(2S,3R)-3-(3-acetoxy-4-benzyloxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid methyl ester

Base Information

• Chemical Name: (2S,3R)-3-(3-acetoxy-4-benzyloxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid methyl ester
• CAS No.: 870137-21-6
• Molecular Formula: C₂₅H₃₁NO₈
• Molecular Weight: 473.523

Synonyms:(2S,3R)-3-(3-acetoxy-4-benzyloxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid methyl ester

Chemical Property of (2S,3R)-3-(3-acetoxy-4-benzyloxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (2S,3R)-3-(3-acetoxy-4-benzyloxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid methyl ester

There total 3 articles about (2S,3R)-3-(3-acetoxy-4-benzyloxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid methyl 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: 84.0%

(4S,5R)-5-(3-acetoxy-4-benzyloxyphenyl)-2-(4-methoxyphenyl)-3-methyloxazolidine-4-carboxylic acid methyl ester (821006-10-4) + di-tert-butyl dicarbonate (24424-99-5) → (2S,3R)-3-(3-acetoxy-4-benzyloxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid methyl ester (870137-21-6)

Guidance literature:

(4S,5R)-5-(3-acetoxy-4-benzyloxyphenyl)-2-(4-methoxyphenyl)-3-methyloxazolidine-4-carboxylic acid methyl ester; With hydrogenchloride; In 1,4-dioxane; at 1 ℃; for 20h;

di-tert-butyl dicarbonate; With sodium hydrogencarbonate; In 1,4-dioxane; at 20 ℃; for 20h; Further stages.;

DOI:10.1021/ja710363p

Reference yield:

(4S,5R)-5-(3-acetoxy-4-benzyloxyphenyl)-2-(4-methoxyphenyl)-3-methyloxazolidine-4-carboxylic acid methyl ester (821006-10-4) → (2S,3R)-3-(3-acetoxy-4-benzyloxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid methyl ester (870137-21-6)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. HCl

With hydrogenchloride;

DOI:10.1021/ol052287g

Reference yield:

(4S,5R)-3-(3-acetoxy-4-benzyloxyphenyl)-3-hydroxy-2-methylaminopropionic acid methyl ester (821006-11-5) + di-tert-butyl dicarbonate (24424-99-5) → (2S,3R)-3-(3-acetoxy-4-benzyloxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid methyl ester (870137-21-6)

Guidance literature:

DOI:10.1021/ol052287g

upstream raw materials:

(4S,5R)-3-(3-acetoxy-4-benzyloxyphenyl)-3-hydroxy-2-methylaminopropionic acid methyl ester

di-tert-butyl dicarbonate

(4S,5R)-5-(3-acetoxy-4-benzyloxyphenyl)-2-(4-methoxyphenyl)-3-methyloxazolidine-4-carboxylic acid methyl ester

Downstream raw materials:

(2S,3R)-3-(4-benzyloxy-3-{(R)-1-[(S)-((R)-2-benzyloxycarbonylamino-3-methylbutyrylamino)-(tert-butoxycarbonylmethylcarbamoy)methyl]-1-methylprop-2-ynyloxy}phenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester

(2S,3R)-3-(4-benzyloxy-3-{(R)-1-[(S)-(tert-butoxycarbonylmethylcarbamoyl)-(2-nitrobenzenesulfonylamino)methyl]-1-methylprop-2-ynyloxy}phenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester

(2S,3R)-3-(3-{(R)-1-[(S)-amino-(tert-butoxycarbonylmethylcarbamoyl)methyl]-1-methylprop-2-ynyloxy}-4-benzyloxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester

(2S,3R)-3-(4-benzyloxy-3-hydroxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester

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