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[ CAS No. 1509-35-9 ] {[proInfo.proName]}

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Chemical Structure| 1509-35-9
Chemical Structure| 1509-35-9
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Product Details of [ 1509-35-9 ]

CAS No. :1509-35-9 MDL No. :MFCD00066445
Formula : C6H13NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :AGPKZVBTJJNPAG-CRCLSJGQSA-N
M.W : 131.17 Pubchem ID :94206
Synonyms :

Calculated chemistry of [ 1509-35-9 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.83
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 35.44
TPSA : 63.32 Ų

Pharmacokinetics

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) : -8.32 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.26
Log Po/w (XLOGP3) : -1.72
Log Po/w (WLOGP) : 0.44
Log Po/w (MLOGP) : -1.82
Log Po/w (SILICOS-IT) : -0.15
Consensus Log Po/w : -0.4

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 0.63
Solubility : 557.0 mg/ml ; 4.25 mol/l
Class : Highly soluble
Log S (Ali) : 0.9
Solubility : 1050.0 mg/ml ; 8.02 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -0.14
Solubility : 96.1 mg/ml ; 0.733 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.65

Safety of [ 1509-35-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1509-35-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1509-35-9 ]

[ 1509-35-9 ] Synthesis Path-Downstream   1~84

  • 1
  • [ 1509-35-9 ]
  • (2R,3S)-2-hydroxy-3-methylpentanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With sulfuric acid; sodium nitrite In water at 5 - 20℃; for 4h;
69% With sulfuric acid; sodium nitrite at 0℃; for 6h; Inert atmosphere;
With hydrogenchloride; acetic acid; sodium nitrite
With hydrogenchloride; acetic acid; sodium nitrite
With hydrogenchloride; water; acetic acid; sodium nitrite 1.) 0 deg C, 20 min, 2.) RT, 15 h; Yield given. Multistep reaction;
With sulfuric acid; water; sodium nitrite for 13h;
With perchloric acid; sodium nitrite In water at 0℃; Heating;
15.6 mg With perchloric acid; sodium nitrite In water at 0℃; Reflux;
With perchloric acid; water; sodium sulfite at 0 - 100℃;
Stage #1: D-alloisoleucine With perchloric acid; sodium nitrite In water at 0 - 20℃; for 1h; Stage #2: In water for 0.05h; Reflux;
With perchloric acid; water; sodium nitrite at 0℃; Reflux;
With perchloric acid; sodium nitrite In water at 0 - 20℃; for 0.5h; 4.6. Preparation of isomers of 2-hydroxyisoleucic acid (Hila) General procedure: L-Isoleucine (100 mg, 0.75 mmol) was dissolved in 50 mL of 0.2 N perchloric acid (0 °C). To this was added a cold (0 °C) solution of NaNO2 (1.4 g, 20 mmol) in 20 mL of H2O with rapid stirring. With continued stirring the reaction mixture was allowed to reach r.t. until evolution of N2 subsided (about 30 min). The solution was then brought to boil for 3 min, cooled to r.t., and saturated with NaCl. The mixture was then extracted with Et2O and dried under vacuum to give 2S, 3S-Hila (L-Hila). The three other stereoisomers 2R,3R-Hila (D-Hila), 2R, 3S-Hila (D-allo-Hila), and 2S, 3R-Hila (L-allo- Hila) were synthesized in a similar manner from D-Ile, D-allo-Ile, and L-allo-Ile, respectively (Mamer, 2000; Mamer and Reimer, 1992).
With sulfuric acid; sodium nitrite In water 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; sodium nitrite at 0 - 20℃; for 17h;
With sulfuric acid; sodium nitrite In water at 5℃;
With perchloric acid; sodium nitrite at 0 - 20℃; for 0.05h; 3.5. Preparation of 2-Hydroxy-3-methylpentanoic Acid (Hmpa) General procedure: To a stirring solution of L-Ile (10 mg, 0.076 mmol) in 0.2 M perchloric acid (5 mL) was added acold (0 °C) solution of 1 M NaNO2 (2 mL) at 0 °C. With continued rapid stirring, the reaction mixturewas allowed to reach room temperature until evolution of N2 subsided (about 30 min). The solutionwas then boiled for 3 min, cooled to room temperature, and saturated with NaCl before extraction withEt2O and drying under vacuum to give (2S,3S)-Hmpa (L-Hmpa). The three other stereoisomers(2S,3R)-Hmpa (L-allo-Hmpa), (2R,3R)-Hmpa (D-Hmpa), and (2R,3S)-Hmpa (D-allo-Hmpa) weresynthesized in a similar manner from L-allo-Ile, D-Ile, and D-allo-Ile, respectively.
With sulfuric acid; sodium nitrite In water at 0℃; for 6h; Allyl (2R,3S)-2-hydroxy-3-methylpentanoate (12). To a solution of D-allo-Ile 31 (1.4 g, 10.7 mmol) indilute sulfuric acid (0.8N in H2O, 26.7 mL, 21.3 mmol) was added NaNO2 (2.2 g, 32.0 mmol) slowly at 0°C. After stirring for 6 h at the same temperature, the reaction mixture was diluted with Et2O andextracted with Et2O. The combined organic layer was dried over MgSO4 and concentrated in vacuo.The residue was used in the next step without further purification. To a solution of crude acid 32(10.7 mmol) and TBAI (0.79 g, 2.13 mmol) in dry DMF (500 mL) were added allyl bromide (1.8 mL,21.3 mmol) and K2CO3 (3.0 g, 21.3 mmol) at room temperature. After stirring for overnight, the reactionmixture was quenched with 1N HCl and extracted with Et2O. The combined organic layer was washedwith brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash columnchromatography (EtOAc/Hexane = 1:10) to give 1.2 g (65% for 2 steps) of ester 12 as a colorless oil.[α]D20 = +45.94 (c 0.50, CHCl3); 1H-NMR (800 MHz, CDCl3) δ5.89 (ddt, J = 17.1, 10.5, 5.9 Hz, 1H), 5.31(ddd, J = 17.2, 2.9, 1.5 Hz, 1H), 5.24 (dd, J = 10.4, 2.3, 1.2 Hz, 1H), 4.67 (ddt, J = 13.0, 5.9, 1.2 Hz, 1H),4.63 (ddt, J = 13.1, 5.9, 1.3 Hz, 1H), 4.17 (d, J = 3.0 Hz, 1H), 2.61 (s, 1H), 1.83-1.75 (m, 1H), 1.50 (ddq,J = 13.8, 7.4, 7.2 Hz, 1H), 1.28 (ddq, J = 13.7, 7.5, 7.4 Hz, 1H), 0.91 (t, J = 7.5 Hz, 3H), 0.78 (d, J = 7.0 Hz,3H); 13C-NMR (200 MHz, CDCl3) δ 175.0, 131.5, 119.1, 72.9, 66.0, 38.5, 25.9, 13.1, 11.8; IR (thin film,neat) νmax 3524, 2966, 1742, 1461, 1384, 1200, 1138, 934 cm1; LR-MS (ESI+) m/z 173 (M + H+); HR-MS(ESI+) calcd for C29H45N4O7 (M + H+) 173.1172; found 173.1163.-
With sulfuric acid; sodium nitrite In water at 0 - 20℃; for 19.25h; Inert atmosphere; Schlenk technique;
Stage #1: D-alloisoleucine With sulfuric acid at 0℃; for 0.25h; Stage #2: With sodium nitrite at 0 - 20℃; for 18h;

Reference: [1]Location in patent: experimental part Pettit, George R.; Hu, Shougang; Knight, John C.; Chapuis, Jean-Charles [Journal of Natural Products, 2009, vol. 72, # 3, p. 372 - 379]
[2]Dai, Lu; Chen, Bo; Lei, Honghui; Wang, Zhuo; Liu, Yuqing; Xu, Zhengshuang; Ye, Tao [Chemical Communications, 2012, vol. 48, # 69, p. 8697 - 8699]
[3]Winitz et al. [Journal of the American Chemical Society, 1956, vol. 78, p. 2423,2428]
[4]Kallmerten, James; Gould, Thomas J. [Journal of Organic Chemistry, 1986, vol. 51, # 7, p. 1152 - 1155]
[5]Kurome, Toru; Inami, Kaoru; Inoue, Tetsuya; Ikai, Katsushige; Takesako, Kazutoh; Kato, Ikunoshin; Shiba, Tetsuo [Tetrahedron, 1996, vol. 52, # 12, p. 4327 - 4346]
[6]Ikeda, Yoshitaka; Nonaka, Hikaru; Furumai, Tamotsu; Igarashi, Yasuhiro [Journal of Natural Products, 2005, vol. 68, # 4, p. 572 - 573]
[7]Location in patent: experimental part Simmons, T. Luke; Engene, Niclas; Urena, Luis David; Romero, Luz I.; Ortega-Barria, Eduardo; Gerwick, Lena; Gerwick, William H. [Journal of Natural Products, 2008, vol. 71, # 9, p. 1544 - 1550]
[8]Location in patent: experimental part Choi, Hyukjae; Pereira, Alban R.; Cao, Zhengyu; Shuman, Cynthia F.; Engene, Niclas; Byrum, Tara; Matainaho, Teatulohi; Murray, Thomas F.; Mangoni, Alfonso; Gerwick, William H. [Journal of Natural Products, 2010, vol. 73, # 8, p. 1411 - 1421]
[9]Tripathi, Ashootosh; Puddick, Jonathan; Prinsep, Michele R.; Rottmann, Matthias; Tan, Lik Tong [Journal of Natural Products, 2010, vol. 73, # 11, p. 1810 - 1814]
[10]Location in patent: experimental part Mevers, Emily; Liu, Wei-Ting; Engene, Niclas; Mohimani, Hosein; Byrum, Tara; Pevzner, Pavel A.; Dorrestein, Pieter C.; Spadafora, Carmenza; Gerwick, William H. [Journal of Natural Products, 2011, vol. 74, # 5, p. 928 - 936]
[11]Location in patent: experimental part Simmons, T. Luke; Nogle, Lisa M.; Media, Joseph; Valeriote, Frederick A.; Mooberry, Susan L.; Gerwick, William H. [Journal of Natural Products, 2009, vol. 72, # 6, p. 1011 - 1016] Location in patent: experimental part Thornburg, Christopher C.; Thimmaiah, Muralidhara; Shaala, Lamiaa A.; Hau, Andrew M.; Malmo, Jay M.; Ishmael, Jane E.; Youssef, Diaa T. A.; McPhail, Kerry L. [Journal of Natural Products, 2011, vol. 74, # 8, p. 1677 - 1685]
[12]Location in patent: experimental part Tripathi, Ashootosh; Puddick, Jonathan; Prinsep, Michele R.; Rottmann, Matthias; Chan, Kok Ping; Chen, David Yu-Kai; Tan, Lik Tong [Phytochemistry, 2011, vol. 72, # 18, p. 2369 - 2375]
[13]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]
[14]Tan, Karen Co; Wakimoto, Toshiyuki; Abe, Ikuro [Organic Letters, 2014, vol. 16, # 12, p. 3256 - 3259]
[15]Jamison, Matthew T.; Molinski, Tadeusz F. [Journal of Natural Products, 2016, vol. 79, # 9, p. 2243 - 2249]
[16]Luo, Danmeng; Putra, Masteria Y.; Ye, Tao; Paul, Valerie J.; Luesch, Hendrik [Marine Drugs, 2019, vol. 17, # 2]
[17]Lim, Changjin [Molecules, 2019, vol. 24, # 19]
[18]Kienle, Maryline; Eisenring, Patrick; Stoessel, Barbara; Horlacher, Oliver P.; Hasler, Samuel; Van Colen, Gwénaëlle; Hartkoorn, Ruben C.; Vocat, Anthony; Cole, Stewart T.; Altmann, Karl-Heinz [Journal of Medicinal Chemistry, 2020, vol. 63, # 3, p. 1105 - 1131]
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  • 3
  • [ 1509-35-9 ]
  • [ 108-24-7 ]
  • [ 64-19-7 ]
  • (2S,3S)-N-acetyl-2-amino-3-methylpentanoic acid [ No CAS ]
  • [ 54831-20-8 ]
  • 4
  • [ 62210-73-5 ]
  • [ 1509-35-9 ]
  • N-benzyloxycarbonylamino-D-alloisoleucine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In tetrahydrofuran; water for 24h; Ambient temperature;
  • 5
  • [ 64-17-5 ]
  • [ 1509-35-9 ]
  • [ 3082-86-8 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogenchloride for 3.5h; Heating;
  • 6
  • [ 32231-50-8 ]
  • [ 1509-35-9 ]
  • (2R,3S)-3-Methyl-2-((R)-2-methyl-butyrylamino)-pentanoic acid [ No CAS ]
  • 7
  • [ 1509-35-9 ]
  • 2-((tert-butoxycarbonyloxy)imino)-2-phenylacetonitrile [ No CAS ]
  • N-tert-butoxycarbonyl-D-alloisoleucine [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With triethylamine In water; acetone for 5h; Ambient temperature;
  • 8
  • [ 1509-35-9 ]
  • N-<(benzyloxy)carbonyl>-5-norbornene-2,3-dicarboximide [ No CAS ]
  • N-benzyloxycarbonylamino-D-alloisoleucine [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With triethylamine In tetrahydrofuran; water 0 deg C, 30 min, room temperature, 24 h;
  • 9
  • [ 3107-04-8 ]
  • [ 1509-34-8 ]
  • [ 1509-35-9 ]
YieldReaction ConditionsOperation in experiment
With tetramethylorthosilicate In ethanol; water at 20℃;
  • 10
  • [ 1509-35-9 ]
  • [ 108-24-7 ]
  • [ 54831-20-8 ]
YieldReaction ConditionsOperation in experiment
72% With sodium hydroxide at 0℃; for 1.5h;
  • 11
  • (2R/S,3S)-2-azido-3-methylpentanoic acid [ No CAS ]
  • [ 73-32-5 ]
  • [ 1509-35-9 ]
YieldReaction ConditionsOperation in experiment
With hydrogen In methanol; ethyl acetate for 18h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
  • 12
  • [ 50-00-0 ]
  • [ 1509-35-9 ]
  • [ 50673-48-8 ]
YieldReaction ConditionsOperation in experiment
Stage #1: formaldehyd; D-alloisoleucine With cyclopenta-1,3-diene In water at 20℃; for 16h; Stage #2: With triethylsilane; trifluoroacetic acid In chloroform at 20℃; for 6h;
  • 13
  • [ 1509-35-9 ]
  • [ 32653-36-4 ]
YieldReaction ConditionsOperation in experiment
87% With hydrogen bromide; sodium nitrite In water at 0℃; for 2.5h; 5.A The (2R,3S)-2-amino-3-methylpentanoic acid (D-allo-isoleucine, 1g, 7.62 mmol) was dissolved in a mixture of HBr 48% ( 6.95 mL, 61 mmol) and H2O (10.5 mL). At 0° C., a solution of NaNO2 (1.68 g, 24.4 mmol) in H2O (5 mL) was added over a period of 30 min. The reaction was stirred for two hours. The reaction mixture was degassed in vacuo and extracted with EtOAc (2×20mL). The extracts were washed with water (15 mL), dried (Na2SO4), filtered and evaporated to give 1.3 g (87% yield) of the (2R, 3S)-2-bromo-3-methylpentanoic acid as a light yellow oil.
With hydrogen bromide; potassium bromide; sodium nitrite
With hydrogen bromide; sodium nitrite In water at 0 - 20℃; for 16h; 3.1 Step 1:
(2R,3S)-2-bromo-3-methylpentanoic acid
To a solution of (2R,3S)-2-amino-3-methylpentanoic acid (1.0 g, 7.6 mmol) in HBr (40% in water, 8 mL) at 0° C. was added a solution of NaNO2 (0.78 g, 11.4 mmol) in H2O (4 mL) dropwise. The reaction mixture was stirred at room temperature for 16 hours. The solution was extracted with EtOAc (20 mL*2). The combined organic layers were dried over Na2SO4, filtered and the filtrate was concentrated under reduced pressure to give the crude product (2R,3S)-2-bromo-3-methylpentanoic acid as an orange oil (1.1 g). The crude product was used for the next step directly.
  • 14
  • [ 1509-35-9 ]
  • [ 142026-03-7 ]
YieldReaction ConditionsOperation in experiment
76% With triflic azide; potassium carbonate; copper(II) sulfate In methanol; dichloromethane; water at 20℃;
  • 15
  • [ 1509-35-9 ]
  • [ 75315-63-8 ]
  • N-benzyloxycarbonylamino-D-alloisoleucine [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With triethylamine In dichloromethane at 0 - 20℃;
99% With triethylamine In dichloromethane at 0 - 20℃;
  • 16
  • [ 1509-35-9 ]
  • [ 29745-04-8 ]
  • (2R,3S)-2-((1S,2R,6S,7R)-3,5-Dioxo-10-oxa-4-aza-tricyclo[5.2.1.02,6]dec-4-yl)-3-methyl-pentanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With triethylamine In toluene at 200℃; for 16h;
  • 17
  • [ 73-32-5 ]
  • [ 1509-35-9 ]
YieldReaction ConditionsOperation in experiment
87% With ammonia borane; Proteus myxofaciens
84% With salicylaldehyde; acetic acid In toluene at 100℃; for 3h; Reference example Synthesis of a 1: 1 epimer mixture of L-isoleucine and D-alloisoleucine was carried out by the method of JP-A 11-228512. 1.00 g (7.50 mmol) of L-isoleucine, 5 ml of toluene, 1.72 ml of acetic acid and 183.2 mg (1.50 mmol) of salicylaldehyde were charged in a flask and stirred at 100 ° C. for 3 hours. After the reaction solution was cooled to room temperature, the crystals were filtered and washed with 4 ml of toluene to obtain 837.3 mg (6.28 mmol, yield 84%) of a 1: 1 epimer mixture of L-isoleucine and D-alloisoleucine as white crystals Obtained.
Multi-step reaction with 6 steps 1.1: 90 percent / benzaldehyde; glacial acetic acid / 2 h / 100 °C 2.1: thionyl chloride / 7 h / 50 °C 2.2: NH3 / H2O / pH 9.5 2.3: 71 percent / HCl / diethyl ether / 0 °C 3.1: Na2CO3 / H2O; ethyl acetate / pH 9 / cooling 3.2: 94 percent / acetic anhydride / 23 h / 20 °C 4.1: 40 percent / alcalase; NaOH / H2O / 2.5 h / 39 °C / pH 7.8 / Enzymatic reaction 5.1: 87 percent / hydrochloric acid / 5 h / 90 °C 6.1: NaOH / dioxane; H2O / 1.5 h / Heating
Multi-step reaction with 6 steps 1.1: 90 percent / benzaldehyde; glacial acetic acid / 2 h / 100 °C 2.1: p-TsOH*H2O / toluene / 18 h / Heating 2.2: K2CO3 / H2O; ethyl acetate / pH 8.5 3.1: 96 percent / acetic anhydride / 3 h / 20 °C 4.1: 41 percent / alcalase; NaOH / H2O / 22.5 h / 39 °C / pH 7.8 / Enzymatic reaction 5.1: 85 percent / hydrochloric acid / 12 h / 90 °C 6.1: 90 percent / H2 / Pd/C / H2O; ethanol / 1.5 h / 3620.04 Torr
Multi-step reaction with 6 steps 1.1: 90 percent / benzaldehyde; glacial acetic acid / 2 h / 100 °C 2.1: p-TsOH*H2O / toluene / 18 h / Heating 2.2: K2CO3 / H2O; ethyl acetate / pH 8.5 3.1: 96 percent / DMAP; Et3N / 2.5 h / 20 °C 4.1: 50 percent / alcalase; NaOH / H2O / 3.3 h / 39 °C / pH 7.8 / Enzymatic reaction 5.1: 74 percent / H2 / Pd/C / ethanol / 2 h / 3102.89 Torr 6.1: HCl / dioxane; H2O / 8 h / Heating
With ammonium metavanadate; salicylaldehyde; sodium hydroxide In water for 6h; Reflux; 2.1. Epimerization of isoleucine General procedure: A round-bottom flask was loaded with isoleucine (1.31 g, 10 mmol), NaOH (0.4 g, 10 mmol) and water (5 mL). The mixture was gently heated until dissolution. Salicylaldehyde (0.011 mL, 0.1 mmol) and NH4VO3 (0.0112 g, 0.1 mmol) were added and the yellow solution (pH = 11) was heated under reflux 6 h. After this period the heating was carefully continued without reflux to evaporate approx. 1/2 of the solvent. Then the solution was cooled to room temperature, 20 mL of EtOH and 0.7 mL of acetic acid were added. The mixture was cooled in a freezer below 0 °C, white precipitate of isoleucine was filtered off, washed with EtOH and dried in air.
Multi-step reaction with 2 steps 1: acetic acid 2: water; hydrogenchloride / 80 °C
With acetaldehyde; acetic acid at 100℃; for 3h;

  • 18
  • [ 211686-27-0 ]
  • [ 1509-35-9 ]
YieldReaction ConditionsOperation in experiment
90% With hydrogen In ethanol; water for 1.5h;
  • 20
  • [ 3082-86-8 ]
  • [ 1509-35-9 ]
YieldReaction ConditionsOperation in experiment
50 mg With lithium hydroxide In ethanol at 20℃; for 0.5h;
  • 21
  • [ 1460-34-0 ]
  • [ 1509-35-9 ]
YieldReaction ConditionsOperation in experiment
With meso-2,6-D-diaminopimelic acid dehydrogenase mutant BC621; ammonium chloride; NADPH In various solvent(s) for 24h;
  • 22
  • [ 13139-17-8 ]
  • [ 1509-35-9 ]
  • N-benzyloxycarbonylamino-D-alloisoleucine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane at 0 - 20℃;
  • 23
  • [ 1509-35-9 ]
  • C17H25NO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: triethylamine / CH2Cl2 / 0 - 20 °C 2.1: EDAC*HCl; 4-dimethylaminopyridine / CH2Cl2 / 4.5 h / 0 - 20 °C 3.1: lithium diisopropylamide / tetrahydrofuran / 1 h / -78 °C 3.2: 3.42 g / tetrahydrofuran / 0.75 h / -78 °C 4.1: potassium borohydride / methanol / 0.83 h / -78 - 0 °C
  • 24
  • [ 1509-35-9 ]
  • [ 159407-39-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: triethylamine / CH2Cl2 / 0 - 20 °C 2.1: EDAC*HCl; 4-dimethylaminopyridine / CH2Cl2 / 4.5 h / 0 - 20 °C 3.1: lithium diisopropylamide / tetrahydrofuran / 1 h / -78 °C 3.2: 3.42 g / tetrahydrofuran / 0.75 h / -78 °C 4.1: potassium borohydride / methanol / 0.83 h / -78 - 0 °C
Multi-step reaction with 4 steps 1: 99 percent / Et3N / CH2Cl2 / 0 - 20 °C 2: EDAC*HCl; DMAP / CH2Cl2 / 4.5 h / 0 - 20 °C 3: 3.42 g / tetrahydrofuran / 0.75 h / -78 °C 4: potassium borohydride / methanol / 0.83 h / -78 - 0 °C
Multi-step reaction with 4 steps 1: 99 percent / Et3N / CH2Cl2 / 0 - 20 °C 2: EDAC*HCl; DMAP / CH2Cl2 / 0 - 20 °C 3: tetrahydrofuran / -78 °C 4: 99 percent / KBH4 / methanol / -30 - 0 °C
Multi-step reaction with 3 steps 1: 99 percent / Et3N / tetrahydrofuran; H2O / 0 deg C, 30 min, room temperature, 24 h 2: 37 percent / carbonyldiimidazole, LDA / tetrahydrofuran; hexane / 2 h / -78 - 0 °C 3: 96 percent / KBH4 / methanol / 0.25 h / 0 °C

  • 25
  • [ 1509-35-9 ]
  • [ 159360-04-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: triethylamine / CH2Cl2 / 0 - 20 °C 2.1: EDAC*HCl; 4-dimethylaminopyridine / CH2Cl2 / 4.5 h / 0 - 20 °C 3.1: lithium diisopropylamide / tetrahydrofuran / 1 h / -78 °C 3.2: 3.42 g / tetrahydrofuran / 0.75 h / -78 °C
Multi-step reaction with 3 steps 1: 99 percent / Et3N / CH2Cl2 / 0 - 20 °C 2: EDAC*HCl; DMAP / CH2Cl2 / 4.5 h / 0 - 20 °C 3: 3.42 g / tetrahydrofuran / 0.75 h / -78 °C
Multi-step reaction with 3 steps 1: 99 percent / Et3N / CH2Cl2 / 0 - 20 °C 2: EDAC*HCl; DMAP / CH2Cl2 / 0 - 20 °C 3: tetrahydrofuran / -78 °C
Multi-step reaction with 2 steps 1: 99 percent / Et3N / tetrahydrofuran; H2O / 0 deg C, 30 min, room temperature, 24 h 2: 37 percent / carbonyldiimidazole, LDA / tetrahydrofuran; hexane / 2 h / -78 - 0 °C

  • 26
  • [ 1509-35-9 ]
  • [ 250039-48-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / CH2Cl2 / 0 - 20 °C 2: EDAC*HCl; 4-dimethylaminopyridine / CH2Cl2 / 4.5 h / 0 - 20 °C
Multi-step reaction with 2 steps 1: 99 percent / Et3N / CH2Cl2 / 0 - 20 °C 2: EDAC*HCl; DMAP / CH2Cl2 / 4.5 h / 0 - 20 °C
Multi-step reaction with 2 steps 1: 99 percent / Et3N / CH2Cl2 / 0 - 20 °C 2: EDAC*HCl; DMAP / CH2Cl2 / 0 - 20 °C
  • 27
  • [ 841271-80-5 ]
  • [ 1509-35-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 70 percent / H2 / PI Pd / ethanol / 12 h / 20 °C 2: SmI2 / tetrahydrofuran; ethanol / 0.5 h / 20 °C 3: 50 mg / LiOH / ethanol / 0.5 h / 20 °C
  • 28
  • [ 841271-90-7 ]
  • [ 1509-35-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SmI2 / tetrahydrofuran; ethanol / 0.5 h / 20 °C 2: 50 mg / LiOH / ethanol / 0.5 h / 20 °C
  • 29
  • (2RS,3S)-2-amino-3-methylpentanoic acid [ No CAS ]
  • [ 1509-35-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: thionyl chloride / 7 h / 50 °C 1.2: NH3 / H2O / pH 9.5 1.3: 71 percent / HCl / diethyl ether / 0 °C 2.1: Na2CO3 / H2O; ethyl acetate / pH 9 / cooling 2.2: 94 percent / acetic anhydride / 23 h / 20 °C 3.1: 40 percent / alcalase; NaOH / H2O / 2.5 h / 39 °C / pH 7.8 / Enzymatic reaction 4.1: 87 percent / hydrochloric acid / 5 h / 90 °C 5.1: NaOH / dioxane; H2O / 1.5 h / Heating
Multi-step reaction with 5 steps 1.1: p-TsOH*H2O / toluene / 18 h / Heating 1.2: K2CO3 / H2O; ethyl acetate / pH 8.5 2.1: 96 percent / acetic anhydride / 3 h / 20 °C 3.1: 41 percent / alcalase; NaOH / H2O / 22.5 h / 39 °C / pH 7.8 / Enzymatic reaction 4.1: 85 percent / hydrochloric acid / 12 h / 90 °C 5.1: 90 percent / H2 / Pd/C / H2O; ethanol / 1.5 h / 3620.04 Torr
Multi-step reaction with 5 steps 1.1: p-TsOH*H2O / toluene / 18 h / Heating 1.2: K2CO3 / H2O; ethyl acetate / pH 8.5 2.1: 96 percent / DMAP; Et3N / 2.5 h / 20 °C 3.1: 50 percent / alcalase; NaOH / H2O / 3.3 h / 39 °C / pH 7.8 / Enzymatic reaction 4.1: 74 percent / H2 / Pd/C / ethanol / 2 h / 3102.89 Torr 5.1: HCl / dioxane; H2O / 8 h / Heating
  • 30
  • (S)-2-Amino-3-methyl-pentanoic acid benzyl ester [ No CAS ]
  • [ 1509-35-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 96 percent / acetic anhydride / 3 h / 20 °C 2: 41 percent / alcalase; NaOH / H2O / 22.5 h / 39 °C / pH 7.8 / Enzymatic reaction 3: 85 percent / hydrochloric acid / 12 h / 90 °C 4: 90 percent / H2 / Pd/C / H2O; ethanol / 1.5 h / 3620.04 Torr
Multi-step reaction with 4 steps 1: 96 percent / DMAP; Et3N / 2.5 h / 20 °C 2: 50 percent / alcalase; NaOH / H2O / 3.3 h / 39 °C / pH 7.8 / Enzymatic reaction 3: 74 percent / H2 / Pd/C / ethanol / 2 h / 3102.89 Torr 4: HCl / dioxane; H2O / 8 h / Heating
  • 31
  • [ 1509-35-9 ]
  • [ 505094-55-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: NaOH / H2O / 0.58 h / 0 - 20 °C 2: BF3*Et2O / CH2Cl2; cyclohexane / 15 h / 20 °C
  • 32
  • [ 1509-35-9 ]
  • 1,1-dimethylethyl N-(diphenylmethylene)-D-alloisoleucinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: NaOH / H2O / 0.58 h / 0 - 20 °C 2.1: BF3*Et2O / CH2Cl2; cyclohexane / 15 h / 20 °C 3.1: Pd/C; H2 / AcOH / methanol 3.2: CH2Cl2 / 20 °C
  • 33
  • [ 1509-35-9 ]
  • [ 250211-78-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 15 steps 1: 99 percent / Et3N / CH2Cl2 / 0 - 20 °C 2: EDAC*HCl; DMAP / CH2Cl2 / 0 - 20 °C 3: tetrahydrofuran / -78 °C 4: 99 percent / KBH4 / methanol / -30 - 0 °C 5: 94 percent / 2,6-lutidine / CH2Cl2 / 20 °C 6: 95 percent / aq. NaOH / tetrahydrofuran; methanol / 0 - 20 °C 7: 65 percent / DCC; DMAP / 0 - 20 °C 8: 100 percent / Pd(PPh3)4; morpholine / tetrahydrofuran / 20 °C 9: EDAC*HCl; DMAP / CH2Cl2 10: 96 percent / DIEA; DMAP / CH2Cl2 / 0 - 20 °C 11: MgBr2*Et2O / CH2Cl2 / -15 - 0 °C 12: H2 / Pd/C / ethyl acetate; methanol / 20 °C 13: HATU; DIEA / dimethylformamide / 20 °C 14: HCl(g) / ethyl acetate / -30 - 0 °C 15: BOP; NMM / CH2Cl2 / 0 - 20 °C
Multi-step reaction with 14 steps 1: 99 percent / Et3N / CH2Cl2 / 0 - 20 °C 2: EDAC*HCl; DMAP / CH2Cl2 / 0 - 20 °C 3: tetrahydrofuran / -78 °C 4: 99 percent / KBH4 / methanol / -30 - 0 °C 5: 94 percent / 2,6-lutidine / CH2Cl2 / 20 °C 6: 95 percent / aq. NaOH / tetrahydrofuran; methanol / 0 - 20 °C 7: 65 percent / DCC; DMAP / 0 - 20 °C 8: 100 percent / Pd(PPh3)4; morpholine / tetrahydrofuran / 20 °C 9: 30 percent / PyBrOP; DIEA / CH2Cl2 10: MgBr2*Et2O / CH2Cl2 / -15 - 0 °C 11: H2 / Pd/C / ethyl acetate; methanol / 20 °C 12: HATU; DIEA / dimethylformamide / 20 °C 13: HCl(g) / ethyl acetate / -30 - 0 °C 14: BOP; NMM / CH2Cl2 / 0 - 20 °C
  • 34
  • [ 1509-35-9 ]
  • [ 779313-73-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 14 steps 1: 99 percent / Et3N / CH2Cl2 / 0 - 20 °C 2: EDAC*HCl; DMAP / CH2Cl2 / 0 - 20 °C 3: tetrahydrofuran / -78 °C 4: 99 percent / KBH4 / methanol / -30 - 0 °C 5: 94 percent / 2,6-lutidine / CH2Cl2 / 20 °C 6: 95 percent / aq. NaOH / tetrahydrofuran; methanol / 0 - 20 °C 7: 65 percent / DCC; DMAP / 0 - 20 °C 8: 100 percent / Pd(PPh3)4; morpholine / tetrahydrofuran / 20 °C 9: EDAC*HCl; DMAP / CH2Cl2 10: 96 percent / DIEA; DMAP / CH2Cl2 / 0 - 20 °C 11: MgBr2*Et2O / CH2Cl2 / -15 - 0 °C 12: H2 / Pd/C / ethyl acetate; methanol / 20 °C 13: HATU; DIEA / dimethylformamide / 20 °C 14: HCl(g) / ethyl acetate / -30 - 0 °C
Multi-step reaction with 13 steps 1: 99 percent / Et3N / CH2Cl2 / 0 - 20 °C 2: EDAC*HCl; DMAP / CH2Cl2 / 0 - 20 °C 3: tetrahydrofuran / -78 °C 4: 99 percent / KBH4 / methanol / -30 - 0 °C 5: 94 percent / 2,6-lutidine / CH2Cl2 / 20 °C 6: 95 percent / aq. NaOH / tetrahydrofuran; methanol / 0 - 20 °C 7: 65 percent / DCC; DMAP / 0 - 20 °C 8: 100 percent / Pd(PPh3)4; morpholine / tetrahydrofuran / 20 °C 9: 30 percent / PyBrOP; DIEA / CH2Cl2 10: MgBr2*Et2O / CH2Cl2 / -15 - 0 °C 11: H2 / Pd/C / ethyl acetate; methanol / 20 °C 12: HATU; DIEA / dimethylformamide / 20 °C 13: HCl(g) / ethyl acetate / -30 - 0 °C
  • 35
  • [ 1509-35-9 ]
  • (2R,3S)-2-((S)-sec-Butyl)-5-oxo-3-triisopropylsilanyloxy-pyrrolidine-1-carboxylic acid benzyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 99 percent / Et3N / CH2Cl2 / 0 - 20 °C 2: EDAC*HCl; DMAP / CH2Cl2 / 0 - 20 °C 3: tetrahydrofuran / -78 °C 4: 99 percent / KBH4 / methanol / -30 - 0 °C 5: 94 percent / 2,6-lutidine / CH2Cl2 / 20 °C 6: 95 percent / aq. NaOH / tetrahydrofuran; methanol / 0 - 20 °C 7: 45 percent / IPCF; DMAP; Et3N / 0 °C
  • 36
  • [ 1509-35-9 ]
  • [ 250039-49-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 99 percent / Et3N / CH2Cl2 / 0 - 20 °C 2: EDAC*HCl; DMAP / CH2Cl2 / 0 - 20 °C 3: tetrahydrofuran / -78 °C 4: 99 percent / KBH4 / methanol / -30 - 0 °C 5: 94 percent / 2,6-lutidine / CH2Cl2 / 20 °C
  • 37
  • [ 1509-35-9 ]
  • [ 250039-50-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 99 percent / Et3N / CH2Cl2 / 0 - 20 °C 2: EDAC*HCl; DMAP / CH2Cl2 / 0 - 20 °C 3: tetrahydrofuran / -78 °C 4: 99 percent / KBH4 / methanol / -30 - 0 °C 5: 94 percent / 2,6-lutidine / CH2Cl2 / 20 °C 6: 95 percent / aq. NaOH / tetrahydrofuran; methanol / 0 - 20 °C
  • 38
  • [ 1509-35-9 ]
  • [ 250039-47-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: 99 percent / Et3N / CH2Cl2 / 0 - 20 °C 2: EDAC*HCl; DMAP / CH2Cl2 / 0 - 20 °C 3: tetrahydrofuran / -78 °C 4: 99 percent / KBH4 / methanol / -30 - 0 °C 5: 94 percent / 2,6-lutidine / CH2Cl2 / 20 °C 6: 95 percent / aq. NaOH / tetrahydrofuran; methanol / 0 - 20 °C 7: 65 percent / DCC; DMAP / 0 - 20 °C 8: 100 percent / Pd(PPh3)4; morpholine / tetrahydrofuran / 20 °C
  • 39
  • [ 1509-35-9 ]
  • [ 250039-51-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 99 percent / Et3N / CH2Cl2 / 0 - 20 °C 2: EDAC*HCl; DMAP / CH2Cl2 / 0 - 20 °C 3: tetrahydrofuran / -78 °C 4: 99 percent / KBH4 / methanol / -30 - 0 °C 5: 94 percent / 2,6-lutidine / CH2Cl2 / 20 °C 6: 95 percent / aq. NaOH / tetrahydrofuran; methanol / 0 - 20 °C 7: 65 percent / DCC; DMAP / 0 - 20 °C
  • 40
  • [ 1509-35-9 ]
  • (3S,4R,5S)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-heptanoic acid (S)-2-methyl-1-(2-trimethylsilanyl-ethoxymethoxycarbonyl)-propyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 99 percent / Et3N / CH2Cl2 / 0 - 20 °C 2: EDAC*HCl; DMAP / CH2Cl2 / 0 - 20 °C 3: tetrahydrofuran / -78 °C 4: 99 percent / KBH4 / methanol / -30 - 0 °C 5: 94 percent / 2,6-lutidine / CH2Cl2 / 20 °C 6: 95 percent / aq. NaOH / tetrahydrofuran; methanol / 0 - 20 °C 7: 15 percent / IPCF; DMAP; Et3N / 0 °C
  • 41
  • [ 1509-35-9 ]
  • [ 250039-53-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: 99 percent / Et3N / CH2Cl2 / 0 - 20 °C 2: EDAC*HCl; DMAP / CH2Cl2 / 0 - 20 °C 3: tetrahydrofuran / -78 °C 4: 99 percent / KBH4 / methanol / -30 - 0 °C 5: 94 percent / 2,6-lutidine / CH2Cl2 / 20 °C 6: 95 percent / aq. NaOH / tetrahydrofuran; methanol / 0 - 20 °C 7: 65 percent / DCC; DMAP / 0 - 20 °C 8: 100 percent / Pd(PPh3)4; morpholine / tetrahydrofuran / 20 °C 9: EDAC*HCl; DMAP / CH2Cl2
  • 42
  • [ 1509-35-9 ]
  • [13-<i>sec</i>-butyl-12-(diisopropyl-methyl-silanyloxy)-5-isobutyl-8-isopropyl-20-(4-methoxy-benzyl)-17,21-dimethyl-4,7,10,15,19,22-hexaoxo-eicosahydro-9,18-dioxa-3a,6,14,21-tetraaza-cyclopentacycloheneicosen-16-yl]-carbamic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 13 steps 1: 99 percent / Et3N / CH2Cl2 / 0 - 20 °C 2: EDAC*HCl; DMAP / CH2Cl2 / 0 - 20 °C 3: tetrahydrofuran / -78 °C 4: 99 percent / KBH4 / methanol / -30 - 0 °C 5: 94 percent / 2,6-lutidine / CH2Cl2 / 20 °C 6: 95 percent / aq. NaOH / tetrahydrofuran; methanol / 0 - 20 °C 7: 65 percent / DCC; DMAP / 0 - 20 °C 8: 100 percent / Pd(PPh3)4; morpholine / tetrahydrofuran / 20 °C 9: EDAC*HCl; DMAP / CH2Cl2 10: 96 percent / DIEA; DMAP / CH2Cl2 / 0 - 20 °C 11: MgBr2*Et2O / CH2Cl2 / -15 - 0 °C 12: H2 / Pd/C / ethyl acetate; methanol / 20 °C 13: HATU; DIEA / dimethylformamide / 20 °C
Multi-step reaction with 12 steps 1: 99 percent / Et3N / CH2Cl2 / 0 - 20 °C 2: EDAC*HCl; DMAP / CH2Cl2 / 0 - 20 °C 3: tetrahydrofuran / -78 °C 4: 99 percent / KBH4 / methanol / -30 - 0 °C 5: 94 percent / 2,6-lutidine / CH2Cl2 / 20 °C 6: 95 percent / aq. NaOH / tetrahydrofuran; methanol / 0 - 20 °C 7: 65 percent / DCC; DMAP / 0 - 20 °C 8: 100 percent / Pd(PPh3)4; morpholine / tetrahydrofuran / 20 °C 9: 30 percent / PyBrOP; DIEA / CH2Cl2 10: MgBr2*Et2O / CH2Cl2 / -15 - 0 °C 11: H2 / Pd/C / ethyl acetate; methanol / 20 °C 12: HATU; DIEA / dimethylformamide / 20 °C
  • 43
  • [ 1509-35-9 ]
  • [ 345664-76-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 12 steps 1: 99 percent / Et3N / CH2Cl2 / 0 - 20 °C 2: EDAC*HCl; DMAP / CH2Cl2 / 0 - 20 °C 3: tetrahydrofuran / -78 °C 4: 99 percent / KBH4 / methanol / -30 - 0 °C 5: 94 percent / 2,6-lutidine / CH2Cl2 / 20 °C 6: 95 percent / aq. NaOH / tetrahydrofuran; methanol / 0 - 20 °C 7: 65 percent / DCC; DMAP / 0 - 20 °C 8: 100 percent / Pd(PPh3)4; morpholine / tetrahydrofuran / 20 °C 9: EDAC*HCl; DMAP / CH2Cl2 10: 96 percent / DIEA; DMAP / CH2Cl2 / 0 - 20 °C 11: MgBr2*Et2O / CH2Cl2 / -15 - 0 °C 12: H2 / Pd/C / ethyl acetate; methanol / 20 °C
Multi-step reaction with 11 steps 1: 99 percent / Et3N / CH2Cl2 / 0 - 20 °C 2: EDAC*HCl; DMAP / CH2Cl2 / 0 - 20 °C 3: tetrahydrofuran / -78 °C 4: 99 percent / KBH4 / methanol / -30 - 0 °C 5: 94 percent / 2,6-lutidine / CH2Cl2 / 20 °C 6: 95 percent / aq. NaOH / tetrahydrofuran; methanol / 0 - 20 °C 7: 65 percent / DCC; DMAP / 0 - 20 °C 8: 100 percent / Pd(PPh3)4; morpholine / tetrahydrofuran / 20 °C 9: 30 percent / PyBrOP; DIEA / CH2Cl2 10: MgBr2*Et2O / CH2Cl2 / -15 - 0 °C 11: H2 / Pd/C / ethyl acetate; methanol / 20 °C
  • 44
  • [ 1509-35-9 ]
  • N-L-prolyl [Hiv2]didemnin A [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 16 steps 1: 99 percent / Et3N / CH2Cl2 / 0 - 20 °C 2: EDAC*HCl; DMAP / CH2Cl2 / 0 - 20 °C 3: tetrahydrofuran / -78 °C 4: 99 percent / KBH4 / methanol / -30 - 0 °C 5: 94 percent / 2,6-lutidine / CH2Cl2 / 20 °C 6: 95 percent / aq. NaOH / tetrahydrofuran; methanol / 0 - 20 °C 7: 65 percent / DCC; DMAP / 0 - 20 °C 8: 100 percent / Pd(PPh3)4; morpholine / tetrahydrofuran / 20 °C 9: EDAC*HCl; DMAP / CH2Cl2 10: 96 percent / DIEA; DMAP / CH2Cl2 / 0 - 20 °C 11: MgBr2*Et2O / CH2Cl2 / -15 - 0 °C 12: H2 / Pd/C / ethyl acetate; methanol / 20 °C 13: HATU; DIEA / dimethylformamide / 20 °C 14: HCl(g) / ethyl acetate / -30 - 0 °C 15: BOP; NMM / CH2Cl2 / 0 - 20 °C 16: 84 percent / H2 / 10 percent Pd/C / methanol; ethyl acetate
Multi-step reaction with 15 steps 1: 99 percent / Et3N / CH2Cl2 / 0 - 20 °C 2: EDAC*HCl; DMAP / CH2Cl2 / 0 - 20 °C 3: tetrahydrofuran / -78 °C 4: 99 percent / KBH4 / methanol / -30 - 0 °C 5: 94 percent / 2,6-lutidine / CH2Cl2 / 20 °C 6: 95 percent / aq. NaOH / tetrahydrofuran; methanol / 0 - 20 °C 7: 65 percent / DCC; DMAP / 0 - 20 °C 8: 100 percent / Pd(PPh3)4; morpholine / tetrahydrofuran / 20 °C 9: 30 percent / PyBrOP; DIEA / CH2Cl2 10: MgBr2*Et2O / CH2Cl2 / -15 - 0 °C 11: H2 / Pd/C / ethyl acetate; methanol / 20 °C 12: HATU; DIEA / dimethylformamide / 20 °C 13: HCl(g) / ethyl acetate / -30 - 0 °C 14: BOP; NMM / CH2Cl2 / 0 - 20 °C 15: 84 percent / H2 / 10 percent Pd/C / methanol; ethyl acetate
  • 45
  • [ 1509-35-9 ]
  • [ 345664-75-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1: 99 percent / Et3N / CH2Cl2 / 0 - 20 °C 2: EDAC*HCl; DMAP / CH2Cl2 / 0 - 20 °C 3: tetrahydrofuran / -78 °C 4: 99 percent / KBH4 / methanol / -30 - 0 °C 5: 94 percent / 2,6-lutidine / CH2Cl2 / 20 °C 6: 95 percent / aq. NaOH / tetrahydrofuran; methanol / 0 - 20 °C 7: 65 percent / DCC; DMAP / 0 - 20 °C 8: 100 percent / Pd(PPh3)4; morpholine / tetrahydrofuran / 20 °C 9: EDAC*HCl; DMAP / CH2Cl2 10: 96 percent / DIEA; DMAP / CH2Cl2 / 0 - 20 °C 11: MgBr2*Et2O / CH2Cl2 / -15 - 0 °C
Multi-step reaction with 10 steps 1: 99 percent / Et3N / CH2Cl2 / 0 - 20 °C 2: EDAC*HCl; DMAP / CH2Cl2 / 0 - 20 °C 3: tetrahydrofuran / -78 °C 4: 99 percent / KBH4 / methanol / -30 - 0 °C 5: 94 percent / 2,6-lutidine / CH2Cl2 / 20 °C 6: 95 percent / aq. NaOH / tetrahydrofuran; methanol / 0 - 20 °C 7: 65 percent / DCC; DMAP / 0 - 20 °C 8: 100 percent / Pd(PPh3)4; morpholine / tetrahydrofuran / 20 °C 9: 30 percent / PyBrOP; DIEA / CH2Cl2 10: MgBr2*Et2O / CH2Cl2 / -15 - 0 °C
  • 46
  • [ 1509-35-9 ]
  • dehydrotamandarin A [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 15 steps 1: 99 percent / Et3N / CH2Cl2 / 0 - 20 °C 2: EDAC*HCl; DMAP / CH2Cl2 / 0 - 20 °C 3: tetrahydrofuran / -78 °C 4: 99 percent / KBH4 / methanol / -30 - 0 °C 5: 94 percent / 2,6-lutidine / CH2Cl2 / 20 °C 6: 95 percent / aq. NaOH / tetrahydrofuran; methanol / 0 - 20 °C 7: 65 percent / DCC; DMAP / 0 - 20 °C 8: 100 percent / Pd(PPh3)4; morpholine / tetrahydrofuran / 20 °C 9: EDAC*HCl; DMAP / CH2Cl2 10: 96 percent / DIEA; DMAP / CH2Cl2 / 0 - 20 °C 11: MgBr2*Et2O / CH2Cl2 / -15 - 0 °C 12: H2 / Pd/C / ethyl acetate; methanol / 20 °C 13: HATU; DIEA / dimethylformamide / 20 °C 14: HCl(g) / ethyl acetate / -30 - 0 °C 15: BOP; NMM / CH2Cl2
Multi-step reaction with 14 steps 1: 99 percent / Et3N / CH2Cl2 / 0 - 20 °C 2: EDAC*HCl; DMAP / CH2Cl2 / 0 - 20 °C 3: tetrahydrofuran / -78 °C 4: 99 percent / KBH4 / methanol / -30 - 0 °C 5: 94 percent / 2,6-lutidine / CH2Cl2 / 20 °C 6: 95 percent / aq. NaOH / tetrahydrofuran; methanol / 0 - 20 °C 7: 65 percent / DCC; DMAP / 0 - 20 °C 8: 100 percent / Pd(PPh3)4; morpholine / tetrahydrofuran / 20 °C 9: 30 percent / PyBrOP; DIEA / CH2Cl2 10: MgBr2*Et2O / CH2Cl2 / -15 - 0 °C 11: H2 / Pd/C / ethyl acetate; methanol / 20 °C 12: HATU; DIEA / dimethylformamide / 20 °C 13: HCl(g) / ethyl acetate / -30 - 0 °C 14: BOP; NMM / CH2Cl2
  • 47
  • [ 1509-35-9 ]
  • [ 345664-71-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 15 steps 1: 99 percent / Et3N / CH2Cl2 / 0 - 20 °C 2: EDAC*HCl; DMAP / CH2Cl2 / 0 - 20 °C 3: tetrahydrofuran / -78 °C 4: 99 percent / KBH4 / methanol / -30 - 0 °C 5: 94 percent / 2,6-lutidine / CH2Cl2 / 20 °C 6: 95 percent / aq. NaOH / tetrahydrofuran; methanol / 0 - 20 °C 7: 65 percent / DCC; DMAP / 0 - 20 °C 8: 100 percent / Pd(PPh3)4; morpholine / tetrahydrofuran / 20 °C 9: EDAC*HCl; DMAP / CH2Cl2 10: 96 percent / DIEA; DMAP / CH2Cl2 / 0 - 20 °C 11: MgBr2*Et2O / CH2Cl2 / -15 - 0 °C 12: H2 / Pd/C / ethyl acetate; methanol / 20 °C 13: HATU; DIEA / dimethylformamide / 20 °C 14: HCl(g) / ethyl acetate / -30 - 0 °C 15: BOP; NMM / CH2Cl2 / 0 - 20 °C
Multi-step reaction with 14 steps 1: 99 percent / Et3N / CH2Cl2 / 0 - 20 °C 2: EDAC*HCl; DMAP / CH2Cl2 / 0 - 20 °C 3: tetrahydrofuran / -78 °C 4: 99 percent / KBH4 / methanol / -30 - 0 °C 5: 94 percent / 2,6-lutidine / CH2Cl2 / 20 °C 6: 95 percent / aq. NaOH / tetrahydrofuran; methanol / 0 - 20 °C 7: 65 percent / DCC; DMAP / 0 - 20 °C 8: 100 percent / Pd(PPh3)4; morpholine / tetrahydrofuran / 20 °C 9: 30 percent / PyBrOP; DIEA / CH2Cl2 10: MgBr2*Et2O / CH2Cl2 / -15 - 0 °C 11: H2 / Pd/C / ethyl acetate; methanol / 20 °C 12: HATU; DIEA / dimethylformamide / 20 °C 13: HCl(g) / ethyl acetate / -30 - 0 °C 14: BOP; NMM / CH2Cl2 / 0 - 20 °C
  • 48
  • [ 1509-35-9 ]
  • [ 250039-54-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1: 99 percent / Et3N / CH2Cl2 / 0 - 20 °C 2: EDAC*HCl; DMAP / CH2Cl2 / 0 - 20 °C 3: tetrahydrofuran / -78 °C 4: 99 percent / KBH4 / methanol / -30 - 0 °C 5: 94 percent / 2,6-lutidine / CH2Cl2 / 20 °C 6: 95 percent / aq. NaOH / tetrahydrofuran; methanol / 0 - 20 °C 7: 65 percent / DCC; DMAP / 0 - 20 °C 8: 100 percent / Pd(PPh3)4; morpholine / tetrahydrofuran / 20 °C 9: EDAC*HCl; DMAP / CH2Cl2 10: 96 percent / DIEA; DMAP / CH2Cl2 / 0 - 20 °C
Multi-step reaction with 9 steps 1: 99 percent / Et3N / CH2Cl2 / 0 - 20 °C 2: EDAC*HCl; DMAP / CH2Cl2 / 0 - 20 °C 3: tetrahydrofuran / -78 °C 4: 99 percent / KBH4 / methanol / -30 - 0 °C 5: 94 percent / 2,6-lutidine / CH2Cl2 / 20 °C 6: 95 percent / aq. NaOH / tetrahydrofuran; methanol / 0 - 20 °C 7: 65 percent / DCC; DMAP / 0 - 20 °C 8: 100 percent / Pd(PPh3)4; morpholine / tetrahydrofuran / 20 °C 9: 30 percent / PyBrOP; DIEA / CH2Cl2
  • 49
  • [ 1509-35-9 ]
  • Gly-D-allo-IlePhy [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 76 percent / triflyl azide; K2CO3; CuSO4*5H2O / H2O; methanol; CH2Cl2 / 20 °C
  • 50
  • [ 1565-80-6 ]
  • [ 1509-35-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: TEMPO, KBr, NaOCl / CH2Cl2 / 0 - 20 °C 2: 1.) LiHMDS / 1.) THF, a) -78 deg C, 10 min, b) RT, 3.5 h, 2.) THF, -78 deg C 3: tetrahydrofuran / 1 h / -78 - 20 °C 4: 98 percent / 6N aq. HCl / 3.5 h / Heating
Multi-step reaction with 8 steps 1: 70 percent / pyridine / 24 h / Ambient temperature 2: 93 percent / dimethylformamide / 2.5 h / 120 °C 3: 99 percent / hydrazine, HCl / ethanol / 4 h / Heating 4: 69 percent / KOH 5: 84 percent / sat. Na2CO3 / diethyl ether / 0.5 h 6: 95 percent / electrolyte Bu4NBF4 / 1.13 h / 10 °C / Pt-anode 7: SnCl4 / H2O / 48 h / Ambient temperature 8: 12 N HCl, DOWEX 50(H+) / 24 h / 100 - 110 °C
Multi-step reaction with 8 steps 1: 70 percent / pyridine / 24 h / Ambient temperature 2: 93 percent / dimethylformamide / 2.5 h / 120 °C 3: 99 percent / hydrazine, HCl / ethanol / 4 h / Heating 4: 69 percent / KOH 5: 80 percent / 3 h / Heating 6: 95 percent / electrolyte Bu4NBF4 / 1.13 h / 10 °C / Pt-anode 7: SnCl4 / H2O / 48 h / Ambient temperature 8: 12 N HCl, DOWEX 50(H+) / 24 h / 100 - 110 °C
Multi-step reaction with 8 steps 1: 70 percent / pyridine / 24 h / Ambient temperature 2: 93 percent / dimethylformamide / 2.5 h / 120 °C 3: 99 percent / hydrazine, HCl / ethanol / 4 h / Heating 4: 69 percent / KOH 5: 88.5 percent / 2 h / Heating 6: 95 percent / Bu4NBF4 electrolyte / 0.8 h / 10 °C / Pt-anode 7: SnCl4 / H2O / 48 h / Ambient temperature 8: 12 N HCl, DOWEX 50(H+) / 24 h / 100 - 110 °C
Multi-step reaction with 8 steps 1: 80 percent / PPh3, CBr4 / benzene / 3 h / Heating 2: 50 percent / various solvent(s) / 24 h / 85 °C 3: 90 percent / 1 N HCl / various solvent(s) 4: 69 percent / KOH 5: 84 percent / sat. Na2CO3 / diethyl ether / 0.5 h 6: 95 percent / electrolyte Bu4NBF4 / 1.13 h / 10 °C / Pt-anode 7: SnCl4 / H2O / 48 h / Ambient temperature 8: 12 N HCl, DOWEX 50(H+) / 24 h / 100 - 110 °C
Multi-step reaction with 8 steps 1: 80 percent / PPh3, CBr4 / benzene / 3 h / Heating 2: 50 percent / various solvent(s) / 24 h / 85 °C 3: 90 percent / 1 N HCl / various solvent(s) 4: 69 percent / KOH 5: 80 percent / 3 h / Heating 6: 95 percent / electrolyte Bu4NBF4 / 1.13 h / 10 °C / Pt-anode 7: SnCl4 / H2O / 48 h / Ambient temperature 8: 12 N HCl, DOWEX 50(H+) / 24 h / 100 - 110 °C
Multi-step reaction with 8 steps 1: 80 percent / PPh3, CBr4 / benzene / 3 h / Heating 2: 50 percent / various solvent(s) / 24 h / 85 °C 3: 90 percent / 1 N HCl / various solvent(s) 4: 69 percent / KOH 5: 88.5 percent / 2 h / Heating 6: 95 percent / Bu4NBF4 electrolyte / 0.8 h / 10 °C / Pt-anode 7: SnCl4 / H2O / 48 h / Ambient temperature 8: 12 N HCl, DOWEX 50(H+) / 24 h / 100 - 110 °C

  • 51
  • [ 1730-97-8 ]
  • [ 1509-35-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1.) LiHMDS / 1.) THF, a) -78 deg C, 10 min, b) RT, 3.5 h, 2.) THF, -78 deg C 2: tetrahydrofuran / 1 h / -78 - 20 °C 3: 98 percent / 6N aq. HCl / 3.5 h / Heating
Multi-step reaction with 9 steps 1: 76 percent / aq. NaOH / dimethylformamide / 2 h / -10 - 5 °C 2: 45 percent / aq, NaOH, NaN3 / 1,2-dimethoxy-ethane / 24 h / Ambient temperature 3: H2 / Pd-C / ethyl acetate; methanol / 18 h / 760 Torr / Ambient temperature 4: 59 percent / aq. H2SO4, NaNO2 / 0 deg C, 2 h, room temperature, 16 h 5: 95 percent / diethyl ether 6: 72 percent / pyridine / 48 h / 4 °C 7: 2.53 g / NaN3 / dimethylformamide / 30 h / 50 °C 8: 79 percent / H2, HCl / Pd-C / ethanol / 18 h / 760 Torr / Ambient temperature 9: 0.41 g / aq. NaOH / 6 h / Ambient temperature
Multi-step reaction with 3 steps 1: 76 percent / aq. NaOH / dimethylformamide / 2 h / -10 - 5 °C 2: 45 percent / aq, NaOH, NaN3 / 1,2-dimethoxy-ethane / 24 h / Ambient temperature 3: H2 / Pd-C / ethyl acetate; methanol / 18 h / 760 Torr / Ambient temperature
  • 52
  • [ 1565-80-6 ]
  • [ 1509-35-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1: PCC, Al / CHCl3 / 2 h / Ambient temperature 2: 76 percent / aq. NaOH / dimethylformamide / 2 h / -10 - 5 °C 3: 45 percent / aq, NaOH, NaN3 / 1,2-dimethoxy-ethane / 24 h / Ambient temperature 4: H2 / Pd-C / ethyl acetate; methanol / 18 h / 760 Torr / Ambient temperature 5: 59 percent / aq. H2SO4, NaNO2 / 0 deg C, 2 h, room temperature, 16 h 6: 95 percent / diethyl ether 7: 72 percent / pyridine / 48 h / 4 °C 8: 2.53 g / NaN3 / dimethylformamide / 30 h / 50 °C 9: 79 percent / H2, HCl / Pd-C / ethanol / 18 h / 760 Torr / Ambient temperature 10: 0.41 g / aq. NaOH / 6 h / Ambient temperature
Multi-step reaction with 4 steps 1: PCC, Al / CHCl3 / 2 h / Ambient temperature 2: 76 percent / aq. NaOH / dimethylformamide / 2 h / -10 - 5 °C 3: 45 percent / aq, NaOH, NaN3 / 1,2-dimethoxy-ethane / 24 h / Ambient temperature 4: H2 / Pd-C / ethyl acetate; methanol / 18 h / 760 Torr / Ambient temperature
  • 53
  • (S)-1,1,1-Trichloro-3-methyl-pentan-2-ol [ No CAS ]
  • [ 1509-35-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: 45 percent / aq, NaOH, NaN3 / 1,2-dimethoxy-ethane / 24 h / Ambient temperature 2: H2 / Pd-C / ethyl acetate; methanol / 18 h / 760 Torr / Ambient temperature 3: 59 percent / aq. H2SO4, NaNO2 / 0 deg C, 2 h, room temperature, 16 h 4: 95 percent / diethyl ether 5: 72 percent / pyridine / 48 h / 4 °C 6: 2.53 g / NaN3 / dimethylformamide / 30 h / 50 °C 7: 79 percent / H2, HCl / Pd-C / ethanol / 18 h / 760 Torr / Ambient temperature 8: 0.41 g / aq. NaOH / 6 h / Ambient temperature
Multi-step reaction with 2 steps 1: 45 percent / aq, NaOH, NaN3 / 1,2-dimethoxy-ethane / 24 h / Ambient temperature 2: H2 / Pd-C / ethyl acetate; methanol / 18 h / 760 Torr / Ambient temperature
  • 54
  • 2-Amino-N-((E)-but-2-enyl)-N-((S)-1-phenyl-ethyl)-acetamide [ No CAS ]
  • [ 1509-35-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1) lithium hexamethyldisilazide / 1) toluene, -78 deg C, 30 min, 2) r.t., 15 h 2: H2 / 10 percent Pd-C / methanol 3: 6 N HCl / 3.5 h / 160 °C
  • 55
  • [ 143097-97-6 ]
  • [ 1509-35-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: H2 / 10 percent Pd-C / methanol 2: 6 N HCl / 3.5 h / 160 °C
  • 56
  • [ 34985-37-0 ]
  • [ 1509-35-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 84 percent / sat. Na2CO3 / diethyl ether / 0.5 h 2: 95 percent / electrolyte Bu4NBF4 / 1.13 h / 10 °C / Pt-anode 3: SnCl4 / H2O / 48 h / Ambient temperature 4: 12 N HCl, DOWEX 50(H+) / 24 h / 100 - 110 °C
Multi-step reaction with 4 steps 1: 80 percent / 3 h / Heating 2: 95 percent / electrolyte Bu4NBF4 / 1.13 h / 10 °C / Pt-anode 3: SnCl4 / H2O / 48 h / Ambient temperature 4: 12 N HCl, DOWEX 50(H+) / 24 h / 100 - 110 °C
Multi-step reaction with 4 steps 1: 88.5 percent / 2 h / Heating 2: 95 percent / Bu4NBF4 electrolyte / 0.8 h / 10 °C / Pt-anode 3: SnCl4 / H2O / 48 h / Ambient temperature 4: 12 N HCl, DOWEX 50(H+) / 24 h / 100 - 110 °C
  • 57
  • [ 534-00-9 ]
  • [ 1509-35-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 50 percent / various solvent(s) / 24 h / 85 °C 2: 90 percent / 1 N HCl / various solvent(s) 3: 69 percent / KOH 4: 84 percent / sat. Na2CO3 / diethyl ether / 0.5 h 5: 95 percent / electrolyte Bu4NBF4 / 1.13 h / 10 °C / Pt-anode 6: SnCl4 / H2O / 48 h / Ambient temperature 7: 12 N HCl, DOWEX 50(H+) / 24 h / 100 - 110 °C
Multi-step reaction with 7 steps 1: 50 percent / various solvent(s) / 24 h / 85 °C 2: 90 percent / 1 N HCl / various solvent(s) 3: 69 percent / KOH 4: 80 percent / 3 h / Heating 5: 95 percent / electrolyte Bu4NBF4 / 1.13 h / 10 °C / Pt-anode 6: SnCl4 / H2O / 48 h / Ambient temperature 7: 12 N HCl, DOWEX 50(H+) / 24 h / 100 - 110 °C
Multi-step reaction with 7 steps 1: 50 percent / various solvent(s) / 24 h / 85 °C 2: 90 percent / 1 N HCl / various solvent(s) 3: 69 percent / KOH 4: 88.5 percent / 2 h / Heating 5: 95 percent / Bu4NBF4 electrolyte / 0.8 h / 10 °C / Pt-anode 6: SnCl4 / H2O / 48 h / Ambient temperature 7: 12 N HCl, DOWEX 50(H+) / 24 h / 100 - 110 °C
  • 58
  • [ 38261-81-3 ]
  • [ 1509-35-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 93 percent / dimethylformamide / 2.5 h / 120 °C 2: 99 percent / hydrazine, HCl / ethanol / 4 h / Heating 3: 69 percent / KOH 4: 84 percent / sat. Na2CO3 / diethyl ether / 0.5 h 5: 95 percent / electrolyte Bu4NBF4 / 1.13 h / 10 °C / Pt-anode 6: SnCl4 / H2O / 48 h / Ambient temperature 7: 12 N HCl, DOWEX 50(H+) / 24 h / 100 - 110 °C
Multi-step reaction with 7 steps 1: 93 percent / dimethylformamide / 2.5 h / 120 °C 2: 99 percent / hydrazine, HCl / ethanol / 4 h / Heating 3: 69 percent / KOH 4: 80 percent / 3 h / Heating 5: 95 percent / electrolyte Bu4NBF4 / 1.13 h / 10 °C / Pt-anode 6: SnCl4 / H2O / 48 h / Ambient temperature 7: 12 N HCl, DOWEX 50(H+) / 24 h / 100 - 110 °C
Multi-step reaction with 7 steps 1: 93 percent / dimethylformamide / 2.5 h / 120 °C 2: 99 percent / hydrazine, HCl / ethanol / 4 h / Heating 3: 69 percent / KOH 4: 88.5 percent / 2 h / Heating 5: 95 percent / Bu4NBF4 electrolyte / 0.8 h / 10 °C / Pt-anode 6: SnCl4 / H2O / 48 h / Ambient temperature 7: 12 N HCl, DOWEX 50(H+) / 24 h / 100 - 110 °C
  • 59
  • [ 114284-81-0 ]
  • [ 1509-35-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 90 percent / 1 N HCl / various solvent(s) 2: 69 percent / KOH 3: 84 percent / sat. Na2CO3 / diethyl ether / 0.5 h 4: 95 percent / electrolyte Bu4NBF4 / 1.13 h / 10 °C / Pt-anode 5: SnCl4 / H2O / 48 h / Ambient temperature 6: 12 N HCl, DOWEX 50(H+) / 24 h / 100 - 110 °C
Multi-step reaction with 6 steps 1: 90 percent / 1 N HCl / various solvent(s) 2: 69 percent / KOH 3: 80 percent / 3 h / Heating 4: 95 percent / electrolyte Bu4NBF4 / 1.13 h / 10 °C / Pt-anode 5: SnCl4 / H2O / 48 h / Ambient temperature 6: 12 N HCl, DOWEX 50(H+) / 24 h / 100 - 110 °C
Multi-step reaction with 6 steps 1: 90 percent / 1 N HCl / various solvent(s) 2: 69 percent / KOH 3: 88.5 percent / 2 h / Heating 4: 95 percent / Bu4NBF4 electrolyte / 0.8 h / 10 °C / Pt-anode 5: SnCl4 / H2O / 48 h / Ambient temperature 6: 12 N HCl, DOWEX 50(H+) / 24 h / 100 - 110 °C
  • 60
  • (R)-2-(2-methyl-butyl)-isoindole-1,3-dione [ No CAS ]
  • [ 1509-35-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 99 percent / hydrazine, HCl / ethanol / 4 h / Heating 2: 69 percent / KOH 3: 84 percent / sat. Na2CO3 / diethyl ether / 0.5 h 4: 95 percent / electrolyte Bu4NBF4 / 1.13 h / 10 °C / Pt-anode 5: SnCl4 / H2O / 48 h / Ambient temperature 6: 12 N HCl, DOWEX 50(H+) / 24 h / 100 - 110 °C
Multi-step reaction with 6 steps 1: 99 percent / hydrazine, HCl / ethanol / 4 h / Heating 2: 69 percent / KOH 3: 80 percent / 3 h / Heating 4: 95 percent / electrolyte Bu4NBF4 / 1.13 h / 10 °C / Pt-anode 5: SnCl4 / H2O / 48 h / Ambient temperature 6: 12 N HCl, DOWEX 50(H+) / 24 h / 100 - 110 °C
Multi-step reaction with 6 steps 1: 99 percent / hydrazine, HCl / ethanol / 4 h / Heating 2: 69 percent / KOH 3: 88.5 percent / 2 h / Heating 4: 95 percent / Bu4NBF4 electrolyte / 0.8 h / 10 °C / Pt-anode 5: SnCl4 / H2O / 48 h / Ambient temperature 6: 12 N HCl, DOWEX 50(H+) / 24 h / 100 - 110 °C
  • 61
  • [ 106749-13-7 ]
  • [ 1509-35-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 67 percent / LDA, Me3SiCl, NBS 2: 93 percent / NaN3 / dimethylformamide / 60 h / Ambient temperature 3: 1.) Ti(OCH2Ph)4 2.) H2 / 2.) Pd/BaSO4 / 1.) benzyl alcohol, 130 gradC 2.) EtOH, EtOAc, 1 atm, r.t.
  • 62
  • [ 106749-11-5 ]
  • [ 1509-35-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / NaN3 / dimethylformamide / 60 h / Ambient temperature 2: 1.) Ti(OCH2Ph)4 2.) H2 / 2.) Pd/BaSO4 / 1.) benzyl alcohol, 130 gradC 2.) EtOH, EtOAc, 1 atm, r.t.
  • 63
  • [ 1509-35-9 ]
  • C70H110N5O18PSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1: triethylamine / tetrahydrofuran; H2O / 24 h / Ambient temperature 2: tetrahydrofuran / 1.5 h / Ambient temperature 3: 1.) LDA / 1.) THF, -78 deg C, 1 h 4: 83 percent / potassium borohydride / ethanol / 1.) 0 deg C, 1 h, 2.) RT, 24 h 5: 93 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C 6: hydrogen / 10percent Pd/C / methanol; ethyl acetate / 24 h / 40 Torr 7: 1.) N-methylmorpholine, isopropenyl chloroformate / 1.) THF, -15 deg C, 3 min, 2.)a) 0 deg C, 1 h, b) RT, 3 h 8: DMSO, trifluoroacetic acid, triethylamine / CH2Cl2 / 1.) from -78 deg C to RT, 1.5 h, 2.) RT, 1 h 9: NaH2PO4, KMnO4 / 2-methyl-propan-2-ol / 0.5 h 10: hydrogen / 10percent Pd/C / methanol; ethyl acetate / 24 h / 2068.6 Torr 11: NaHCO3 / dimethylformamide / 72 h / 0 °C
  • 64
  • [ 1509-35-9 ]
  • [ 126587-54-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran; H2O / 24 h / Ambient temperature 2: tetrahydrofuran / 1.5 h / Ambient temperature
  • 65
  • [ 1509-35-9 ]
  • [ 126587-57-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: triethylamine / tetrahydrofuran; H2O / 24 h / Ambient temperature 2: tetrahydrofuran / 1.5 h / Ambient temperature 3: 1.) LDA / 1.) THF, -78 deg C, 1 h 4: 83 percent / potassium borohydride / ethanol / 1.) 0 deg C, 1 h, 2.) RT, 24 h 5: 93 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C 6: hydrogen / 10percent Pd/C / methanol; ethyl acetate / 24 h / 40 Torr
  • 66
  • [ 1509-35-9 ]
  • [ 126587-70-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: triethylamine / tetrahydrofuran; H2O / 24 h / Ambient temperature 2: tetrahydrofuran / 1.5 h / Ambient temperature 3: 1.) LDA / 1.) THF, -78 deg C, 1 h 4: 83 percent / potassium borohydride / ethanol / 1.) 0 deg C, 1 h, 2.) RT, 24 h
  • 67
  • [ 1509-35-9 ]
  • [ 126587-55-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine / tetrahydrofuran; H2O / 24 h / Ambient temperature 2: tetrahydrofuran / 1.5 h / Ambient temperature 3: 1.) LDA / 1.) THF, -78 deg C, 1 h
  • 68
  • [ 1509-35-9 ]
  • [ 148339-15-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1: triethylamine / tetrahydrofuran; H2O / 24 h / Ambient temperature 2: tetrahydrofuran / 1.5 h / Ambient temperature 3: 1.) LDA / 1.) THF, -78 deg C, 1 h 4: 83 percent / potassium borohydride / ethanol / 1.) 0 deg C, 1 h, 2.) RT, 24 h 5: 93 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C 6: hydrogen / 10percent Pd/C / methanol; ethyl acetate / 24 h / 40 Torr 7: 1.) N-methylmorpholine, isopropenyl chloroformate / 1.) THF, -15 deg C, 3 min, 2.)a) 0 deg C, 1 h, b) RT, 3 h 8: DMSO, trifluoroacetic acid, triethylamine / CH2Cl2 / 1.) from -78 deg C to RT, 1.5 h, 2.) RT, 1 h 9: NaH2PO4, KMnO4 / 2-methyl-propan-2-ol / 0.5 h 10: hydrogen / 10percent Pd/C / methanol; ethyl acetate / 24 h / 2068.6 Torr
  • 69
  • [ 1509-35-9 ]
  • [ 126587-63-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: triethylamine / tetrahydrofuran; H2O / 24 h / Ambient temperature 2: tetrahydrofuran / 1.5 h / Ambient temperature 3: 1.) LDA / 1.) THF, -78 deg C, 1 h 4: 83 percent / potassium borohydride / ethanol / 1.) 0 deg C, 1 h, 2.) RT, 24 h 5: 93 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C 6: hydrogen / 10percent Pd/C / methanol; ethyl acetate / 24 h / 40 Torr 7: 1.) N-methylmorpholine, isopropenyl chloroformate / 1.) THF, -15 deg C, 3 min, 2.)a) 0 deg C, 1 h, b) RT, 3 h 8: 83 percent / HOAc, H2O / tetrahydrofuran / 12 h
  • 70
  • [ 1509-35-9 ]
  • [ 1053630-19-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: triethylamine / tetrahydrofuran; H2O / 24 h / Ambient temperature 2: tetrahydrofuran / 1.5 h / Ambient temperature 3: 1.) LDA / 1.) THF, -78 deg C, 1 h 4: 83 percent / potassium borohydride / ethanol / 1.) 0 deg C, 1 h, 2.) RT, 24 h 5: 93 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C 6: hydrogen / 10percent Pd/C / methanol; ethyl acetate / 24 h / 40 Torr 7: 1.) N-methylmorpholine, isopropenyl chloroformate / 1.) THF, -15 deg C, 3 min, 2.)a) 0 deg C, 1 h, b) RT, 3 h 8: DMSO, trifluoroacetic acid, triethylamine / CH2Cl2 / 1.) from -78 deg C to RT, 1.5 h, 2.) RT, 1 h
  • 71
  • [ 1509-35-9 ]
  • [ 126587-64-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: triethylamine / tetrahydrofuran; H2O / 24 h / Ambient temperature 2: tetrahydrofuran / 1.5 h / Ambient temperature 3: 1.) LDA / 1.) THF, -78 deg C, 1 h 4: 83 percent / potassium borohydride / ethanol / 1.) 0 deg C, 1 h, 2.) RT, 24 h 5: 93 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C 6: hydrogen / 10percent Pd/C / methanol; ethyl acetate / 24 h / 40 Torr 7: 1.) N-methylmorpholine, isopropenyl chloroformate / 1.) THF, -15 deg C, 3 min, 2.)a) 0 deg C, 1 h, b) RT, 3 h 8: DMSO, trifluoroacetic acid, triethylamine / CH2Cl2 / 1.) from -78 deg C to RT, 1.5 h, 2.) RT, 1 h 9: NaH2PO4, KMnO4 / 2-methyl-propan-2-ol / 0.5 h
  • 72
  • [ 1509-35-9 ]
  • [ 126587-62-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: triethylamine / tetrahydrofuran; H2O / 24 h / Ambient temperature 2: tetrahydrofuran / 1.5 h / Ambient temperature 3: 1.) LDA / 1.) THF, -78 deg C, 1 h 4: 83 percent / potassium borohydride / ethanol / 1.) 0 deg C, 1 h, 2.) RT, 24 h 5: 93 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C 6: hydrogen / 10percent Pd/C / methanol; ethyl acetate / 24 h / 40 Torr 7: 1.) N-methylmorpholine, isopropenyl chloroformate / 1.) THF, -15 deg C, 3 min, 2.)a) 0 deg C, 1 h, b) RT, 3 h
  • 73
  • [ 1509-35-9 ]
  • [ 130008-94-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: triethylamine / tetrahydrofuran; H2O / 24 h / Ambient temperature 2: tetrahydrofuran / 1.5 h / Ambient temperature 3: 1.) LDA / 1.) THF, -78 deg C, 1 h 4: 83 percent / potassium borohydride / ethanol / 1.) 0 deg C, 1 h, 2.) RT, 24 h 5: 7 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C
  • 74
  • [ 1509-35-9 ]
  • [ 129919-83-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: triethylamine / tetrahydrofuran; H2O / 24 h / Ambient temperature 2: tetrahydrofuran / 1.5 h / Ambient temperature 3: 1.) LDA / 1.) THF, -78 deg C, 1 h 4: 83 percent / potassium borohydride / ethanol / 1.) 0 deg C, 1 h, 2.) RT, 24 h 5: 93 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C
  • 75
  • [ 67-63-0 ]
  • [ 1509-35-9 ]
YieldReaction ConditionsOperation in experiment
In water A.5 Example A-5 80.0 g (163 mmol) of the complex obtained by the above procedures was put in a mixture of 720 mL of 2-propanol and 80 mL of water. The mixture was heated under reflux for 1 hour, and after cooling, solid substance was separated from the mixture at 25° C. The solid was rinsed three times with 80 mL each of 2-propanol and dried. Thus, 19.0 g of D-alloisoleucine was obtained as white crystal. Yield (based on the complex): 89.0%, Optical Purity: 99.9% de. The above washing was combined with the filtrate solution, and the combined liquor was heated to distill off 2-propanol. 100 mL of methanol was added to the concentrated residue to form a solution, which contained about 58 g of (2S,3S)-DBTA together with a small amount of isoleucine, which could be used for the subsequent cycle of optical resolution.
  • 76
  • 35%-hydrochloric acid [ No CAS ]
  • [ 67-63-0 ]
  • [ 1509-35-9 ]
YieldReaction ConditionsOperation in experiment
In water A.2 Example A-2 Example A-2 5 g (38.1 mmol) of the epimer mixture the same as used in Example A-1 was suspended in 49 ML of water in a reaction vessel, to which 1.98 g (19.1 mmol) of 35%-hydrochloric acid was added. Then, analogous to Example 1, 6.83 g (19.1 mmol) of (2S,3S)-DBTA was added to the suspension, and the mixture was heated to 70° C. and maintained at this temperature for 1 hour under stirring. The same treatment as in Example 1 gave 8.21 g of 1:1-complex of D-alloisoleucine with (2S,3S)-DBTA in the form of white crystal. The yield (based on the epimer mixture) was 44.0%, and the optical purity, 96.2% de. 8.0 g of this complex was put in a mixture of 72 mL of 2-propanol and 8 mL of water to decompose the complex as done in Example 1. D-alloisoleucine thus obtained weighed 1.90 g. The yield (based on the complex) was 88.4%, and the optical purity (HPLC), 100% de.
  • 77
  • [ 1509-35-9 ]
  • C23H42O5Si [ No CAS ]
  • C24H45NO4Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In tetrahydrofuran; water at 20℃;
  • 78
  • [ 1509-35-9 ]
  • N-(5-fluoro-2,4-dinitrophenyl)-L-leucinamide [ No CAS ]
  • [ 199729-64-1 ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate In acetone at 40℃; for 1h;
With sodium hydrogencarbonate In water; acetone at 37℃; for 1h;
  • 79
  • [ 1509-35-9 ]
  • N-(2,4-dinitro-5-fluorophenyl)-L-alaninamide [ No CAS ]
  • L-FDAA-D-allo-isoleucine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate In acetone at 40℃; for 1.5h;
With sodium hydrogencarbonate In water; acetone at 45℃; for 1h;
With sodium hydrogencarbonate In acetone at 40℃; for 90h; General procedure: Each amino acid was added with 0.1% solution of Nα-(5-fluoro-2,4-dinitrophenyl)-l-alaninamide (l-FDAA, Marfey's reagent, 200 μL) in acetone and 0.5M NaHCO3 (100 μL) followed by heating at 40 °C for 90 min. After cooling to room temperature, the reaction mixture was neutralized with 2N HCl (25 μL) and diluted with MeOH (300 μL). The solution was subjected to reversed-phase HPLC [Cosmosil 5C18-AR-II (4.6×250 mm), MeOH/20 mM AcONa=55:45 (solvent A) or 45:55 (solvent B) at 1.0 mL/min, UV detection at 340 nm].
With triethylamine In acetone; acetonitrile at 50℃; for 1.5h;
With sodium hydrogencarbonate In water; acetone at 43℃; for 2h; Marfey¢s or C3-Marfey¢s Analysis General procedure: The dried hydrolysate was dissolved in 120 μL water and then NaHCO3 (1 M, 20 μL) and 1% FDAA in acetone (400 μL) were added to the solution of the hydrolysate. The mixture was stirred at 43°C for 2 h and the reaction was terminated by an addition of 20 μL of 1 N HCl. The reaction mixture was diluted with 500 μL acetone to give amino acid-FDAA derivatives for the HPLC analysis. Each standard amino acid (1 mg) of L-isoleucine, D-isoleucine, L-isoleucine, L-allo-isoleucine, D-allo-isoleucine, L-leucine, D-leucine, L-methionine, D-methionine, L-phenylalanine, D-phenylalanine, L-proline, D-proline, L-valine, and D-valine was also converted to its FDAA derivatives.

  • 80
  • [ 1509-35-9 ]
  • [ 1228666-48-5 ]
  • [ 1258066-66-8 ]
YieldReaction ConditionsOperation in experiment
Stage #1: D-alloisoleucine; 1-tert-butyl 3-methyl 4-formyl-1H-pyrrolo[2,3-b]pyridine-1,3-dicarboxylate With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 2h; Stage #2: With methanol In dichloromethane 24.A EXAMPLE 24: (2i?,35)-N-cyclopentyl-3-methyl-2-(3-oxopyrrolo[4,3,2- de] [2,6]naphthyridin-4( l/f,3/f,5H)-yl)pentanamide[0269] STEP A: (2i?,35)-2-((l-(fert-butoxycarbonyl)-3-(methoxycarbonyl)-l/f- pyrrolo [2,3 -δ]pyridin-4-yl)methylamino)-3 -methylpentanoic acid[0270] To a 10 mL round bottom flask was added sodium triacetoxyborohydride (104 mg, 0.493 mmol), (2i?,35)-2-amino-3-methylpentanoic acid (43.1 mg, 0.329 mmol), and DCM (2 mL). The mixture was stirred at room temperature for 30 min, after which was added -tert-hvXy 3-methyl 4-formyl-lH-pyrrolo[2,3-δ]pyridine-l,3-dicarboxylate (50 mg, 0.164 mmol) in DCM (2 mL). The reaction was stirred at room temperature for 2 h and then quenched with MeOH (3 drops). The mixture concentrated to afford the title compound, which was used in the next step without further purification. [M+H] calc'd for C2IH29N3O6, 420; found, 420.6.
  • 81
  • [ 1509-35-9 ]
  • [ 113956-82-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sulfuric acid; sodium nitrite / water / 27 h / 20 °C / Cooling with ice 2.1: toluene-4-sulfonic acid / benzene / 0.5 h / Reflux 2.2: Reflux
Multi-step reaction with 2 steps 1: sulfuric acid; sodium nitrite / water / 19.25 h / 0 - 20 °C / Inert atmosphere; Schlenk technique 2: caesium carbonate / N,N-dimethyl-formamide / 20 h / 0 - 20 °C / Inert atmosphere; Schlenk technique
Multi-step reaction with 2 steps 1.1: sulfuric acid / 0.25 h / 0 °C 1.2: 18 h / 0 - 20 °C 2.1: potassium carbonate / N,N-dimethyl-formamide / 0 - 20 °C
  • 82
  • [ 1509-35-9 ]
  • [ 1093971-81-3 ]
  • C18H31NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% Stage #1: 2-((1R,2S,3R)-3-((triethylsilyl)oxy)-2-((Z)-pent-2-en-1-yl)cyclopentyl)acetic acid With triethylamine; isobutyl chloroformate In tetrahydrofuran; water at 20℃; for 3h; Stage #2: D-alloisoleucine With triethylamine In tetrahydrofuran at 20℃; for 48h; Stage #3: With formic acid at 0℃; for 0.5h;
  • 83
  • [ 328-50-7 ]
  • [ 1509-35-9 ]
  • 3-methyl-2-oxopentanoic acid [ No CAS ]
  • [ 6893-26-1 ]
YieldReaction ConditionsOperation in experiment
With pyridoxal 5'-phosphate; recombinant Lactobacillus salivarius UCC118 D-amino acid aminotransferase In aq. phosphate buffer at 30℃; for 0.0166667h; Enzymatic reaction; General procedure: Amino donor specificity was determined using UPLC by measuring the rate of D-glutamate formation from α-ketoglutarate in the presence of various D-amino acids. The standard reaction mixture (1 ml) contained 100 mM potassium phosphate buffer (pH 7.5), 50 mM D-amino acid, 20 mM α-ketoglutarate, 0.05 mM pyridoxal-5′-phosphate (PLP) and the purified D-AAT. The enzyme reaction was run at 30 °C for 1 min and was stopped by adding 1 ml of 20% trichloroacetic acid. The reaction mixture was then incubated for 1 min on ice and 0.5 ml of 4 M NaOH was added to neutralize the mixture. UPLC analysis was performed using an ACQUITY UPLC TUV system consisting of a Waters Binary Solvent Manager, Sample Manager, FLR Detector and AccQ-Tag Ultra 2.1 × 100-mm column (Waters, Tokyo, Japan) with an eluent flow rate of 0.25 ml/min [14]. The column temperature was 30 °C, and the fluorescent wavelengths used for the FLR Detector were 350 and 450 nm. The eluent was linearly graduated using 85% 50 mM sodium acetate buffer (pH 5.9) and 15% acetonitrile.
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