(+)-(2S,3R)-methyl 3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropanoate

Base Information

• Chemical Name: (+)-(2S,3R)-methyl 3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropanoate
• CAS No.: 161759-90-6
• Molecular Formula: C₁₅H₂₁NO₅
• Molecular Weight: 295.335

Synonyms:(+)-(2S,3R)-methyl 3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropanoate

Chemical Property of (+)-(2S,3R)-methyl 3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropanoate

Chemical Property:

• Melting Point: 131-132 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• Boiling Point: 443.3±45.0 °C(Predicted)
• Density: 1.170±0.06 g/cm3(Predicted)

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

(2S,3R)-N-Boc-3-phenylIsoserineMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (+)-(2S,3R)-methyl 3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropanoate

There total 36 articles about (+)-(2S,3R)-methyl 3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropanoate 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: 93.6%

di-tert-butyl dicarbonate (24424-99-5) + Methyl (2S,3R)-(-)-2-hydroxy-3-azido-3-phenyl-propionate (129866-72-4) → (+)-(2S,3R)-methyl 3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropanoate (161759-90-6)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethyl acetate; at 20 ℃; for 2h; under 1125.11 Torr;

DOI:10.3987/COM-10-11931

Reference yield: 93.0%

(4R,5S)-2,2-Dimethyl-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-methyl ester (215171-14-5) → (+)-(2S,3R)-methyl 3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropanoate (161759-90-6)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; for 2h; Heating;

DOI:10.1016/S0040-4020(98)00741-8

Reference yield: 91.0%

di-tert-butyl dicarbonate (24424-99-5) + (+)-(2S,3R)-methyl 3-amino-2-hydroxy-3-phenylpropanoate (322407-45-4) → (+)-(2S,3R)-methyl 3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropanoate (161759-90-6)

Guidance literature:

DOI:10.1002/jhet.5570420430

upstream raw materials:

methyl (2S,3R)-3-(N-tert-butoxycarbonylamino)-2-benzoyloxy-3-phenylpropionate

N-chloro-N-sodio-tert-butylcarbamate

Methyl cinnamate

(4R,5S)-2,2-Dimethyl-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-methyl ester

Downstream raw materials:

(2*,4R,5S)-methyl N-tert-butoxycarbonyl-2-(4'-methoxy)phenyl-4-phenyl-1,3-oxazolidine-5-methionate

(2S,3R)-3-((tert-butoxycarbonyl)amino)-3-phenyl-1,2-propanediol

2'-epi 3'-epi N-debenzoyl-N-tert-butoxycarbonyl-10-deacetyl taxol

(2*,4R,5S)-N-tert-butoxycarbonyl-2-(4'-methoxy)phenyl-4-phenyl-1,3-oxazolidine-5-formic acid

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