(2S,3S)-2-tert-butoxycarbonylamino-5-methanesulfonyloxy-3-phenyl-pentanoic acid methyl ester

Base Information

Chemical Name:(2S,3S)-2-tert-butoxycarbonylamino-5-methanesulfonyloxy-3-phenyl-pentanoic acid methyl ester
CAS No.:515173-95-2
Molecular Formula:C₁₈H₂₇NO₇S
Molecular Weight:401.481
Hs Code.:

Synonyms:(2S,3S)-2-tert-butoxycarbonylamino-5-methanesulfonyloxy-3-phenyl-pentanoic acid methyl ester

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Chemical Property of (2S,3S)-2-tert-butoxycarbonylamino-5-methanesulfonyloxy-3-phenyl-pentanoic acid methyl ester

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Technology Process of (2S,3S)-2-tert-butoxycarbonylamino-5-methanesulfonyloxy-3-phenyl-pentanoic acid methyl ester

There total 5 articles about (2S,3S)-2-tert-butoxycarbonylamino-5-methanesulfonyloxy-3-phenyl-pentanoic 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: 76.0%

: 186581-53-3,908094-01-9,334-88-3
diazomethane

: 515173-92-9
(1'S,4S)-4-(3'-methanesulfonyloxy-1'-phenylpropyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 515173-95-2
(2S,3S)-2-tert-butoxycarbonylamino-5-methanesulfonyloxy-3-phenyl-pentanoic acid methyl ester

Guidance literature:: (1'S,4S)-4-(3'-methanesulfonyloxy-1'-phenylpropyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester; With chromium(VI) oxide; sulfuric acid; In acetone; at 0 ℃; for 4h;

diazomethane; In diethyl ether;
DOI:10.1016/S0040-4020(02)01405-9

Reference yield:

: 95715-87-0
(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

: 515173-95-2
(2S,3S)-2-tert-butoxycarbonylamino-5-methanesulfonyloxy-3-phenyl-pentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 85 percent / benzene / 36 h / 20 °C

2.1: 64 percent / CuCN; Me₃SiCl / tetrahydrofuran; diethyl ether / -78 - 0 °C

3.1: 97 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 20 °C

4.1: 96 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

5.1: CrO₃; H₂SO₄ / acetone / 4 h / 0 °C

5.2: 76 percent / diethyl ether

With chromium(VI) oxide; lithium aluminium tetrahydride; chloro-trimethyl-silane; sulfuric acid; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; acetone; benzene; 5.1: Jones oxidation;
DOI:10.1016/S0040-4020(02)01405-9

Reference yield:

: 134525-18-1,131713-27-4,144070-31-5,149406-02-0
(2E',4S)-4-(2'-ethoxycarbonyl-vinyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 515173-95-2
(2S,3S)-2-tert-butoxycarbonylamino-5-methanesulfonyloxy-3-phenyl-pentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 64 percent / CuCN; Me₃SiCl / tetrahydrofuran; diethyl ether / -78 - 0 °C

2.1: 97 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 20 °C

3.1: 96 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

4.1: CrO₃; H₂SO₄ / acetone / 4 h / 0 °C

4.2: 76 percent / diethyl ether

With chromium(VI) oxide; lithium aluminium tetrahydride; chloro-trimethyl-silane; sulfuric acid; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; acetone; 4.1: Jones oxidation;
DOI:10.1016/S0040-4020(02)01405-9