tert-butyl ((1S,2R)-1,3-dihydroxy-1-phenylpropan-2-yl)-carbamate

Base Information

• Chemical Name: tert-butyl ((1S,2R)-1,3-dihydroxy-1-phenylpropan-2-yl)-carbamate
• CAS No.: 1294479-62-1
• Molecular Formula: C₁₄H₂₁NO₄
• Molecular Weight: 267.325
• Mol file: 1294479-62-1.mol

Synonyms:tert-butyl ((1S,2R)-1,3-dihydroxy-1-phenylpropan-2-yl)-carbamate

Chemical Property of tert-butyl ((1S,2R)-1,3-dihydroxy-1-phenylpropan-2-yl)-carbamate

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl ((1S,2R)-1,3-dihydroxy-1-phenylpropan-2-yl)-carbamate

There total 10 articles about tert-butyl ((1S,2R)-1,3-dihydroxy-1-phenylpropan-2-yl)-carbamate 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:

(R)-4-[(S)-hydroxy(phenyl)methyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (1377320-83-6) → tert-butyl ((1S,2R)-1,3-dihydroxy-1-phenylpropan-2-yl)-carbamate (1294479-62-1)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 22 ℃; for 2.5h; Inert atmosphere;

DOI:10.1002/chem.201704277

Reference yield:

(4R)-(1-hydroxy-phenyl-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (488727-71-5,1377320-83-6) → tert-butyl ((1S,2R)-1,3-dihydroxy-1-phenylpropan-2-yl)-carbamate (1294479-62-1) + ((1R,2R)-2-hydroxy-1-hydroxymethyl-2-phenylethyl)carbamic acid tert-butyl ester (1009093-14-4)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 22 ℃; for 2.5h; Overall yield = 74 %; Overall yield = 510 mg; Inert atmosphere;

DOI:10.1021/acs.joc.8b00898

Reference yield:

ethyl (2R,3S)-3-hydroxy-2-(((4-nitrophenyl)sulfonyl)oxy)-3-phenylpropanoate (1116503-88-8) → tert-butyl ((1S,2R)-1,3-dihydroxy-1-phenylpropan-2-yl)-carbamate (1294479-62-1)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium azide / N,N-dimethyl-formamide

2: lithium borohydride / tetrahydrofuran

3: methanol

With lithium borohydride; sodium azide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2011.01.146

upstream raw materials:

ethyl (2R,3S)-3-hydroxy-2-(((4-nitrophenyl)sulfonyl)oxy)-3-phenylpropanoate

(2S,3S)-ethyl 2-azido-3-hydroxy-3-phenylpropanoate

di-tert-butyl dicarbonate

(1S,2R)-2-amino-1-phenylpropane-1,3-diol

Downstream raw materials:

(2S,3S)-2-amino-3-hydroxy-3-phenylpropanoic acid

(2S,3S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-hydroxy-3-phenylpropanoic acid