-d-Phe (tR 30.8 min), l-Hiv (tR 40.0 min), and d-Hiv (tR 67.4 min); (2) 5% 2-propanol in 2 mM aqueous CuSO4, N-Me-l-Val (tR 11.0 min), N-Me-d-Val (tR 13.9 min). Hydrolyzates of 1 and 2 contained N-Me-l-Val, N-Me-l-Phe, and d-Hiv.

Reference： [1]Tetrahedron,2011,vol. 67,p. 7929 - 7935

76
[ 1342309-23-2 ]
[ 17407-56-6 ]
[ 17407-55-5 ]
[ 312-84-5 ]
[ 56-45-1 ]
[ 20312-37-2 ]
[ 13748-90-8 ]
[ 3060-46-6 ]
[ 63-91-2 ]
[ 31321-74-1 ]
[ 673-06-3 ]

Reference： [1]Journal of Natural Products,2011,vol. 74,p. 2137 - 2142

77
[ 1342309-24-3 ]
[ 17407-56-6 ]
[ 17407-55-5 ]
[ 312-84-5 ]
[ 56-45-1 ]
[ 20312-37-2 ]
[ 13748-90-8 ]
[ 3060-46-6 ]
[ 63-91-2 ]
[ 31321-74-1 ]
[ 673-06-3 ]

Reference： [1]Journal of Natural Products,2011,vol. 74,p. 2137 - 2142

78
[ 17407-56-6 ]
[ 18162-48-6 ]
[ 119619-47-5 ]

Yield	Reaction Conditions	Operation in experiment
57%	Stage #1: (R)-2-Hydroxy-3-methylbutyric acid; tert-butyldimethylsilyl chloride With 1H-imidazole In N,N-dimethyl-formamide for 24h; Stage #2: With water; potassium carbonate In methanol at 0 - 20℃; for 2.5h;	3 (R)-TBS-Protected Alcohol 972b (R)-TBS-Protected Alcohol 972b: (0151) The compound was prepared according to J. Chem. Soc., Perkin Trans. 1, 1996, 1427-1433 while the analytics are compared to Analytics compared to: J. Org. Chem. 1989, 54, 2085-2091. (R)-2-Hydroxy-3-methylbutyric acid (not shown) (305 mg, 2.58 mmol, 1.00 eq.), TBS-Cl (934 mg, 6.20 mmol, 2.40 eq.) and imidazole (1.07 g, 12.4 mmol, 4.80 eq) were dissolved in 3.5 mL DMF at RT. The mixture was stirred 24 h. The mixture was diluted with 65 mL EtOAc, washed 3× with 10 mL sat. aq. citric acid, sat. aq. NaHCO3 and brine, dried over MgSO4 and concentrated. The resulting oil was dissolved in 22 mL MeOH and cooled to 0° C. 650 mg K2CO3 in 8 mL H2O were added and the mixture was stirred for 2.5 h at RT. The solution was adjusted to pH 4 (aq. HC 1 M) and the aq. phase was extracted with EtOAc (3×40 mL). The combined org. phase was dried over MgSO4 and concentrated. The colorless oil was purified by FC (hexane/EtOAc 6:1→4:1) to deliver (R)-TBS-protected alcohol 972b (339 mg, 57% over 2 steps) as a colorless oil. (0152) Rf: 0.25 (10% MeOH in CH2Cl2) (0153) [α]2D: +18.31 (c 0.942, CH2Cl2) (0154) 1H-NMR: (400 MHz, CDCl3) δ 4.05 (d, J=4.0 Hz, 1H), 2.16-2.01 (m, 1H), 0.97 (d, J=6.9 Hz, 3H), 0.95-0.91 (m, 12H), 0.09 (s, 6H). (0155) 13C-NMR: (101 MHz, CDCl3) δ 176.9, 76.7, 32.8, 25.7, 18.8, 16.7, -5.2. (0156) HR-MS: (ESI): m/z calc. for C11H23O3 Si [M-H]- 231.1422. found 231.1424.
339 mg	Stage #1: (R)-2-Hydroxy-3-methylbutyric acid; tert-butyldimethylsilyl chloride With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere; Schlenk technique; Stage #2: With potassium carbonate In methanol; water at 0 - 20℃; for 2.5h;

Reference： [1]Current Patent Assignee: EIDGENÖSSISCHE TECHNISCHE HOCHSCHULE ZÜRICH - US2015/246907, 2015, A1 Location in patent: Paragraph 0150-0156
[2]Horlacher, Oliver P.; Hartkoorn, Ruben C.; Cole, Stewart T.; Altmann, Karl-Heinz [ACS Medicinal Chemistry Letters, 2013, vol. 4, # 2, p. 264 - 268]

79
[ 17407-56-6 ]
[ 222714-37-6 ]
[ 1622141-94-9 ]

Yield	Reaction Conditions	Operation in experiment
75%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃;	2.1.B PREPARATION 2 Synthesis of methyl 4-[(1S)-1-[[(2R)-2-hydroxy-3-methyl-butanoyl]amino]ethyl]benzoate Scheme 1, Step B. A mixture of 4-[(1S)-1-aminoethyl]-benzoic acid, methyl ester (5.8 g; 49.1 mmol), (2R)-2-hydroxy-3-methyl-butanoic acid (9.3 g; 51.9 mmol), 1-hydroxybenzotriazole (0.82 g; 6.1 mmol), and triethylamine (22 mL; 158 mmol) in CH2Cl2 (120 mL) is treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (14.2 g; 74.1 mmol). The cloudy mixture is stirred at room temperature overnight. The reaction mixture is washed with 1N HCl (2*150 mL) then brine. The organic layer is dried over MgSO4, filtered, concentrated, and dried under high vacuum to provide the title compound as a white solid (10.24 g, 75%). This material is used in the next step without further purification. MS (m/z): 280.0 (M+1). 1H NMR (400 MHz, DMSO-d6): δ 8.14-8.12 (m, 1H), 7.87-7.84 (m, 2H), 7.45-7.43 (m, 2H), 5.35 (d, J=5.7 Hz, 1H), 5.00-4.95 (m, 1H), 3.79 (s, 3H), 3.64 (dd, J=4.0, 5.7 Hz, 1H), 1.93-1.89 (m, 1H), 1.36 (d, J=7.2 Hz, 3H), 0.81 (d, J=6.9 Hz, 3H), 0.65 (d, J=6.7 Hz, 3H).
54%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; ethyl cyanoglyoxylate-2-oxime In N,N-dimethyl-formamide at 27℃; for 18h; Cooling with ice;	Step (i) To an ice-cooled solution of (2R)-2-hydroxy-3-methyl-butanoic acid (10.0 g, 84.7 mmol) and methyl (S)-4-(1-aminoethyl)benzoate (16.7 g, 93.1 mmol) in DMF (170 mL) was added EDC HCI (24.3 g, 127.0 mmol), ethyl (hydroxyimino)cyanoacetate (13.2 g, 93.1 mmol) and triethylamine (29.5 mL, 211.6 mmol). The mixture was stirred at RT for 18 hrs after which it was partitioned between EtOAc and water. The organics were separated, washed sequentially with 1 M HCI, sat. aq. NaHCO3 and brine, dried over MgSO4 and concentrated to afford Intermediate 1 , methyl 4-((S)-1-((R)-2-hydroxy-3-methylbutanamido)ethyl)benzoate (12.8 g, 45.9 mmol, 54% yield) as an orange solid. Data available in Table 3

Reference： [1]Current Patent Assignee: ELI LILLY & CO - US2014/235718, 2014, A1 Location in patent: Paragraph 0029-0032
[2]Current Patent Assignee: SOSEI GROUP CORPORATION - WO2021/69927, 2021, A1 Location in patent: Page/Page column 42; 61-62

80
(3S, 6R)-4-methyl-6-(1-methylethyl)-3-phenylmethylperhydro-1,4-oxazine-2,5-dione [ No CAS ]
[ 17407-56-6 ]
[ 2566-30-5 ]

Yield	Reaction Conditions	Operation in experiment
5 mg; 4.3 mg	With hydrogenchloride; In water; at 110℃; for 24h;Sealed tube; Inert atmosphere;	10 mg of 1bwas treated with 15 mL of 6 N HCl (pa) and heated at 110 C for 24 hin ampoules previously sealed under N2 gas. The resulting solutionwas added to 15 mL of H2O and then extracted three times with 15 mLdiethylether to obtain 5 mg of 2-hydroxy-3-methylbutyric acid. The aqueoussolution was then evaporated under vacuum to afford 4.3 mg of N-methylphenylalanine.2-Hydroxy-3-methylbutyricacid was then analyzed with GC-MS and further investigatedfor its absolute configuration by examination of its specific optical rotationvalue and menthyl ester derivatization.Moreover, the absolute configuration of N-methylphenylalanine was alsoanalyzed by examination of its specific optical rotation value and Marfeyderivatization.

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 6184 - 6187

81
[ 17407-56-6 ]
[ 74-88-4 ]
[ 90244-32-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;

Reference： [1]Kang, Chang Won; Ranatunga, Sujeewa; Sarnowski, Matthew P.; Del Valle, Juan R. [Organic Letters, 2014, vol. 16, # 20, p. 5434 - 5437]

82
[ 17407-56-6 ]
5-piperazin-1-ylmethyl-thiophene-2-carboxylic acid (2-methoxypyridin-4-ylmethyl)amide hydrochloride [ No CAS ]
5-[4-((R)-2-hydroxy-3-methylbutyryl)piperazin-1-ylmethyl]thiophene-2-carboxylic acid (2-methoxypyridin-4-ylmethyl)amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With 4-methyl-morpholine; dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 40℃;	30 Example 30: 5-[4-((R)-2-Hydroxy-3-methyl-butyryl)-piperazin-1-ylmethyl]-thiophene-2-carboxylic acid (2-methoxy-pyridin-4-ylmethyl)-amide To (R)-(+)-2-Hydroxy-3-methylbuttyric acid (15 mg, 0.13 mmol), a solution containing HOBt*H2O (0.13 mmol), N-methylmorpholine and 0.01 mmol DMAP in 0.75 ml DMF was added and the mixture was stirred at RT until the acid had dissolved. Then 5-piperazin-1-ylmethyl-thiophene-2-carboxylic acid (2-methoxy-pyridin-4-ylmethyl)-amide (Intermediate 5) (42 mg, 0.11 mmol) in 1 ml DMF was added, followed by 0.13 mmol EDC (neat). The tube was closed with a screw cap and shaken over night at 40 °C. 0.1 ml TFA was added and the volume was adjusted to 2.2 ml with DMF. The solution was filtered and submitted to SFC purification to give the title compound as a colorless film (17 mg, 30%). 1 H NMR (DMSO-d6, 500 MHz) δ ppm 9.02 (t, 1 H), 8.1 (d, 1 H), 7.66 (d, 1 H), 7.02 (d, 1 H), 6.90 (d, 1 H), 6.68 (s, 1 H), 4.6 (bs, 1 H), 4.41 (d, 2H), 4.03 (d, 1 H), 3.82 (s, 3H), 3.7 (s, 2H), 3.6-3.4 (m, 4H), 2.45-2.3 (m, 4H), 1.89 (m, 1 H), 0.88 (d, 3H), 0.78 (d, 3H). LC/MS (Method 3); Rt = 1.26 min; detected mass: m/z = 447.20 ([M+H]+).

Reference： [1]Current Patent Assignee: SANOFI - EP2881390, 2015, A1 Location in patent: Paragraph 0080

83
[ 17407-56-6 ]
5-piperazin-1-ylmethyl-thiophene-2-carboxylic acid (2-methoxy-pyridin-ylmethyl)amide hydrochloride [ No CAS ]
5-[4-((R)-2-hydroxy-3-methyl-butyryl)-piperazin-1-ylmethyl]-thiophene-2-carboxylic acid (2-methoxy-pyridin-4-ylmethyl)-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	Stage #1: (R)-2-Hydroxy-3-methylbutyric acid With 4-methyl-morpholine; dmap; benzotriazol-1-ol In N,N-dimethyl-formamide at 20 - 25℃; Stage #2: 5-piperazin-1-ylmethyl-thiophene-2-carboxylic acid (2-methoxy-pyridin-ylmethyl)amide hydrochloride With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 40℃; Sealed tube;	30 Example 30: 5-[4-((R)-2-Hydroxy-3-methyl-butyryl)-piperazin-1 -ylmethyl]-thiophene-2- carboxylic acid (2-methoxy-pyridin-4-ylmethyl)-amide Example 30: 5-[4-((R)-2-Hydroxy-3-methyl-butyryl)-piperazin-1 -ylmethyl]-thiophene-2- carboxylic acid (2-methoxy-pyridin-4-ylmethyl)-amide To (R)-(+)-2-Hydroxy-3-methylbuttyric acid (15 mg, 0.13 mmol), a solution containing HOBt*H2O (0.13 mmol), N-methylmorpholine and 0.01 mmol DMAP in 0.75 ml DMF was added and the mixture was stirred at RT until the acid had dissolved. Then 5- piperazin-1 -ylmethyl-thiophene-2-carboxylic acid (2-methoxy-pyridin-4-ylmethyl)-amide (Intermediate 5) (42 mg, 0.1 1 mmol) in 1 ml DMF was added, followed by 0.13 mmol EDC (neat). The tube was closed with a screw cap and shaken over night at 40 °C. 0.1 ml TFA was added and the volume was adjusted to 2.2 ml with DMF. The solution was filtered and submitted to SFC purification to give the title compound as a colorless film (17 mg, 30%). 1 H NMR (DMSO-d6, 500 MHz) δ ppm 9.02 (t, 1 H), 8.1 (d, 1 H), 7.66 (d, 1 H), 7.02 (d, 1 H), 6.90 (d, 1 H), 6.68 (s, 1 H), 4.6 (bs, 1 H), 4.41 (d, 2H), 4.03 (d, 1 H), 3.82 (s, 3H), 3.7 (s, 2H), 3.6-3.4 (m, 4H), 2.45-2.3 (m, 4H), 1 .89 (m, 1 H), 0.88 (d, 3H), 0.78 (d, 3H). LC/MS ( Method 3); Rt = 1 .26 min; detected mass: m/z = 447.20 ([M+H]+).

Reference： [1]Current Patent Assignee: SANOFI - WO2015/82474, 2015, A1 Location in patent: Page/Page column 48

84
[ 17407-56-6 ]
[ 26048-05-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1.1: caesium carbonate / N,N-dimethyl-formamide / 0.67 h / 0 °C / Inert atmosphere 1.2: 15 h / 0 - 20 °C / Inert atmosphere 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere 3.1: hydrogenchloride / 1,4-dioxane / 3 h / 20 °C / Inert atmosphere 4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 17 h / 0 - 20 °C / Inert atmosphere 5.1: hydrogenchloride / 1,4-dioxane / 6 h / 20 °C / Inert atmosphere 6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere 7.1: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere 8.1: hydrogenchloride / 1,4-dioxane / 6 h / 20 °C / Inert atmosphere 9.1: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 10.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18.5 h / 0 - 20 °C / Inert atmosphere
	Multi-step reaction with 11 steps 1.1: caesium carbonate / N,N-dimethyl-formamide / 0.67 h / 0 °C / Inert atmosphere 1.2: 15 h / 0 - 20 °C / Inert atmosphere 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere 3.1: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere 4.1: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.33 h / 0 °C / Inert atmosphere 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 17 h / 0 - 20 °C / Inert atmosphere 6.1: hydrogenchloride / 1,4-dioxane / 6 h / 20 °C / Inert atmosphere 7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere 8.1: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere 9.1: hydrogenchloride / 1,4-dioxane / 6 h / 20 °C / Inert atmosphere 10.1: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18.5 h / 0 - 20 °C / Inert atmosphere
	Multi-step reaction with 9 steps 1.1: caesium carbonate / N,N-dimethyl-formamide / 0.67 h / 0 °C / Inert atmosphere 1.2: 15 h / 0 - 20 °C / Inert atmosphere 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere 3.1: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere 4.1: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.33 h / 0 °C / Inert atmosphere 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere 6.1: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere 7.1: hydrogenchloride / 1,4-dioxane / 6 h / 20 °C / Inert atmosphere 8.1: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 9.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18.5 h / 0 - 20 °C / Inert atmosphere

Reference： [1]Lücke, Daniel; Dalton, Toryn; Ley, Steven V.; Wilson, Zoe E. [Chemistry - A European Journal, 2016, vol. 22, # 12, p. 4206 - 4217]
[2]Lücke, Daniel; Dalton, Toryn; Ley, Steven V.; Wilson, Zoe E. [Chemistry - A European Journal, 2016, vol. 22, # 12, p. 4206 - 4217]
[3]Lücke, Daniel; Dalton, Toryn; Ley, Steven V.; Wilson, Zoe E. [Chemistry - A European Journal, 2016, vol. 22, # 12, p. 4206 - 4217]

85
[ 17407-56-6 ]
[ 2052-49-5 ]
C₁₆H₃₆N⁽¹⁺⁾*C₅H₉O₃^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol at 20℃; for 2h; Inert atmosphere;	Tetrabutylammonium salts General procedure: The tetrabutylammonium salts were prepared by adding 1 equiv tetrabutylammonium hydroxide in methanol to a solution of corresponding carboxylic acid (1 equiv) in methanol [21]. The mixture was stirred at room temperature for 2 h and evaporated to dryness under reduced pressure. The resulting syrup was dried at high vacuum for 24 h, stored in the desiccators.

Reference： [1]Bozkurt, Selahattin; Turkmen, Mustafa Burak; Soykan, Cengiz [Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2016, vol. 84, # 1-2, p. 35 - 41]

86
urumamide [ No CAS ]
[ 3913-67-5 ]
[ 72-18-4 ]
[ 17407-56-6 ]
[ 2480-23-1 ]
[ 61-90-5 ]
[ 3060-46-6 ]
[ 4125-98-8 ]
[ 147-85-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In water; at 110℃; for 24h;	Urumamide (1) (0.7 mg) was treated with 9 N HCl (100 L) for 24 h at 110 C. The hydrolyzed product was evaporated to dryness and could be separated into each component by HPLC. [Cosmosil 5C18-PAQ (4.6 × 250 mm); flowrate, 1.0 mL/min; detection at 215 nm; solvent H2O. Retention times (min) of components: N-Me-Ala (tR = 3.0 min), Pro(tR = 3.2 min), Val (tR = 3.4 min), N-Me-Val (tR = 3.7 min), Leu (tR = 4.8 min), N-Me-Ile (tR = 5.3 min), N-Me-Leu (tR =6.0 min)].

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 4213 - 4216

87
[ 17407-56-6 ]
6-(1-(1-(2-methoxyethyl)piperidin-4-yl)-1H-pyrazol-4-yl)-4-(6-(piperazin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carbonitrile dihydrochloride [ No CAS ]
(R)-4-(6-(4-(2-hydroxy-3-methylbutanoyl)piperazin-1-yl)pyridin-3-yl)-6-(1-(1-(2-methoxyethyl)piperidin-4-yl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;	715.5 Step 5: Preparation of (R)-4-(6-(4-(2-hydroxy-3 -methylbutanoyl)piperazin- 1- yl)pyridin-3 -yl)-6-(1-(1-(2-methoxyethyl)piperidin-4-yl)-1H-pyrazol-4-yl)pyrazolo[1.5-alpyridine-3 -carbonitrile. A solution of 6-( 1 -(1 -(2-methoxyethyl)piperidin-4-yl)- 1H-pyrazol-4-yl)-4-(6-(piperazin- 1 -yl)pyridin-3 -yl)pyrazolo[ 1,5 -a]pyridine-3 -carbonitrile dihydrochloride (31mg, 0.053 mmol) in DMF (1.1 mL) was treated with D-alpha-Hydroxyisovaleric acid (7.5 mg, 0.064 mmol), HATU (24.2 mg, 0.0636 mmol) and DIEA (46.2 tL, 0.265 mmol). The resulting solution was stirred overnight at ambient temperature. The reaction mixture was diluted with 5% MeOHIDCM (20 mL) and washed with water (5 mL). The combined organic extracts were dried over anhydrous MgSO4, then filtered and concentrated in vacuo. The crude residue was purified by silica chromatography (8% MeOHIDCM with 2% NH4OH(aq) as the eluent) to cleanly afford the title compound (20 mg, 62% yield). MS (apci) m/z = 611.9, 612.9 (M+1).

Reference： [1]Current Patent Assignee: PFIZER INC - WO2017/11776, 2017, A1 Location in patent: Paragraph 001858

88
[ 17407-56-6 ]
6-(2-methylthiazol-5-yl)-4-(6-(piperazin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carbonitrile dihydrochloride [ No CAS ]
(R)-4-(6-(4-(2-hydroxy-3-methylbutanoyl)piperazin-1-yl)pyridin-3-yl)-6-(2-methylthiazol-5-yl)pyrazolo[1,5-a]pyridine-3-carbonitrile 2,2,2-trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃;	723.3 Step 3: Preparation of (R)-4-(6-(4-(2-hydroxy-3 -methylbutanoyl)piperazin- 1- yl)pyridin-3 -yl)-6-(2-methylthiazol-5-yl)pyrazolo[ 1 ,5-alpyridine-3-carbonitrile 2,2,2- trifluoroacetate. A solution of 6-(2-methylthiazol-5 -yl)-4-(6-(piperazin- 1 -yl)pyridin-3 -yl)pyrazolo[1,5-a]pyridine-3-carbonitrile dihydrochloride (42 mg, 0.0885 mmol) in DCM (3 mL)was treated with DIEA (61.7 tL, 0. 354 mmol), D-alpha-Hydroxyisovaleric acid (12.5 mg, 0.106mmol) and HATU (40.4 mg, 0.106 mmol). The resulting solution was stirred overnight at ambienttemperature. The reaction mixture was concentrated in vacuo, and the crude residue was purifiedby C18 reverse-phase chromatography (5-95% ACN/water with 0.1% TFA as the gradient eluent)to cleanly afford the title compound as the bistrifluoroacetate salt (15 mg, 28% yield). MS (apci)m/z = 502.2 (M+H).

Reference： [1]Current Patent Assignee: PFIZER INC - WO2017/11776, 2017, A1 Location in patent: Paragraph 001884

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	17407-56-6	MDL No. :	MFCD00066442
Formula :	C₅H₁₀O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NGEWQZIDQIYUNV-SCSAIBSYSA-N
M.W :	118.13	Pubchem ID :	5289545
Synonyms :

Num. heavy atoms :	8
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.8
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	29.08
TPSA :	57.53 Å²

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.67 cm/s

Log Po/w (iLOGP) :	0.93
Log Po/w (XLOGP3) :	0.5
Log Po/w (WLOGP) :	0.09
Log Po/w (MLOGP) :	0.01
Log Po/w (SILICOS-IT) :	-0.3
Consensus Log Po/w :	0.25

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[ 17407-56-6 ] Synthesis Path-Downstream 1~88

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[ 17407-56-6 ]

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Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Log S (ESOL) :	-0.76
Solubility :	20.7 mg/ml ; 0.176 mol/l
Class :	Very soluble
Log S (Ali) :	-1.28
Solubility :	6.23 mg/ml ; 0.0527 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	0.5
Solubility :	374.0 mg/ml ; 3.17 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.46

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

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P378
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
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P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
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P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
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P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
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P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
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P411 + P235	Keep cool.
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[ CAS No. 17407-56-6 ] {[proInfo.proName]}

Quality Control of [ 17407-56-6 ]

Related Doc. of [ 17407-56-6 ]

Product Details of [ 17407-56-6 ]

Calculated chemistry of [ 17407-56-6 ]

Physicochemical Properties

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Druglikeness

Water Solubility

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Safety of [ 17407-56-6 ]

Application In Synthesis of [ 17407-56-6 ]

[ 17407-56-6 ] Synthesis Path-Upstream 1~2

[ 17407-56-6 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 17407-56-6 ]

Aliphatic Chain Hydrocarbons

Alcohols

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 17407-56-6 ]