(S)-4-[(E)-(R)-2-(2-benzyloxyphenyl)-1-hydroxybut-2-enyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (S)-4-[(E)-(R)-2-(2-benzyloxyphenyl)-1-hydroxybut-2-enyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester
• CAS No.: 918305-02-9
• Molecular Formula: C₂₇H₃₅NO₅
• Molecular Weight: 453.579

Synonyms:(S)-4-[(E)-(R)-2-(2-benzyloxyphenyl)-1-hydroxybut-2-enyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property of (S)-4-[(E)-(R)-2-(2-benzyloxyphenyl)-1-hydroxybut-2-enyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property:

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Technology Process of (S)-4-[(E)-(R)-2-(2-benzyloxyphenyl)-1-hydroxybut-2-enyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

There total 1 articles about (S)-4-[(E)-(R)-2-(2-benzyloxyphenyl)-1-hydroxybut-2-enyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl 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: 51.0%

1-benzyloxy-2-[(1E)-1-iodoprop-1-en-1-yl]benzene (918304-79-7) + (4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (102308-32-7) → (S)-4-[(E)-(R)-2-(2-benzyloxyphenyl)-1-hydroxybut-2-enyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (918305-02-9) + (S)-4-[(E)-(S)-2-(2-benzyloxyphenyl)-1-hydroxybut-2-enyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (918304-80-0)

Guidance literature:

1-benzyloxy-2-[(1E)-1-iodoprop-1-en-1-yl]benzene; With tert.-butyl lithium; In diethyl ether; hexane; at -78 ℃; for 0.75h;

With magnesium bromide; In diethyl ether; hexane; benzene; at -78 ℃; for 0.5h;

(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester; In various solvents; at -78 - 20 ℃; for 17h; Further stages.;

DOI:10.1039/b609604b

Reference yield: 92.0%

(S)-4-[(E)-(R)-2-(2-benzyloxyphenyl)-1-hydroxybut-2-enyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (918305-02-9) + benzyl bromide (100-39-0) → C34H41NO5 (918305-11-0)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 65 ℃; for 6h;

DOI:10.1039/b609604b

Reference yield: 79.0%

(S)-4-[(E)-(R)-2-(2-benzyloxyphenyl)-1-hydroxybut-2-enyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (918305-02-9) + 2-Iodobenzyl bromide (40400-13-3) → (S)-4-[(E)-(R)-2-(2-benzyloxyphenyl)-1-(2-iodobenzyloxy)but-2-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (918305-03-0)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 55 ℃; for 20h;

DOI:10.1039/b609604b

upstream raw materials:

1-benzyloxy-2-[(1E)-1-iodoprop-1-en-1-yl]benzene

(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Downstream raw materials:

(S)-4-[(E)-(R)-2-(2-benzyloxyphenyl)-1-(2-iodobenzyloxy)but-2-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

C₃₄H₄₁NO₅

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