(1R,2S)[3-chloro-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid 1,1-dimethylethyl ester

Base Information

• Chemical Name: (1R,2S)[3-chloro-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid 1,1-dimethylethyl ester
• CAS No.: 923601-69-8
• Molecular Formula: C₁₅H₂₂ClNO₃
• Molecular Weight: 299.798

Synonyms:(1R,2S)[3-chloro-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid 1,1-dimethylethyl ester

Chemical Property of (1R,2S)[3-chloro-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid 1,1-dimethylethyl ester

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Technology Process of (1R,2S)[3-chloro-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid 1,1-dimethylethyl ester

There total 7 articles about (1R,2S)[3-chloro-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid 1,1-dimethylethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

(R)-(1-benzyl-3-chloro-2-oxopropyl)carbamic acid t-butyl ester (150935-37-8) → (1R,2S)[3-chloro-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid 1,1-dimethylethyl ester (923601-69-8)

Guidance literature:

With aluminum isopropoxide; isopropyl alcohol; for 3h; optical yield given as %de; diastereoselective reaction; Reflux;

Reference yield: 62.0%

(S)-tert-butyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate (102123-74-0) → tert-butyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate (165727-45-7) + (2R,3S)-1-Chloro-2-hydroxy-3-N-(tert-butoxycarbonyl)amino-4-phenylbutane (162536-40-5) + (1R,2R)[3-chloro-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid 1,1-dimethylethyl ester + (1R,2S)[3-chloro-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid 1,1-dimethylethyl ester (923601-69-8)

Guidance literature:

With potassium phosphate buffer; Streptomyces nodosus SC 13149; at 28 ℃; for 48h; pH=6.8;

DOI:10.1007/s11746-999-0139-7

Reference yield:

(R)-(1-benzyl-3-chloro-2-oxopropyl)carbamic acid t-butyl ester (150935-37-8) → (1R,2R)[3-chloro-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid 1,1-dimethylethyl ester + (1R,2S)[3-chloro-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid 1,1-dimethylethyl ester (923601-69-8)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; water; at 0 ℃; for 0.5h;

upstream raw materials:

(S)-tert-butyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate

(R)-(1-benzyl-3-chloro-2-oxopropyl)carbamic acid t-butyl ester

D-(R)-phenylalanine

D-phenylalanine methyl ester

Downstream raw materials:

tert-butyl [(2R,3R)]-(-)-(1-oxiranyl-2-phenylethyl)carbamate

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (2R,3S)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl carbamate

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