[ CAS No. 17407-55-5 ] {[proInfo.proName]}

Name: 17407-55-5|(S)-2-Hydroxy-3-methylbutanoic acid|97%
Brand: Ambeed
SKU: A166929
Price: 5.0 USD
Availability: InStock
Rating: 95 (25 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

DV 2D 3D

3d Animation Molecule Structure of 17407-55-5

Structure of 17407-55-5 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 17407-55-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 17407-55-5 ]

SDS Specification

Alternatived Products of [ 17407-55-5 ]

Product Details of [ 17407-55-5 ]

CAS No. :	17407-55-5	MDL No. :	MFCD00066443
Formula :	C₅H₁₀O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NGEWQZIDQIYUNV-BYPYZUCNSA-N
M.W :	118.13	Pubchem ID :	853180
Synonyms :

Calculated chemistry of [ 17407-55-5 ]

Physicochemical Properties

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

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) :	-6.67 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.97
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

Druglikeness

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

Water Solubility

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

Medicinal Chemistry

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

Safety of [ 17407-55-5 ]

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:

Application In Synthesis of [ 17407-55-5 ]

* 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.

Upstream synthesis route of [ 17407-55-5 ]
Downstream synthetic route of [ 17407-55-5 ]

[ 17407-55-5 ] Synthesis Path-Upstream 1~8

1
[ 17407-55-5 ]
[ 200731-31-3 ]
[ 39968-33-7 ]

Yield	Reaction Conditions	Operation in experiment
88%	With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16 h;	Step 6 To a mixture of the product of step 5, Example 50, (0.50 g, 0.872 mmol), DIPEA (1.29 g, 11.5 mmol), and (S)-(+)-α-hydroxy-3-methylbutyric acid (0.156 g, 1.13 mmol) in CH₂Cl₂(9 mL) was added HATU (0.597 g, 1.57 mmol). After stirring at ambient temperature for 16 h, the white precipitate byproduct HOAT was removed by vaccum filtrarion and washed with EtOAc (25 mL). The liquid filtrate was concentrated and the resulting residue was redissolved in EtOAc (75 mL) and washed with 2.x.10 mL 0.1 aqueous HCl. The aqueous layers were combined and extracted with EtOAc (50 mL). The organic layer was washed with 10percent Na₂CO₃(aq), brine, dried over MgSO₄, and filtered. The filtrate was concentrated in vacuo to dryness. The residue was purified by flash column chromatography (SiO₂, 97:3, DCM:MeOH) to yield 0.436 g (88percent) of Compound 50 as a white foamy solid. ¹H NMR (CD₃OD) δ ppm 0.93 (d, J=6.72 Hz, 3H), 1.00 (d, J=6.72 Hz, 3H), 1.10 (dd, J=7.9, 2.4 Hz, 2H), 1.23-1.30 (m, 2H), 1.45 (dd, J=9.3, 5.4 Hz, 1H), 1.93 (dd, J=9.3, 5.4 Hz, 1H), 2.06-2.12 (m, 1H), 2.28 (q, J=8.9 Hz, 1H), 2.37-2.43 (m, 1H), 2.69 (dd, J=13.7, 6.4 Hz, 1H), 2.94-2.99 (m, 1H), 4.08 (d, J=5.5 Hz, 1H), 4.11 (dd, J=12.5, 3.5 Hz, 1H), 4.32 (d, J=12.5 Hz, 1H), 4.65 (dd, J=10.1, 7.0 Hz, 1H), 5.16 (dd, J=10.4, 1.5 Hz, 1H), 5.34 (dd, J=17.2, 1.4 Hz, 1H), 5.76-5.83 (m, 1H), 5.91 (br s, 1H), 7.33 (dd, J=9.2, 2.4 Hz, 1H), 7.37 (d, J=2.5 Hz, 1H), 7.50 (d, J=6.1 Hz, 1H), 7.92 (d, J=6.4 Hz, 1H), 8.22 (d, J=9.2 Hz, 1H); LC-MS, MS m/z 601 (M⁺+H).

Reference： [1] Patent: US2006/183694, 2006, A1, . Location in patent: Page/Page column 47-48

2
[ 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, # 10, p. 2137 - 2142

3
[ 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, # 10, p. 2137 - 2142

4
[ 17407-55-5 ]
[ 7146-15-8 ]

Reference： [1] Heterocycles, 2000, vol. 52, # 1, p. 151 - 158

5
[ 67-56-1 ]
[ 17407-55-5 ]
[ 24347-63-5 ]

Yield	Reaction Conditions	Operation in experiment
82%	With toluene-4-sulfonic acid In tetrachloromethane at 20℃; for 10 h;	Methanol (14.5 mL, 360 mmol) and p-TsOH*H₂O (0.68 g, 3.6 mmol) were added to a solution of (S)-valinic acid^14a 5 (14.20 g, 120 mmol) in CCl₄ (40 mL). The resulting mixture was refluxed for 10 h under anhydrous conditions. Next, the mixture was cooled to rt, washed with water (15 mL), saturated aqueous NaHCO₃ (10 mL), dried over MgSO₄ and concentrated under reduced pressure. The residue was distilled to give methyl ester 6 (13.03 g, 82percent) as a colourless oil; bp 62-63 °C/15 Torr; [α]_D = +23.7 (c 1.00, CHCl₃), lit.^14b [α]_D = +24.3 (c 1.00, CHCl₃); ¹H NMR (CDCl₃) d 0.82 (d, J = 6.9 Hz, 3H, 3-Me), 0.98 (d, J = 6.9 Hz, 3H, 3-Me), 2.03 (sept. of d, J = 6.9, 3.6 Hz, 1H, 3-H), 2.83 (d, J = 6.2 Hz, 1H, OH), 3.75 (s, 3H, CO₂Me), 4.01 (dd, J = 6.2, 3.6 Hz, 1H, 2-H); ¹³C NMR (CDCl₃) d 15.9, 18.6, 32.1, 52.2, 75.0, 175.3; IR (film) ν_max: 3483, 1735 cm^-1.

Reference： [1] Journal of the American Chemical Society, 1990, vol. 112, # 21, p. 7659 - 7672
[2] Tetrahedron Letters, 1989, vol. 30, # 29, p. 3757 - 3760
[3] Journal of Chemical Research, Miniprint, 1998, # 1, p. 126 - 142
[4] Heterocycles, 1999, vol. 51, # 6, p. 1321 - 1343
[5] Organic and Biomolecular Chemistry, 2005, vol. 3, # 20, p. 3749 - 3756
[6] Tetrahedron Asymmetry, 2011, vol. 22, # 13, p. 1448 - 1454
[7] Journal of Antibiotics, 2002, vol. 55, # 3, p. 322 - 336
[8] Journal of the Chemical Society - Perkin Transactions 1, 1996, # 12, p. 1427 - 1433
[9] Journal of Organic Chemistry, 1993, vol. 58, # 7, p. 1646 - 1648
[10] Chemische Berichte, 1994, vol. 127, # 10, p. 1969 - 1980
[11] Heterocycles, 2000, vol. 52, # 1, p. 151 - 158

6
[ 17407-55-5 ]
[ 77-76-9 ]
[ 24347-63-5 ]

Reference： [1] Patent: US2008/194672, 2008, A1, . Location in patent: Page/Page column 49-50
[2] Angewandte Chemie - International Edition, 2005, vol. 44, # 19, p. 2903 - 2907
[3] Patent: US2006/211630, 2006, A1, . Location in patent: Page/Page column 7
[4] Patent: US2009/163446, 2009, A1, . Location in patent: Page/Page column 26

7
[ 17407-55-5 ]
[ 74-88-4 ]
[ 24347-63-5 ]

Reference： [1] Journal of Organic Chemistry, 1997, vol. 62, # 7, p. 2292 - 2297
[2] Tetrahedron Letters, 2017, vol. 58, # 3, p. 185 - 189

8
[ 186581-53-3 ]
[ 17407-55-5 ]
[ 24347-63-5 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1983, vol. 2, # 7/8, p. 185 - 194
[2] Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 3, p. 1027 - 1036
[3] Tetrahedron, 1998, vol. 54, # 48, p. 14549 - 14564
[4] Tetrahedron, 1969, vol. 25, p. 2193 - 2221
[5] Tetrahedron Letters, 1987, vol. 28, # 10, p. 1019 - 1022
[6] Canadian Journal of Chemistry, 1989, vol. 67, # 6, p. 1065 - 1070
[7] European Journal of Organic Chemistry, 2012, # 27, p. 5141 - 5150
[8] Organic Letters, 2014, vol. 16, # 12, p. 3256 - 3259
[9] Journal of Natural Products, 2014, vol. 77, # 4, p. 969 - 975

[ 17407-55-5 ] Synthesis Path-Downstream 1~35

1
[ 72-18-4 ]
[ 17407-55-5 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sulfuric acid; NaNO₂ In water monomer
96%
91%	With sulfuric acid; water monomer; NaNO₂ at 60℃; Flow reactor;

80%	With sulfuric acid; NaNO₂
80%	With sulfuric acid; NaNO₂
79%	With sulfuric acid; NaNO₂ for 2h; Ambient temperature;
78%	With sulfuric acid; NaNO₂ at 0 - 20℃;
78%	With sulfuric acid; NaNO₂ at 0 - 20℃;
77%	With sulfuric acid; NaNO₂ In water monomer at 0 - 20℃; for 27h;
76%	With NaNO₂ In water monomer; acetic acid at 20℃; for 0.5h;
75%	With sulfuric acid; NaNO₂ In water monomer at 0℃; for 4h;
74%	With sulfuric acid; NaNO₂ In water monomer at 20℃; for 12h;
71%	Stage #1: L-valine With sulfuric acid; NaNO₂ Inert atmosphere; Stage #2: With sulfuric acid In methanol Inert atmosphere;
70%	With sulfuric acid; NaNO₂ at 0℃;
66%	With sulfuric acid; NaNO₂ In water monomer at 0℃; for 2h;
65%	With sulfuric acid; NaNO₂ In water monomer at 0 - 25℃;
60%	With sulfuric acid; NaNO₂ at 0 - 25℃; for 2h;
59%	With sulfuric acid; NaNO₂ In water monomer 1.) 0 deg C, 3 h, 2.) RT, 2 h;
58%	With NaNO₂ In sulfuric acid at 0℃; for 2h;
57%	With sulfuric acid; NaNO₂ In water monomer 1.) 0 deg C, 3 h, 2.) RT, 12 h;
57%	With sulfuric acid; NaNO₂
56%	With sulfuric acid; NaNO₂ In water monomer at -5 - 20℃;
56%	With sulfuric acid; water monomer; NaNO₂ at 5 - 20℃; Inert atmosphere;
53%	With sulfuric acid; water monomer; NaNO₂ at 20℃; for 10h; Cooling with ice;
52%	With sulfuric acid; NaNO₂ at 20℃; Schlenk technique; Inert atmosphere;
45%	With sulfuric acid; NaNO₂ for 24h; Ambient temperature;
41%	With sulfuric acid; NaNO₂ In water monomer at 20℃; for 24h;
35%	With cis-nitrous acid
35%	With sulfuric acid; NaNO₂ In water monomer
35%	With sulfuric acid; NaNO₂ In water monomer stereoselective reaction;
34%	With sulfuric acid; NaNO₂ at 25℃; for 2h;
31%	With sulfuric acid; NaNO₂ In water monomer at 0 - 20℃;
31%	With sulfuric acid; NaNO₂ In water monomer at 0 - 22℃; for 18h;
	With hydrogenchloride; silver(I) nitrite
	With sulfuric acid Diazotization;
	With hydrogenchloride; acetic acid; NaNO₂
	With sulfuric acid; NaNO₂
	With cis-nitrous acid
	With sulfuric acid; NaNO₂ In water monomer at 5℃; for 5h;
	With sulfuric acid; NaNO₂ In water monomer
	With sulfuric acid; NaNO₂ 1.) 0 deg C, 3 h, 2.) 0 deg C to RT, 15 h;
	With sulfuric acid; NaNO₂ In water monomer at 0℃;
	With cis-nitrous acid Yield given;
	With sulfuric acid; NaNO₂ at 20℃;
	With hydrogenchloride; NaNO₂ In water monomer at 0 - 20℃;
	With sulfuric acid; NaNO₂ In water monomer
	With sulfuric acid; NaNO₂ In water monomer at 0 - 20℃;
	With sulfuric acid; NaNO₂ In water monomer at 0℃; for 24h;
	Stage #1: L-valine With acetic acid; NaNO₂ In water monomer Stage #2: With potassium carbonate In methanol; water monomer
	With NaNO₂
	With sulfuric acid; NaNO₂ In water monomer at 0 - 20℃;
	With hydrogenchloride; NaNO₂ at 0℃; for 6h;
	Stage #1: L-valine With acetic acid; NaNO₂ In water monomer at -5 - 0℃; for 3h; Inert atmosphere; Stage #2: With hydrogenchloride; water monomer; methylamine Inert atmosphere;
	With sulfuric acid; NaNO₂ In water monomer at 0 - 5℃; for 24h;	2 To a solution of L-amino acid 1 (25.0 mmol) in H2SO4 2N (37.5 ml, aqueous solution), cooled to 0° C., was added a solution of NaNO2 2N (2.57 g, 37.0 mmol) in water (9 ml). The temperature was maintained below 5° C. during the addition, and the mixture was stirred at such a temperature for 24 h. The solution was saturated with (NH4)2SO4, extracted with ether (3x25 ml), dried over Na2SO4 and evaporated under reduced pressure giving 2.72 g (23.0 mmol) of the corresponding ?-hydroxy acid as an oil. A solution of this oily material, p-toluenesulfonic acid monohydrate (0.03 g, 0.16 mmol) and dimethoxypropane (2.8 ml, 23.0 mmol) in methanol (1.15 ml) was heated at 45° C. for 24 h. The reaction mixture was evaporated under reduced pressure providing the corresponding {overscore (?)}hydroxy methyl ester 2 as an oil. This material was dissolved in anhydrous tetrahydrofuran (40 ml) and anhydrous N,N-dimethylformamide (12 ml), under an inert atmosphere, was cooled to 0° C. NaH (0.48 g, 20.0 mmol) was added and the mixture was stirred for 10 min. The corresponding bromide 3 (24.0 mmol) was added dropwise, and the mixture was allowed to reach room temperature. The reaction was monitored by TLC. When the reaction was complete, the reaction mixture was diluted in ether (130 ml) and washed with water (3x50 ml). The remaining organic layer was dried over Na2SO4 and evaporated under reduced pressure, providing the crude product 4, which was purified by flash column chromatography. (S)-Methyl 2-(2-fluorobenzyloxy)-3-methylbutanoate. This compound was prepared from L-valine and 2-fluorobenzyl bromide in 40 % yield: bp 70-72° C. (0.5 mm Hg); IR 1751, 1229 cm-1; 1H-NMR (? ppm, CDCl3) 7.49-6.97 (m, 4H), 4.71 (d, 1H, J=12.1 Hz), 4.49 (d, 1H, J=12.1 Hz), 3.74 (s, 3H), 3.71 (d, 1H, J=5.7 Hz), 2.18-2.00 (m, 1H), 0.96 (d, 3H, J=4.0 Hz), 0.92 (d, 3H, J=4.0 Hz); 13C-NMR (? ppm, CDCl3) 172.8, 163.1, 158.2, 130.3, 130.2, 129.5, 129.4, 124.0, 123.9, 115.3, 114.9, 83.6, 66.1, 66.0, 51.7, 31.6, 18.7, 17.7; [?]D25=-64.9 (c=1.27, CH2Cl2).
	With sulfuric acid; NaNO₂
	With sulfuric acid; NaNO₂ In water monomer at 0 - 20℃; for 17h;	Methyl (2S)-2-hydroxy-3-methylbutanoate. A solution of sodium nitrite (4.30 g, 62.3 mmol) in water (17 mL) was added dropwise to a cooled (0 °C) solution of (S)-valine (5.00 g, 42.7 mmol) in 1 N sulfuric acid (68 mL) and was allowed to stir for 1 h. The mixture was then warmed to rt and allowed to stir for 16 h. The solution was then extracted with Et2O (6 x 80 mL) and the organic layers were combined, dried over MgSO4, filtered and then concentrated in vacuo. Crude compound was carried on to subsequent transformation [5]. (2S)-2-Hydroxy-3-methylbutanoic acid was dissolved in acetone (100 mL). K2CO3 (7.60 g, 55 mmol) was then added and the solution was allowed to stir at rt for 1 h. MeI (4.00 mL, 64 mmol) was then added and the solution was heated to reflux for 20 h. The reaction was then allowed to cool to rt and then filtered and concentrated in vacuo. The crude material was distilled at 72 °C at 23 torr to give a clear, colorless oil. Spectroscopic data is identical to that previously reported [6].
	With sulfuric acid; water monomer; NaNO₂ at 0 - 20℃; for 1h;	1.1 1. (S)-2-hydroxy-3-methylbutanoic acid (step 1) (5.9 g, 85.2 mmol) was slowly added to a cold solution of L-valine acid (5.0 g (g), 42.7 mmol (mmol)) in 2N sulfuric acid (60 mL (ml) In the water (30 mL) solution, while the addition temperature should be maintained at 0 ° C. The solution was stirred at 0 ° C for 1 hour and stirred at room temperature until the starting material showed complete conversion of the amino acid in TLC. The reaction mixture was extracted with ethyl acetate (4 x 30 mL) and the organic layer was combined, dried over MgSO4 and concentrated in vacuo to give 4.5 g of a colorless liquid which was used directly in the next step without further purification.
	With sulfuric acid; water monomer; NaNO₂ at 0 - 5℃; for 2.5h;	1 Example 1: Preparation of compound of formula (3) L-valine (100 g) is suspended in water (300 mL) and cooled to 3-5° C. 2 M sulfuric acid aqueous solution (640 mL) was slowly added dropwise while maintaining the solution at 3-5° c. Sodium nitrite (176.7 g) was added to water (500 mL) to 5°c for 1.5 hours, and the reaction mixture was maintained at 0-5°c for 1 hour. The progress of the reaction was observed by thin layer chromatography (hexane: ethyl acetate: acetic acid = 5: 1: 0.1). After completion of the reaction, the pH of the reaction solution was adjusted to 1-2 and n-butanol (500 mL) was added thereto. The organic layer was separated and the water layer was extracted with n-butanol (250 mL × 1 times, 125 mL × 1 times). The-2-hydroxy-3-methylbutanoic acid dissolved in n-butanol was used in a next step reaction without a concentration process
	With sulfuric acid; NaNO₂ In water monomer at 0 - 20℃; for 6h; Inert atmosphere;
	With sulfuric acid; NaNO₂ In water monomer at 20℃; Cooling with ice;	Procedure for Step J To a solution of acid amino acid in 1N H2SO4, a solution of NaNO2 in minimal quantity of water was added under cooling. The resulted mixture was stirred at room temperature for 1-3 days, saturated with Na2SO4, and extracted with a solvent like methyl-tert-butyl ether or DCM. The organic layer was evaporated
	With sulfuric acid; NaNO₂ at 0 - 20℃;
	With sulfuric acid; NaNO₂ In water monomer at 0 - 20℃; for 15h;
	With sulfuric acid; NaNO₂ In water monomer at 0 - 20℃; for 22.5h;

Reference： [1]Honda, Yutaka; Ori, Aiichiro; Tsuchihashi, Gen-ichi [Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 3, p. 1027 - 1036]
[2]Location in patent: scheme or table Shklyaruck, Denis; Matiushenkov, Evgenii [Tetrahedron Asymmetry, 2011, vol. 22, # 13, p. 1448 - 1454]
[3]Hu, Dennis X.; O'Brien, Matthew; Ley, Steven V. [Organic Letters, 2012, vol. 14, # 16, p. 4246 - 4249]
[4]Brungs; Danielmeier; Jakobi; Nothhelfer; Stahl; Zietlow; Steckhan [Journal de Chimie Physique et de Physico-Chimie Biologique, 1996, vol. 93, # 4, p. 575 - 590]
[5]Joullie; Portonovo; Liang; Richard [Tetrahedron Letters, 2000, vol. 41, # 49, p. 9373 - 9376]
[6]Kim, Hwa-Ok; Olsen, Richard K.; Choi, Ok-Soon [Journal of Organic Chemistry, 1987, vol. 52, # 20, p. 4531 - 4536]
[7]Liang; Richard; Portonovo; Joullie [Journal of the American Chemical Society, 2001, vol. 123, # 19, p. 4469 - 4474]
[8]Liang; Richard; Portonovo; Joullie [Journal of the American Chemical Society, 2001, vol. 123, # 19, p. 4469 - 4474]
[9]Casalme, Loida O.; Yamauchi, Arisa; Sato, Akinori; Petitbois, Julie G.; Nogata, Yasuyuki; Yoshimura, Erina; Okino, Tatsufumi; Umezawa, Taiki; Matsuda, Fuyuhiko [Organic and Biomolecular Chemistry, 2017, vol. 15, # 5, p. 1140 - 1150]
[10]Horikawa, Eiji; Kodaka, Masato; Nakahara, Yoshiaki; Okuno, Hiroaki; Nakamura, Kazuhiko [Tetrahedron Letters, 2001, vol. 42, # 47, p. 8337 - 8339]
[11]Horn, Alexander; Kazmaier, Uli [Organic Letters, 2019, vol. 21, # 12, p. 4595 - 4599]
[12]Li, Maosheng; Tang, Jiadong; Tao, Youhua; Wang, Xianhong [Angewandte Chemie - International Edition, 2022, vol. 61, # 15][Angew. Chem., 2022, vol. 134, # 15]
[13]Izgu, Enver Cagri; Burns, Aaron C.; Hoye, Thomas R. [Organic Letters, 2011, vol. 13, # 4, p. 703 - 705]
[14]Anand, Ramesh C.; Selvapalam, N. [Journal of Chemical Research, Miniprint, 1998, # 1, p. 126 - 142]
[15]Guyon, Hélène; Boussonnière, Anne; Castanet, Anne-Sophie [Journal of Organic Chemistry, 2017, vol. 82, # 9, p. 4949 - 4957]
[16]Shrestha, Bijay; Rose, Brennan T.; Olen, Casey L.; Roth, Aaron; Kwong, Adon C.; Wang, Yang; Denmark, Scott E. [Journal of Organic Chemistry, 2021, vol. 86, # 4, p. 3490 - 3534]
[17]Moriarty, Robert M.; Enache, Livia A.; Kinney, William A.; Allen, Craig S.; Canary, James W.; et al. [Tetrahedron Letters, 1995, vol. 36, # 29, p. 5139 - 5142]
[18]Johnson, Rodney L. [Journal of Medicinal Chemistry, 1980, vol. 23, # 6, p. 666 - 669]
[19]Koch, Patrick; Nakatani, Yoichi; Luu, Bang; Ourisson, Guy [Bulletin de la Societe Chimique de France, 1983, vol. 2, # 7/8, p. 185 - 194]
[20]Li; Ewing; Harris; Joullie [Journal of the American Chemical Society, 1990, vol. 112, # 21, p. 7659 - 7672]
[21]Ewing, William R.; Harris, Bruce D.; Li, Wen-Ren; Joullie, Madeleine M. [Tetrahedron Letters, 1989, vol. 30, # 29, p. 3757 - 3760]
[22]Current Patent Assignee: SANOFI - US6359012, 2002, B1 Location in patent: Example 1
[23]Coutts, Lisa D.; Geiss, William B.; Gregg, Brian T.; Helle, Mark A.; King, Chi-Hsin R.; Itov, Zinovy; Mateo, Mary E.; Meckler, Harold; Zettler, Mark W.; Knutson, Joyce C. [Organic Process Research and Development, 2002, vol. 6, # 3, p. 246 - 255]
[24]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]
[25]Maron, Eva; Swisher, Jordan H.; Haven, Joris J.; Meyer, Tara Y.; Junkers, Tanja; Börner, Hans G. [Angewandte Chemie - International Edition, 2019, vol. 58, # 31, p. 10747 - 10751][Angew. Chem., 2019, vol. 131, # 31, p. 10858 - 10863,6]
[26]Gonzalez, Isabel; Jou, Gemma; Caba, Josep Maria; Albericio, Fernando; Lloyd-Williams, Paul; Giralt, Ernest [Journal of the Chemical Society. Perkin transactions I, 1996, # 12, p. 1427 - 1433]
[27]Hasuoka, Atsushi; Nishikimi, Yuji; Nakayama, Yutaka; Kamiyama, Keiji; Nakao, Masafumi; Miyagawa, Ken-Ichiro; Nishimura, Osamu; Fujino, Masahiko [Journal of Antibiotics, 2002, vol. 55, # 3, p. 322 - 336]
[28]Rebiere, F.; Riant, O.; Kagan, H.B. [Tetrahedron Asymmetry, 1990, vol. 1, # 3, p. 199 - 214]
[29]Stavrakov, Georgi; Valcheva, Violeta; Philipova, Irena; Doytchinova, Irini [European Journal of Medicinal Chemistry, 2013, vol. 70, p. 372 - 379]
[30]Stavrakov, Georgi; Philipova, Irena; Valcheva, Violeta; Momekov, Georgi [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 1, p. 165 - 167]
[31]Burgess, Kevin [Tetrahedron Letters, 1995, vol. 36, # 16, p. 2725 - 2728]
[32]Bauer, Tomasz; Gajewiak, Joanna [Tetrahedron, 2004, vol. 60, # 41, p. 9163 - 9170]
[33]Anderson, Zoe J.; Fox, David J. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 4, p. 1450 - 1454]
[34]Baker; Meister [Journal of the American Chemical Society, 1951, vol. 73, p. 1336]
[35]Cook; Cox; Farmer [Journal of the Chemical Society, 1949, p. 1027] Bartlett; Kuna; Levene [Journal of Biological Chemistry, 1937, vol. 118, p. 515]
[36]Winitz et al. [Journal of the American Chemical Society, 1956, vol. 78, p. 2423,2428]
[37]Losse,G.; Bachmann,G. [Chemische Berichte, 1964, vol. 97, p. 2671 - 2680]
[38]Tatsumi,S. et al. [Bulletin of the Chemical Society of Japan, 1964, vol. 37, p. 846 - 849]
[39]Koppenhoefer, B.; Trettin, U.; Figura, R.; Lin, B. [Tetrahedron Letters, 1989, vol. 30, # 38, p. 5109 - 5110]
[40]Mead, Keith T. [Tetrahedron Letters, 1987, vol. 28, # 10, p. 1019 - 1022]
[41]Palomo, Claudio; Aizpurua, Jesus M.; Urchegui, Raquel; Garcia, Jesus M. [Journal of Organic Chemistry, 1993, vol. 58, # 7, p. 1646 - 1648]
[42]Cahiez, Gerard; Metais, Eric [Tetrahedron Letters, 1995, vol. 36, # 36, p. 6449 - 6452]
[43]Girreser; Noe [Synthesis, 1995, # 10, p. 1223 - 1224]
[44]James, David G.; Moore, Christopher J.; Aldrich, Jeffrey R. [Journal of Chemical Ecology, 1994, vol. 20, # 12, p. 3281 - 3296]
[45]Suzuki; Ojika; Sakagai; Kaida; Fudou; Kameyama [Journal of Antibiotics, 2001, vol. 54, # 1, p. 22 - 28]
[46]Xu, Zhengshuang; Peng, Yungui; Ye, Tao [Organic Letters, 2003, vol. 5, # 16, p. 2821 - 2824]
[47]Peng, Yungui; Pang, Heung Wing; Ye, Tao [Organic Letters, 2004, vol. 6, # 21, p. 3781 - 3784]
[48]Zubia, Aizpea; Mendoza, Lorea; Vivanco, Silvia; Aldaba, Eneko; Carrascal, Teresa; Lecea, Begona; Arrieta, Ana; Zimmerman, Tahl; Vidal-Vanaclocha, Fernando; Cossio, Fernando P. [Angewandte Chemie - International Edition, 2005, vol. 44, # 19, p. 2903 - 2907]
[49]Uesusuki, Shinya; Watanabe, Bunta; Yamamoto, Shuji; Otsuki, Junko; Nakagawa, Yoshiaki; Miyagawa, Hisashi [Bioscience, Biotechnology and Biochemistry, 2004, vol. 68, # 5, p. 1097 - 1105]
[50]Vigneron,J.P. et al. [Tetrahedron, 1977, vol. 33, p. 507 - 510]
[51]Shin; Lee; Lee; Jung; Lee; Yoon [Journal of Organic Chemistry, 2000, vol. 65, # 22, p. 7667 - 7675]
[52]Yang; Li; Ng; Yan; Qu; Wu [Journal of Organic Chemistry, 2001, vol. 66, # 22, p. 7303 - 7312]
[53]Studte, Christopher; Breit, Bernhard [Angewandte Chemie - International Edition, 2008, vol. 47, # 29, p. 5451 - 5455]
[54]Current Patent Assignee: UNIVERSITY OF THE BASQUE COUNTRY; DOMINION PHARMAKINE S L - US2006/211630, 2006, A1 Location in patent: Page/Page column 7
[55]Location in patent: scheme or table Horton, Alexandra E.; May, Oliver S.; Elsegood, Mark R. J.; Kimber, Marc C. [Synlett, 2011, # 6, p. 797 - 800]
[56]Alfie, Rachel J.; Truong, Ngoc; Yost, Julianne M.; Coltart, Don M. [Tetrahedron Letters, 2017, vol. 58, # 3, p. 185 - 189]
[57]Current Patent Assignee: NATIONAL YANG MING CHIAO TUNG UNIVERSITY - TWI543759, 2016, B Location in patent: Page/Page column 12; 13
[58]Current Patent Assignee: YONSUNG FINE CHEMICAL CO LTD - KR2018/116959, 2018, A Location in patent: Paragraph 0122; 0221; 0222
[59]Fernandes, Alessandra A. G.; Leonarczyk, Ives A.; Ferreira, Marco A. B.; Dias, Luiz Carlos [Organic and Biomolecular Chemistry, 2019, vol. 17, # 12, p. 3167 - 3180]
[60]Current Patent Assignee: NMD PHARMA AS - US2019/185409, 2019, A1 Location in patent: Paragraph 1152; 1153
[61]Mills, Jonathan J.; Pierce, Joshua G.; Robinson, Kaylib R. [ACS Medicinal Chemistry Letters, 2019, vol. 10, # 3, p. 374 - 377]
[62]Lee, Seung Jong; Moon, Hyung Wook; Lee, Kee-Young; Oh, Chang Young; Kim, U Bin; Shin, Hyunik [Organic Process Research and Development, 2021, vol. 25, # 4, p. 982 - 987]
[63]Hernández-Ruiz, Raquel; Rubio-Presa, Rubén; Suárez-Pantiga, Samuel; Pedrosa, María R.; Fernández-Rodríguez, Manuel A.; Tapia, M. José; Sanz, Roberto [Chemistry - A European Journal, 2021, vol. 27, # 54, p. 13613 - 13623]

2
[ 4026-18-0 ]
[ 17407-55-5 ]

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

3
[ 186581-53-3 ]
[ 17407-55-5 ]
[ 24347-63-5 ]

Reference： [1]Bulletin de la Societe Chimique de France,1983,vol. 2,p. 185 - 194
[2]Bulletin of the Chemical Society of Japan,1987,vol. 60,p. 1027 - 1036
[3]Tetrahedron,1998,vol. 54,p. 14549 - 14564
[4]Tetrahedron,1969,vol. 25,p. 2193 - 2221
[5]Canadian Journal of Chemistry,1989,vol. 67,p. 1065 - 1070
[6]European Journal of Organic Chemistry,2012,p. 5141 - 5150
[7]Organic Letters,2014,vol. 16,p. 3256 - 3259
[8]Journal of Natural Products,2014,vol. 77,p. 969 - 975

4
[ 67-56-1 ]
[ 17407-55-5 ]
[ 24347-63-5 ]

Yield	Reaction Conditions	Operation in experiment
91%	With sulfuric acid; at 20℃; for 4h;Reflux;	To a solution of (S)-2-hydroxy-3-methylbutanoic acid (4.l4g, 35 mmol) in MeOH (50 mL) was added H2S04 (2.0 mL) at room temperature in portions. The reaction was refluxed for 4 hours. The reaction solution was cooled to room temperature and concentrated in vacuo. The residue was diluted with DCM (50 mL), washed with sat. aq. Na2C03 and brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give the desired product l,3-dibromo-2-(bromomethyl)benzene as a pale orange oil (4.21 g). Yield 91%. 1H NMR (400 MHz, CDC13) d 4.06 (m, 1H), 3.81 (s, 3H), 2.68 (m, 1H), 2.08 (m,lH), l.03(d, J=6.8Hz, 3H), 0.87(d, J=6.8Hz, 3H).
82%	With toluene-4-sulfonic acid; In tetrachloromethane; at 20℃; for 10h;	Methanol (14.5 mL, 360 mmol) and p-TsOH*H2O (0.68 g, 3.6 mmol) were added to a solution of (S)-valinic acid14a 5 (14.20 g, 120 mmol) in CCl4 (40 mL). The resulting mixture was refluxed for 10 h under anhydrous conditions. Next, the mixture was cooled to rt, washed with water (15 mL), saturated aqueous NaHCO3 (10 mL), dried over MgSO4 and concentrated under reduced pressure. The residue was distilled to give methyl ester 6 (13.03 g, 82%) as a colourless oil; bp 62-63 C/15 Torr; [alpha]D = +23.7 (c 1.00, CHCl3), lit.14b [alpha]D = +24.3 (c 1.00, CHCl3); 1H NMR (CDCl3) d 0.82 (d, J = 6.9 Hz, 3H, 3-Me), 0.98 (d, J = 6.9 Hz, 3H, 3-Me), 2.03 (sept. of d, J = 6.9, 3.6 Hz, 1H, 3-H), 2.83 (d, J = 6.2 Hz, 1H, OH), 3.75 (s, 3H, CO2Me), 4.01 (dd, J = 6.2, 3.6 Hz, 1H, 2-H); 13C NMR (CDCl3) d 15.9, 18.6, 32.1, 52.2, 75.0, 175.3; IR (film) numax: 3483, 1735 cm-1.
62.2%	With thionyl chloride; at 0 - 20℃; for 2h;	To a stirred solution of fV)-2-hydroxy-3 -methyl butanoic acid (1 g, 8.47 mmol) in anhydrous methanol (25 mL) at 0 C, was added thionyl chloride (1.236 mL, 16.93 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 2 h. The reaction mixture was concentrated to dryness under high vacuum. The residue was partitioned between sodium bicarbonate solution (25 ml) and DCM (50 mL). The organic layer was washed with ThO and saturated NaCl solution, dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to afford fV)-methyl 2-hydroxy-3- methylbutanoate (1.2 g, 5.27 mmol, 62.2%) as colourless oil. MR (300 MHz, methanol-) d ppm 3.96 (d, =4.9l Hz, 1H), 3.74 (s, 3H), 1.95 - 2.12 (m, 1H), 0.98 (d, =6.80 Hz, 3H), 0.92 (d, =6.80 Hz, 3H); LCMS(ES): m/z = 133.2[M+H]+.

Reference： [1]Patent: WO2020/47207,2020,A1 .Location in patent: Page/Page column 101
[2]Journal of the American Chemical Society,1990,vol. 112,p. 7659 - 7672
[3]Tetrahedron Letters,1989,vol. 30,p. 3757 - 3760
[4]Journal of Chemical Research, Miniprint,1998,p. 126 - 142
[5]Heterocycles,1999,vol. 51,p. 1321 - 1343
[6]Organic and Biomolecular Chemistry,2005,vol. 3,p. 3749 - 3756
[7]Tetrahedron Asymmetry,2011,vol. 22,p. 1448 - 1454
[8]Journal of Antibiotics,2002,vol. 55,p. 322 - 336
[9]Organic and Biomolecular Chemistry,2019,vol. 17,p. 3167 - 3180
[10]Patent: WO2019/136112,2019,A1 .Location in patent: Page/Page column 93; 94
[11]Journal of the Chemical Society. Perkin transactions I,1996,p. 1427 - 1433
[12]Journal of Organic Chemistry,1993,vol. 58,p. 1646 - 1648
[13]Chemische Berichte,1994,vol. 127,p. 1969 - 1980
[14]Heterocycles,2000,vol. 52,p. 151 - 158

5
[ 759-05-7 ]
[ 17407-55-5 ]

Reference： [1]Canadian Journal of Chemistry,1989,vol. 67,p. 1065 - 1070

6
[ 17407-55-5 ]
[ 28607-46-7 ]
(R)-2-((S)-2-Hydroxy-3-methyl-butyrylamino)-3-phenyl-propionic acid benzyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With 4-methyl-morpholine; 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran for 17h; Ambient temperature;

Reference： [1]Kagamizono; Nishino; Matsumoto; Kawashima; Kishimoto; Sakai; He; Chen; Adachi; Morimoto; Hanada [Journal of Antibiotics, 1995, vol. 48, # 12, p. 1407 - 1412]

7
[ 17407-55-5 ]
[ 74-88-4 ]
[ 24347-63-5 ]

Yield	Reaction Conditions	Operation in experiment
		A solution of sodium nitrite (4.30 g, 62.3 mmol) in water (17 mL) was added dropwise to a cooled (0 C) solution of (S)-valine (5.00 g, 42.7 mmol) in 1 N sulfuric acid (68 mL) and was allowed to stir for 1 h. The mixture was then warmed to rt and allowed to stir for 16 h. The solution was then extracted with Et2O (6 x 80 mL) and the organic layers were combined, dried over MgSO4, filtered and then concentrated in vacuo. Crude compound was carried on to subsequent transformation [5]. (2S)-2-Hydroxy-3-methylbutanoic acid was dissolved in acetone (100 mL). K2CO3 (7.60 g, 55 mmol) was then added and the solution was allowed to stir at rt for 1 h. MeI (4.00 mL, 64 mmol) was then added and the solution was heated to reflux for 20 h. The reaction was then allowed to cool to rt and then filtered and concentrated in vacuo. The crude material was distilled at 72 C at 23 torr to give a clear, colorless oil. Spectroscopic data is identical to that previously reported [6].

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 2292 - 2297
[2]Tetrahedron Letters,2017,vol. 58,p. 185 - 189

8
[ 205880-35-9 ]
[ 17407-55-5 ]
[ 54594-06-8 ]

Yield	Reaction Conditions	Operation in experiment
1: 63% 2: 71%	With hydrogenchloride at 90℃;

Reference： [1]Kardassis, Georgios; Brungs, Peter; Nothhelfer, Christoph; Steckhan, Eberhard [Tetrahedron, 1998, vol. 54, # 14, p. 3479 - 3488]

9
[ 17407-55-5 ]
[ 135112-28-6 ]
N²-tert-butoxycarbonyl-N³-benzyloxycarbonyl-D-2,3-diaminopropanoic acid [ No CAS ]
N-(9-fluorenylmethoxycarbonyl)-L-2-amino-5-(p-methoxyphenyl)pentanoic acid [ No CAS ]
(S)-2-{(S)-2-[(S)-2-((R)-2-Amino-3-benzyloxycarbonylamino-propionylamino)-pentanoyloxy]-3-methyl-butyrylamino}-5-(4-methoxy-phenyl)-pentanoic acid [ No CAS ]

Reference： [1]Bioscience, Biotechnology and Biochemistry,1998,vol. 62,p. 1799 - 1801

10
[ 17407-55-5 ]
[ 135112-27-5 ]
N²-tert-butoxycarbonyl-N³-benzyloxycarbonyl-D-2,3-diaminopropanoic acid [ No CAS ]
N-(9-fluorenylmethoxycarbonyl)-L-2-amino-5-(p-methoxyphenyl)pentanoic acid [ No CAS ]
(S)-2-{(S)-2-[(S)-2-((R)-2-Amino-3-benzyloxycarbonylamino-propionylamino)-butyryloxy]-3-methyl-butyrylamino}-5-(4-methoxy-phenyl)-pentanoic acid [ No CAS ]

Reference： [1]Bioscience, Biotechnology and Biochemistry,1998,vol. 62,p. 1799 - 1801

11
[ 17407-55-5 ]
[ 22171-15-9 ]
[ 431876-74-3 ]

Reference： [1]Organic Letters,2002,vol. 4,p. 1419 - 1422

12
[ 17407-55-5 ]
[ 13850-91-4 ]
(R)-2-(tert-Butoxycarbonyl-methyl-amino)-3-methyl-butyric acid (S)-1-carboxy-2-methyl-propyl ester [ No CAS ]

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

13
[ 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]

14
[ 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]

15
[ 17407-55-5 ]
[ 77-76-9 ]
[ 24347-63-5 ]

Yield	Reaction Conditions	Operation in experiment
27%	With methanol; chloro-trimethyl-silane;	The route to T116 begins with the Mitsunobu reaction of methyl ester (116-3) of (S)-(+)-2-hydroxy-3-methyl butyric acid (116-1, Spur, B. W. et. al. Tetrahedron Lett. 1998, 39, 8563-8566) and 5-fluoro-2-bromophenol (116-4). Subsequent Sonagashira coupling, hydrogenation and ester reduction provided Boc-T116a in 18% overall yield from 116-3.1H NMR (CDCl3, 300 MHz): delta 7.04 (m, 1H), 6.63 (dd, J=2.3, 11.4, 1H), 6.56 (dt, J=2.3, 8.2, 1H), 4.13 (m, 1H), 3.85 (d, J=4.7, 2H), 3.09 (m, 2H), 2.74 (m, 1H), 2.52 (m, 1H), 2.12 (m, 2H), 1.77 (m, 2H), 1.43 (s, 9H), 1.02 (d, J=7.0, 3H), 0.97 (d, J=6.7, 3H)MS: 256 (M+H-Boc)+
	toluene-4-sulfonic acid; In methanol; at 45℃; for 24h;	To a solution of L-amino acid 1 (25.0 mmol) in H2SO4 2N (37.5 ml, aqueous solution), cooled to 0 C., was added a solution of NaNO2 2N (2.57 g, 37.0 mmol) in water (9 ml). The temperature was maintained below 5 C. during the addition, and the mixture was stirred at such a temperature for 24 h. The solution was saturated with (NH4)2SO4, extracted with ether (3x25 ml), dried over Na2SO4 and evaporated under reduced pressure giving 2.72 g (23.0 mmol) of the corresponding ?-hydroxy acid as an oil. A solution of this oily material, p-toluenesulfonic acid monohydrate (0.03 g, 0.16 mmol) and dimethoxypropane (2.8 ml, 23.0 mmol) in methanol (1.15 ml) was heated at 45 C. for 24 h. The reaction mixture was evaporated under reduced pressure providing the corresponding {overscore (?)}hydroxy methyl ester 2 as an oil. This material was dissolved in anhydrous tetrahydrofuran (40 ml) and anhydrous N,N-dimethylformamide (12 ml), under an inert atmosphere, was cooled to 0 C. NaH (0.48 g, 20.0 mmol) was added and the mixture was stirred for 10 min. The corresponding bromide 3 (24.0 mmol) was added dropwise, and the mixture was allowed to reach room temperature. The reaction was monitored by TLC. When the reaction was complete, the reaction mixture was diluted in ether (130 ml) and washed with water (3x50 ml). The remaining organic layer was dried over Na2SO4 and evaporated under reduced pressure, providing the crude product 4, which was purified by flash column chromatography. (S)-Methyl 2-(2-fluorobenzyloxy)-3-methylbutanoate. This compound was prepared from L-valine and 2-fluorobenzyl bromide in 40 % yield: bp 70-72 C. (0.5 mm Hg); IR 1751, 1229 cm-1; 1H-NMR (? ppm, CDCl3) 7.49-6.97 (m, 4H), 4.71 (d, 1H, J=12.1 Hz), 4.49 (d, 1H, J=12.1 Hz), 3.74 (s, 3H), 3.71 (d, 1H, J=5.7 Hz), 2.18-2.00 (m, 1H), 0.96 (d, 3H, J=4.0 Hz), 0.92 (d, 3H, J=4.0 Hz); 13C-NMR (? ppm, CDCl3) 172.8, 163.1, 158.2, 130.3, 130.2, 129.5, 129.4, 124.0, 123.9, 115.3, 114.9, 83.6, 66.1, 66.0, 51.7, 31.6, 18.7, 17.7; [?]D25=-64.9 (c=1.27, CH2Cl2).
	With toluene-4-sulfonic acid; In methanol; at 45℃; for 18h;	EXAMPLE 17 Methyl(S)-2-hydroxy-3-methylbutyrate To a dry 15 mL flask was added (S)-(+)-2-hydroxy-3-methylbutyric acid (1.0 g, 8.47 mmol, 1 eq.), anhydrous methanol (1 mL), 2,2-dimethoxypropane (1.04 mL, 8.47 mmol, 1.0 eq.) and p-toluenesulfonic acid monohydrate (11 mg, 0.059 mmol, 0.007 eq.) under N2. The resulting solution was warmed to 45 C. and stirred for 18 hrs. The reaction was monitored by TLC. No starting material remained. All solvent was evaporated under reduced pressure. The residue was diluted with ethyl acetate (30 mL), and washed with saturated aqueous NaHCO3 (10 mL), water (3*10 mL) and brine (10 mL). The organic layers were dried over Na2SO4 and concentrated to afford crude compound 17 (670 mg), which was used directly in the next step without further purification. 1H NMR (300 MHz, CDCl3): consistent with proposed structure.

Reference： [1]Patent: US2008/194672,2008,A1 .Location in patent: Page/Page column 49-50
[2]Angewandte Chemie - International Edition,2005,vol. 44,p. 2903 - 2907
[3]Patent: US2006/211630,2006,A1 .Location in patent: Page/Page column 7
[4]Patent: US2009/163446,2009,A1 .Location in patent: Page/Page column 26

16
[ 17407-55-5 ]
[ 56414-96-1 ]
C₁₁H₂₀N₂O₄ [ No CAS ]

Reference： [1]Organic Letters,2007,vol. 9,p. 3615 - 3618

17
[ 17407-55-5 ]
[ 3519-30-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 84 percent / 18 h / 20 °C 2: toluene / 3 h / 95 °C 3: LiOH / H₂O; methanol; tetrahydrofuran / 3 h / 20 °C
	Multi-step reaction with 3 steps 1: 18 h / 20 °C 2: toluene / 3 h / 95 °C 3: aq. LiOH / tetrahydrofuran; methanol / 3 h / 20 °C
	Multi-step reaction with 3 steps 1: 4 h / 60 °C 2: DMAP; DCC / CH₂Cl₂ / 12 h / 20 °C 3: K₂CO₃ / methanol; H₂O / 12 h / 20 °C

Reference： [1]Tuccinardi, Tiziano; Martinelli, Adriano; Nuti, Elisa; Carelli, Paolo; Balzano, Federica; Uccello-Barretta, Gloria; Murphy, Gillian; Rossello, Armando [Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 12, p. 4260 - 4276]
[2]Rossello, Armando; Nuti, Elisa; Carelli, Paolo; Orlandini, Elisabetta; Macchia, Marco; Nencetti, Susanna; Zandomeneghi, Maurizio; Balzano, Federica; Barretta, Gloria Uccello; Albini, Adriana; Benelli, Roberto; Cercignani, Giovanni; Murphy, Gillian; Balsamo, Aldo [Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 5, p. 1321 - 1326]
[3]Yang; Li; Ng; Yan; Qu; Wu [Journal of Organic Chemistry, 2001, vol. 66, # 22, p. 7303 - 7312]

18
[ 20012-63-9 ]
[ 17407-55-5 ]
[ 1023754-87-1 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 5630 - 5631

19
[ 17407-55-5 ]
[ 960589-85-9 ]
[ 425386-60-3 ]

Yield	Reaction Conditions	Operation in experiment
41.43 kg	With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In ethanol; water at 0 - 40℃; for 4.5h; Large scale reaction; optical yield given as %ee;

Reference： [1]Location in patent: experimental part Pu, Yangwei John; Vaid, Radhe K.; Boini, Sathish K.; Towsley, Robert W.; Doecke, Christopher W.; Mitchell, David [Organic Process Research and Development, 2009, vol. 13, # 2, p. 310 - 314]

20
[ 17407-55-5 ]
[ CAS Unavailable ]
[ 425386-60-3 ]

Yield	Reaction Conditions	Operation in experiment
83%	Stage #1: (S)-2-Hydroxy-3-methylbutanoic acid; CH₄O₃S*C₁₄H₁₉N₃O₂ With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Stage #2: In water; acetone

Reference： [1]Location in patent: scheme or table Boini, Sathish K.; Vaid, Radhe K.; Moder, Kenneth P.; Mitchell, David [Synthesis, 2009, # 12, p. 1983 - 1986]

21
[ 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

22
[ 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

23
[ 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

24
[ 1344149-10-5 ]
[ 72-18-4 ]
[ 17407-55-5 ]
[ 73-32-5 ]
[ 2566-30-5 ]
[ 147-85-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; water; at 110℃; for 24h;	General Procedure: A sample of compounds 3-6 (0.1 mg each) was hydrolyzed with 6 N HCl (0.5 mL) at 110 &degC for 24 h. The hydrolysate was concentrated to dryness, resuspended in H2O (100 muL), and then analyzed by chiral HPLC. Amino acid units were analyzed by HPLC/MS chiral analysis [column: Chirobiotic TAG (250 x 4.6 mm), Supelco;solvent: MeOH/10 mM NH4OAc (40:60, pH 5.6); flow rate 0.5 mL/min; detection by ESIMS in positive ion mode (MRM scan)]. The retention times (tR min; MRM ion pair, parent -> product) of the authentic amino acids were as follows: L-Pro (12.3; 116 -> 70), D-Pro (32.0), L-Val (7.7; 118 -> 72), D-Val (17.0), L-Ile (8.2;132 -> 86.1), D-Ile (20.5), L-Phe (15.1; 166.2 -> 120.2), D-Phe(22.5), N-Me-L-Phe (21.2; 180 -> 134.2), N-Me-D-Phe (37.0). The hydrolysates showed peaks corresponding to L-amino acids at tR12.3, 7.7, 8.2, 15.1 and 21.2 min. The MS parameters used were as follows: DP 32, EP 4, CE 21.8, CXP 2.8, CUR 30, CAD medium, IS 4500, TEM 700, GS1 65, and GS2 65. The absolute configurations of the alpha-hydroxy acid units were analyzed by chiral HPLC analysis under different conditions; [column: CHIRALPAK MA (+) (50 x 4.6 mm); solvent: CH3CN/2 mM CuSO4 (10:90); flow rate1 mL/min; detection by UV (254 nm)]. The retention times (tRmin) of the authentic standards were as follows: (2S,3S)-Hmpa (30.5), (2R,3R)-Hmpa (17.0), (2S,3R)-Hmpa (24.1), (2R,3S)-Hmpa (14.0), (2S)-Hiva (8.9), (2R)-Hiva (5.0). The retention times of the samples corresponded to (2S,3S)-Hmpa (30.5) in compounds 3, 4,and 6, and (2S)-Hiva (8.9) in 5.

Reference： [1]Phytochemistry,2011,vol. 72,p. 2068 - 2074

25
maedamide [ No CAS ]
[ 17407-55-5 ]
[ 1509-35-9 ]
(2R,3S)-2-hydroxy-3-methylpentanoic acid [ No CAS ]
[ 56564-52-4 ]
[ 147-85-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride In water at 110℃; for 25h;	Determination of the absolute configuration in 1 except for an Ahppa moiety Maedamide (1) (0.9 mg) was treated with 9 N HCl (100 μL) for 25 h at 110 °C. The hydrolyzed product was evaporated to dryness and could be separated into each component. The retention times of the isolated components were matched with those of the corresponding authentic standards. [Conditions for HPLC separation: column, Cosmosil 5C18-PAQ (φ4.6 × 250 mm); flow rate, 1.0 mL/min; detection at 215 nm; solvent H2O. Retention times (min) of components: Pro (tR = 3.2 min), Ile (tR = 4.6 min), N-Me-Phe (tR = 12.8 min)], [Conditions for HPLC separation: column, ODS HG-5 (φ4.6 × 250 mm); flow rate, 1.0 mL/min; detection at 215 nm; solvent MeCN -H2O-TFA (10:90:0.1). Retention time (min) of component: valic acid (tR = 9.1 min)], [Conditions for HPLC separation: column, ODS HG-5 (φ4.6 × 250 mm); flow rate, 1.0 mL/min; detection at 215 nm; solvent MeCN-H2O-TFA (15:85:0.1). Retention time (min) of component: isoleucic acid (tR = 12.5 min)], Each fraction was dissolved in H2O (50 μL) and analyzed by chiral HPLC, and the retention times were compared to those of authentic standards. [DAICEL CHIRALPAK (MA+) ( φ4.6 × 50 mm); flow rate, 1.0 mL/min; detection at 254 nm; solvent 2.0 mM CuSO4, 2.0 mM CuSO4 - MeCN (90:10) and 2.0 mM CuSO4 - MeCN (90:15)] With 2.0 mM CuSO4, the retention times (tR min) for authentic standards were D-Pro (2.9), L-Pro (5.4), D-Ile (7.9), L-Ile (6.4), D-allo-Ile (15.2), Lallo-Ile (11.1). With 2.0 mM CuSO4 - MeCN (90:10), the retention times for authentic standards were D-valic acid (10.2), L-valic acid (15.9), N-Me-D-Phe (14.4) and N-Me-L-Phe (16.4). With 2.0 mM CuSO4 - MeCN (85:15), the retention times for authentic standards were D-isoleucic acid (16.1), L-isoleucic acid (26.8), D-allo-isoleucic acid (13.7) and L-alloisoleucic acid (22.4).The retention times (min) (and the respective HPLC conditions) of the amino acids in the hydrolysate were 5.4, 15.2 (100:0), 15.9, 14.4 (90:10), and 13.7 (85:15), indicating the presence of L-Pro, D-allo-Ile, L-valic acid, NMe-D-Phe and D-allo-isoleucic acid in the hydrolysate.

Reference： [1]Iwasaki, Arihiro; Ohno, Osamu; Sumimoto, Shinpei; Suda, Shoichiro; Suenaga, Kiyotake [Tetrahedron Letters, 2014, vol. 55, # 30, p. 4126 - 4128]

26
maedamide [ No CAS ]
[ 17407-55-5 ]
[ 1509-35-9 ]
[ 56564-52-4 ]
[ 147-85-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride In water at 110℃; for 25h;	3. Determination of the absolute configuration in 1 except for an Ahppa moiety. Maedamide (1) (0.9 mg) was treated with 9 N HCl (100 μL) for 25 h at 110 °C. The hydrolyzed product was evaporated to dryness and could be separated into each component. The retention times of the isolated components were matched with those of the corresponding authentic standards. [Conditions for HPLC separation: column, Cosmosil 5C18-PAQ (φ4.6 × 250 mm); flow rate, 1.0 mL/min; detection at 215 nm; solvent H2O. Retention times (min) of components: Pro (tR = 3.2 min), Ile (tR = 4.6 min), N-Me-Phe (tR = 12.8 min)], [Conditions for HPLC separation: column, ODS HG-5 (φ4.6 × 250 mm); flow rate, 1.0 mL/min; detection at 215 nm; solvent MeCN-H2O-TFA (10:90:0.1). Retention time (min) of component: valic acid (tR = 9.1 min)], [Conditions for HPLC separation: column, ODS HG-5 (φ4.6 × 250 mm); flow rate, 1.0 mL/min; detection at 215 nm; solvent MeCN-H2O-TFA (15:85:0.1). Retention time (min) of component: isoleucic acid (tR = 12.5 min)],

Reference： [1]Iwasaki, Arihiro; Ohno, Osamu; Sumimoto, Shinpei; Suda, Shoichiro; Suenaga, Kiyotake [Tetrahedron Letters, 2014, vol. 55, # 30, p. 4126 - 4128]

27
C₁₁H₁₇NO₄ [ No CAS ]
[ 3913-67-5 ]
[ 29475-64-7 ]
[ 17407-55-5 ]

Reference： [1]Organic Letters,2015,vol. 17,p. 5476 - 5479

28
Alloc-Me-Ala [ No CAS ]
N-Fmoc-N-methyl-L-threonine [ No CAS ]
2-chlorotrityl chloride polystyrene resin [ No CAS ]
[ 17407-55-5 ]
[ 68858-20-8 ]
[ 35661-39-3 ]
(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-methoxypropanoic acid [ No CAS ]
[ 103478-62-2 ]
[ 143674-78-6 ]
[ 138775-22-1 ]
C₆₂H₁₀₃N₁₀O₁₆Pol [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2015,vol. 2015,p. 7043 - 7052

29
Alloc-Me-Ala [ No CAS ]
N-Fmoc-N-methyl-L-threonine [ No CAS ]
[ 17407-55-5 ]
[ 68858-20-8 ]
[ 35661-39-3 ]
(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-methoxypropanoic acid [ No CAS ]
[ 103478-62-2 ]
[ 143674-78-6 ]
[ 138775-22-1 ]
C₇₈H₁₁₆N₁₀O₁₈ [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2015,vol. 2015,p. 7043 - 7052

30
[ 516-06-3 ]
[ 17407-55-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; sodium nitrite In water at 20℃; Cooling;	J To a solution of acid amino acid in iN H2SO4, a solution of NaNO2 in minimal quantity of water was added under cooling. The resulted mixture was stirred at room temperature for 1-3 days, saturated with Na2SO4, and extracted with a solvent likemethyl-tert-butyl ether or DCM. The organic layer was evaporated.

Reference： [1]Current Patent Assignee: NMD PHARMA DK - WO2016/202341, 2016, A1 Location in patent: Page/Page column 106

31
odobromoamide [ No CAS ]
[ 72-18-4 ]
[ 17407-55-5 ]
[ 2480-23-1 ]
[ 4125-98-8 ]
[ 147-85-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In water; at 105℃; for 12h;	Absolute Configurations of Amino Acid Residues in 1.Odobromoamide (1, 1.2 mg) was treated with 5 M HCl (0.5mL) at 105 C for 12 h. The hydrolysate was concentrated todryness and partitioned between H2O and EtOAc. The aqueouslayer was subjected to HPLC [Cosmosil HILIC (4.6 250mm), MeCN/10 mM AcONH4 = 85:15 at 1.0 mL/min, UV detection at 215 nm] to yield N-Me-Ile, N-Me-Val, Hmba, Val andPro. Each amino acid expect for Hmba was added with 0.1%solution of Nalpha-(5-fluoro-2,4-dinitrophenyl)-L-alaninamide (LFDAA, Marfey?s reagent, 200 L) in acetone and 0.5 MNaHCO3 (100 L) followed by heating at 40 C for 90 min.After cooling to room temperature, the reaction mixture wasneutralized with 2 M HCl (25 L) and diluted with MeOH(300 L). The solution was subjected to reversed-phase HPLC[Cosmosil 5C18-AR-II (4.6 250 mm), MeOH/20 mM AcONa = 60:40 (solvent A) or 50:50 (solvent B) at 1.0 mL/min,UV detection at 340 nm]. The L-FDAA derivatives of standardamino acids were prepared by the same procedure. The retention times (min) of the authentic standards were as follows: LN-Me-Ile (6.6), L-allo-N-Me-Ile (6.9), D-N-Me-Ile (11.6), Dallo-N-Me-Ile (12.2), L-N-Me-Val (5.3) and D-N-Me-Val (8.5)in solvent A, L-Val (6.8), D-Val (18.3), L-Pro (4.9) and D-Pro(6.5) in solvent B. The retention times and ESIMS product ions(m/z [M+Na]+) of the L-FDAA derivatives of N-Me-Ile and NMe-Val from the hydrolysate were 6.6 min (420.1) and 5.3 min(406.1) in solvent A, respectively, proving the configurationsof N-Me-Ile and N-Me-Val were L. The retention times andESIMS product ions (m/z [M+Na]+) of the L-FDAA derivatives of Val and Pro from the hydrolysate were 6.8 min (392.1)and 4.9 min (390.1) in solvent B, respectively, proving theconfigurations of Val and Pro were L

Reference： [1]Bulletin of the Chemical Society of Japan,2017,vol. 90,p. 436 - 440

32
[ 17407-55-5 ]
[ 57333-96-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 13 steps 1.1: sulfuric acid / 12 h / 100 - 110 °C / Dean-Stark 2.1: sodium hydride / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -20 - 20 °C 4.1: triethylamine / dichloromethane / 2.5 h / 0 - 20 °C 5.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 60 - 70 °C 6.1: hexaammonium heptamolybdate tetrahydrate / ethanol / 0.17 h / 0 °C 6.2: 12 h / 0 - 20 °C 7.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -70 - -60 °C 7.2: -70 - 20 °C 8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 55 - 60 °C 9.1: pyridinium chlorochromate / dichloromethane / 20 °C 10.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 24 h / 2280.15 - 2660.18 Torr 11.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 20 °C 12.1: n-butyllithium / tetrahydrofuran / 1 h / -70 - -60 °C 12.2: 1.5 h / -65 - -10 °C 13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Darkness
	Multi-step reaction with 13 steps 1.1: sulfuric acid / butan-1-ol / 12 h / 100 - 110 °C / Dean-Stark; Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 - 20 °C / Inert atmosphere 3.1: diisobutylaluminium hydride / toluene / 3 h / -20 - 20 °C / Inert atmosphere 4.1: triethylamine / dichloromethane / 2.5 h / 10 - 20 °C / Inert atmosphere 5.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 60 - 70 °C / Inert atmosphere 6.1: hexaammonium heptamolybdate tetrahydrate / ethanol / 0.17 h / 0 °C / Inert atmosphere 6.2: 12 h / 0 - 20 °C / Inert atmosphere 7.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -70 °C / Inert atmosphere 7.2: -70 - 20 °C / Inert atmosphere 8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 60 °C / Inert atmosphere 9.1: dipyridinium dichromate / dichloromethane / 20 °C 10.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 24 h / 2280.15 - 2660.18 Torr 11.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere 12.1: n-butyllithium / tetrahydrofuran / 1 h / -65 °C / Inert atmosphere 12.2: 1.5 h / -65 - -10 °C / Inert atmosphere 13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 40 h / 20 °C / Darkness

Reference： [1]Current Patent Assignee: YONSUNG FINE CHEMICAL CO LTD - KR2018/116959, 2018, A
[2]Lee, Seung Jong; Moon, Hyung Wook; Lee, Kee-Young; Oh, Chang Young; Kim, U Bin; Shin, Hyunik [Organic Process Research and Development, 2021, vol. 25, # 4, p. 982 - 987]

33
pithohirolide [ No CAS ]
[ 17407-55-5 ]
[ 20312-36-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; water at 110℃; for 12h;	Chiral HPLC analysis Compound 1 (0.5 mg) was hydrolyzed at 110 °C in 6M HCl (200 μl) for 12 h, and the reaction mixture was dried in a stream of N2. The residue was dissolved in 2 mM CuSO4 aqueous solution (200 μl) and subjected to HPLC analysis (Sumichiral OA-5000, 4.6 × 150 mm; 15% 2-propanol in2 mM CuSO4 aqueous solution; 1 ml min-1; UV 254 nm). Retention times for the standards were 6.2 min for (S)-αHpp, 10.1 min for (R)-αHpp, and 28.2 min for (S)-Hiv, and36.6 min for (R)-Hiv, while the hydrolysate of 1 gave peaks at 6.2 min and 28.2 min (Fig. S10).

Reference： [1]Zhang, Zhiwei; Zhou, Tao; Xing, Tian; Ishizaki, Takayuki; Okuda, Toru; Oku, Naoya; Igarashi, Yasuhiro [Journal of Antibiotics, 2021, vol. 74, # 7, p. 458 - 463]

34
cyclo(L-Val-D-O-Leu-D-Ala-L-O-Val)3 [ No CAS ]
[ 338-69-2 ]
[ 72-18-4 ]
[ 17407-55-5 ]
[ 20312-37-2 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: cyclo(L-Val-D-O-Leu-D-Ala-L-O-Val)3 With potassium hydroxide In methanol at 50℃; for 2h; Stage #2: With hydrogenchloride In methanol; water at 110℃; for 24h;	General procedure: To determine the stereochemistry of the single amino acids and a-hydroxy acids containedin the analyzed dipeptides forming the isocereulide structure, aliquots (~200 L) ofthe alkaline hydrolysates of 1 and 2, respectively, were further used for acidic hydrolysis(3 mL HCl, 6 M, 24 h, 110 C), adjusted to pH 7.0 with KOH (1 M), and freeze-dried [20].The lyophilisates were extracted with MeCN (5 mL), centrifuged (4200 rpm, 10 min), andseparated into the amino acid containing the salt residue and the a-hydroxy acid containingliquid phase. Remaining MeCN was evaporated under a stream of nitrogen. Inthe following, both aliquots of the acidic hydrolysate of 1 and 2 were put to enantioselectivederivatization. Therefore, the derivatization of the amino acids in cereulide (1) andisocereulide A (2), as well as the corresponding reference amino acids D/L-Ala and D/L-Val(50 mol each), was performed using OPA and IBLC [22] followed by SPE purificationconsidering Reference [20]. The methanolic eluate gained via SPE was analyzed via UPLCTOF-MS, applying the same mass spectrometric parameters as described for the alkalinehydrolysis. Chromatography was performed at 45 C and a flowrate of 0.4 mL/min on a2.1 150 mm, 1.7 m, BEH-C18 column (Waters, Manchester, UK) with aqueous HCOOH(0.1%) as Solvent A, and a mixture of MeCN/HCOOH (99.9/0.1; v/v) as Solvent B, whilestarting the gradient at 30% B for 3 min, increasing to 33% B in 3 min, to 50% B in 6 min,and to 100% B in 1 min, followed by holding 100% B for 1 min, decreasing to 30% B within0.5 min, and ending with an equilibration at 30% B for 1.5 min. The mass spectrometricdata, obtained during the analysis of the amino acid isoindole derivatives, was summarizedin the following: D-Ala derivative: accurate mass: m/z 377.1180, D (ppm): +2.4; calcd: m/z377.1171 (C18H21N2O5S); L-Ala derivative: accurate mass: m/z 377.1181, D (ppm): +2.7;calcd: m/z 377.1171 (C18H21N2O5S); D-Val derivative: accurate mass: m/z 405.1489, D (ppm):+1.2; calcd: m/z 405.1484 (C20H25N2O5S); L-Val derivative: accurate mass: m/z 405.1492,D (ppm): +2.0; calcd: m/z 405.1484 (C20H25N2O5S).

Reference： [1]Ehling-Schulz, Monika; Hofmann, Thomas F.; Kranzler, Markus; Stark, Timo D.; Walser, Veronika [Molecules, 2021, vol. 26, # 5]

35
C₅₈H₉₈N₆O₁₈ [ No CAS ]
[ 338-69-2 ]
[ 72-18-4 ]
[ 17407-55-5 ]
[ 20312-37-2 ]
(2S,3S)-2-Hydroxy-3-methylpentanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: C₅₈H₉₈N₆O₁₈ With potassium hydroxide In methanol at 50℃; for 2h; Stage #2: With hydrogenchloride In methanol; water at 110℃; for 24h;	General procedure: To determine the stereochemistry of the single amino acids and a-hydroxy acids containedin the analyzed dipeptides forming the isocereulide structure, aliquots (~200 L) ofthe alkaline hydrolysates of 1 and 2, respectively, were further used for acidic hydrolysis(3 mL HCl, 6 M, 24 h, 110 C), adjusted to pH 7.0 with KOH (1 M), and freeze-dried [20].The lyophilisates were extracted with MeCN (5 mL), centrifuged (4200 rpm, 10 min), andseparated into the amino acid containing the salt residue and the a-hydroxy acid containingliquid phase. Remaining MeCN was evaporated under a stream of nitrogen. Inthe following, both aliquots of the acidic hydrolysate of 1 and 2 were put to enantioselectivederivatization. Therefore, the derivatization of the amino acids in cereulide (1) andisocereulide A (2), as well as the corresponding reference amino acids D/L-Ala and D/L-Val(50 mol each), was performed using OPA and IBLC [22] followed by SPE purificationconsidering Reference [20]. The methanolic eluate gained via SPE was analyzed via UPLCTOF-MS, applying the same mass spectrometric parameters as described for the alkalinehydrolysis. Chromatography was performed at 45 C and a flowrate of 0.4 mL/min on a2.1 150 mm, 1.7 m, BEH-C18 column (Waters, Manchester, UK) with aqueous HCOOH(0.1%) as Solvent A, and a mixture of MeCN/HCOOH (99.9/0.1; v/v) as Solvent B, whilestarting the gradient at 30% B for 3 min, increasing to 33% B in 3 min, to 50% B in 6 min,and to 100% B in 1 min, followed by holding 100% B for 1 min, decreasing to 30% B within0.5 min, and ending with an equilibration at 30% B for 1.5 min. The mass spectrometricdata, obtained during the analysis of the amino acid isoindole derivatives, was summarizedin the following: D-Ala derivative: accurate mass: m/z 377.1180, D (ppm): +2.4; calcd: m/z377.1171 (C18H21N2O5S); L-Ala derivative: accurate mass: m/z 377.1181, D (ppm): +2.7;calcd: m/z 377.1171 (C18H21N2O5S); D-Val derivative: accurate mass: m/z 405.1489, D (ppm):+1.2; calcd: m/z 405.1484 (C20H25N2O5S); L-Val derivative: accurate mass: m/z 405.1492,D (ppm): +2.0; calcd: m/z 405.1484 (C20H25N2O5S).

Reference： [1]Ehling-Schulz, Monika; Hofmann, Thomas F.; Kranzler, Markus; Stark, Timo D.; Walser, Veronika [Molecules, 2021, vol. 26, # 5]

Same Skeleton Products

Related Products

Historical Records

Related Functional Groups of
[ 17407-55-5 ]

Aliphatic Chain Hydrocarbons

[ 21641-92-9 ]

(S)-2-Hydroxy-3,3-dimethylbutanoic acid

Similarity: 0.96

[ 13748-90-8 ]

(S)-2-Hydroxy-4-methylpentanoic acid

Similarity: 0.92

[ 20312-37-2 ]

(R)-2-Hydroxy-4-methylpentanoic acid

Similarity: 0.92

[ 3347-90-8 ]

(S)-2-Hydroxybutanoic acid

Similarity: 0.88

[ 1330-70-7 ]

Hydroxyoctadecanoic acid

Similarity: 0.84

Alcohols

[ 21641-92-9 ]

(S)-2-Hydroxy-3,3-dimethylbutanoic acid

Similarity: 0.96

[ 13748-90-8 ]

(S)-2-Hydroxy-4-methylpentanoic acid

Similarity: 0.92

[ 20312-37-2 ]

(R)-2-Hydroxy-4-methylpentanoic acid

Similarity: 0.92

[ 3347-90-8 ]

(S)-2-Hydroxybutanoic acid

Similarity: 0.88

[ 16841-19-3 ]

1-Hydroxycyclopentanecarboxylic acid

Similarity: 0.86

Carboxylic Acids

[ 21641-92-9 ]

(S)-2-Hydroxy-3,3-dimethylbutanoic acid

Similarity: 0.96

[ 13748-90-8 ]

(S)-2-Hydroxy-4-methylpentanoic acid

Similarity: 0.92

[ 20312-37-2 ]

(R)-2-Hydroxy-4-methylpentanoic acid

Similarity: 0.92

[ 3347-90-8 ]

(S)-2-Hydroxybutanoic acid

Similarity: 0.88

[ 16841-19-3 ]

1-Hydroxycyclopentanecarboxylic acid

Similarity: 0.86

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
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.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
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.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
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.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
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:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 17407-55-5 ] {[proInfo.proName]}

Quality Control of [ 17407-55-5 ]

Related Doc. of [ 17407-55-5 ]

Product Details of [ 17407-55-5 ]

Calculated chemistry of [ 17407-55-5 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 17407-55-5 ]

Application In Synthesis of [ 17407-55-5 ]

[ 17407-55-5 ] Synthesis Path-Upstream 1~8

[ 17407-55-5 ] Synthesis Path-Downstream 1~35

Related Functional Groups of [ 17407-55-5 ]

Aliphatic Chain Hydrocarbons

Alcohols

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 17407-55-5 ]