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CAS No.: | 165727-45-7 |
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Name: | (1S, 2S)-(1-BENZYL-3-CHLORO-2-HYDROXY-PROPYL)-CARBAMIC ACID TERT-BUTYL ESTER |
Article Data: | 30 |
Molecular Structure: | |
Formula: | C15H22ClNO3 |
Molecular Weight: | 299.798 |
Synonyms: | Carbamicacid, [(1S,2S)-3-chloro-2-hydroxy-1-(phenylmethyl)propyl]-, 1,1-dimethylethylester (9CI);Carbamic acid, [3-chloro-2-hydroxy-1-(phenylmethyl)propyl]-,1,1-dimethylethyl ester, [S-(R*,R*)]-;(2S,3S)-(-)-3-tert-Butoxycarbonylamino-1-chloro-2-hydroxy-4-phenylbutane;(2S,3S)-3-(tert-Butoxycarbonylamino)-1-chloro-2-hydroxy-4-phenylbutane;(2S,3S)-N-tert-Butoxycarbonyl-3-amino-1-chloro-2-hydroxy-4-phenylbutane;[(1S)-1-((1S)-2-Chloro-1-hydroxyethyl)-2-phenylethyl]carbamic acid tert-butylester; |
EINECS: | 1312995-182-4 |
Density: | 1.153 g/cm3 |
Boiling Point: | 460.5 °C at 760 mmHg |
Flash Point: | 232.3 °C |
Appearance: | White to off-white powder |
PSA: | 58.56000 |
LogP: | 3.11300 |
(S)-tert-butyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate
tert-butyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate
Conditions | Yield |
---|---|
With isopropyl alcohol; aluminum tri-tert-butoxide In dichloromethane at 50℃; Product distribution / selectivity; Meerwein-Ponndorf-Verley Reduction; Inert atmosphere; | 95% |
With aluminum sec-butoxide In 2-methyl-propan-1-ol; toluene at 15 - 20℃; Large scale; | 95% |
With C38H40ClN2O3RhS In dichloromethane at 25℃; for 1h; Catalytic behavior; Schlenk technique; diastereoselective reaction; | 93% |
(S)-tert-butyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate
isopropyl alcohol
tert-butyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate
Conditions | Yield |
---|---|
With diisobutylaluminium hydride In toluene | 90% |
(S)-tert-butyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate
A
tert-butyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate
B
(2R,3S)-1-Chloro-2-hydroxy-3-N-(tert-butoxycarbonyl)amino-4-phenylbutane
D
(1R,2S)[3-chloro-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
With potassium phosphate buffer; Streptomyces nodosus SC 13149 at 28℃; for 48h; pH=6.8; microbial reduction; | A 62% B n/a C n/a D n/a |
(S)-tert-butyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate
A
tert-butyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate
B
(2R,3S)-1-Chloro-2-hydroxy-3-N-(tert-butoxycarbonyl)amino-4-phenylbutane
Conditions | Yield |
---|---|
With sodium tetrahydroborate In tetrahydrofuran; water at 0℃; for 0.75h; | A 50% B n/a |
With sodium tetrahydroborate In tetrahydrofuran; water at 0℃; for 0.75h; | A n/a B 50% |
With sodium tetrahydroborate In ethanol; toluene at -78 - 0℃; for 8h; | A 7.8 g B n/a |
(S)-tert-butyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate
tert-butyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate
Conditions | Yield |
---|---|
With sodium borohydrid In tetrahydrofuran; water; ethyl acetate | 50% |
di-tert-butyl dicarbonate
tert-butyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate
Conditions | Yield |
---|---|
With triethylamine | |
With triethylamine In tetrahydrofuran at 20℃; Cooling with ice; |
(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester
tert-butyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: LDA / tetrahydrofuran / 0.5 h / -78 °C 2: 7.8 g / NaBH4 / toluene; ethanol / 8 h / -78 - 0 °C View Scheme |
N-t-butoxycarbonyl-L-phenylalanine 4-nitrophenyl ester
tert-butyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: t-BuOK / tetrahydrofuran / 2 h / Heating 1.2: tetrahydrofuran / 4 h / 0 °C 2.1: 81 percent / LiCl; MeSO3H / tetrahydrofuran / 2 h / 70 °C 3.1: 50 percent / NaBH4 / tetrahydrofuran; H2O / 0.75 h / 0 °C View Scheme |
tert-butyl (S)-(4-(dimethyl(oxo)-λ6-sulfanylidene)-3-oxo-1-phenylbutan-2-yl)carbamate
tert-butyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 81 percent / LiCl; MeSO3H / tetrahydrofuran / 2 h / 70 °C 2: 50 percent / NaBH4 / tetrahydrofuran; H2O / 0.75 h / 0 °C View Scheme |
(2S)-N,N-dibenzylphenylalaninal
tert-butyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: Li / tetrahydrofuran / -55 °C 2: 97 percent / H2 / Pd(OH)2/C / 760 Torr 3: Et3N View Scheme | |
Multi-step reaction with 3 steps 1: lithium / tetrahydrofuran / 3 h / -65 °C / Inert atmosphere 2: palladium hydroxide on carbon; hydrogen / methanol / 4 h / 20 °C / 760.05 Torr 3: triethylamine / tetrahydrofuran / 20 °C / Cooling with ice View Scheme |
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The (1S,2S)-(1-Benzyl-3-chloro-2-hydroxypropyl)carbamic acid tert-butyl ester is a kind of organic compounds with cas registry number of 165727-45-7. It has a systematic name which is called tert-butyl [(1S,2S)-1-benzyl-3-chloro-2-hydroxypropyl]carbamate.
The physical properties about this chemical are: (1)ACD/LogP: 3.38; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.38; (4)ACD/LogD (pH 7.4): 3.38; (5)ACD/BCF (pH 5.5): 218.91; (6)ACD/BCF (pH 7.4): 218.9; (7)ACD/KOC (pH 5.5): 1647.29; (8)ACD/KOC (pH 7.4): 1647.22; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 8; (12)Index of Refraction: 1.527; (13)Molar Refractivity: 79.86 cm3; (14)Molar Volume: 259.7 cm3; (15)Surface Tension: 41.6 dyne/cm; (16)Density: 1.153 g/cm3; (17)Flash Point: 232.3 °C; (18)Enthalpy of Vaporization: 75.98 kJ/mol; (19)Boiling Point: 460.5 °C at 760 mmHg; (20)Vapour Pressure: 2.83E-09 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES: ClC[C@@H](O)[C@@H](NC(=O)OC(C)(C)C)Cc1ccccc1;
(2)InChI: InChI=1/C15H22ClNO3/c1-15(2,3)20-14(19)17-12(13(18)10-16)9-11-7-5-4-6-8-11/h4-8,12-13,18H,9-10H2,1-3H3,(H,17,19)/t12-,13+/m0/s1;
(3)InChIKey: GFGQSTIUFXHAJS-QWHCGFSZBV