dibenzyl (2S)-2-[(3S)-3-benzyloxycarbonyl-3-(tert-butyldiphenylsilyloxy)propanoyloxy]butanedioate

Base Information

• Chemical Name: dibenzyl (2S)-2-[(3S)-3-benzyloxycarbonyl-3-(tert-butyldiphenylsilyloxy)propanoyloxy]butanedioate
• CAS No.: 276871-08-0
• Molecular Formula: C₄₅H₄₆O₉Si
• Molecular Weight: 758.94

Synonyms:dibenzyl (2S)-2-[(3S)-3-benzyloxycarbonyl-3-(tert-butyldiphenylsilyloxy)propanoyloxy]butanedioate

Chemical Property of dibenzyl (2S)-2-[(3S)-3-benzyloxycarbonyl-3-(tert-butyldiphenylsilyloxy)propanoyloxy]butanedioate

Chemical Property:

Purity/Quality:

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Technology Process of dibenzyl (2S)-2-[(3S)-3-benzyloxycarbonyl-3-(tert-butyldiphenylsilyloxy)propanoyloxy]butanedioate

There total 3 articles about dibenzyl (2S)-2-[(3S)-3-benzyloxycarbonyl-3-(tert-butyldiphenylsilyloxy)propanoyloxy]butanedioate 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%

dibenzyl (2S)-2-hydroxybutanedioate (85719-40-0) + (3S)-4-benzyloxy-3-(tert-butyldiphenylsilyloxy)-4-oxobutanoic acid (209415-18-9) → dibenzyl (2S)-2-[(3S)-3-benzyloxycarbonyl-3-(tert-butyldiphenylsilyloxy)propanoyloxy]butanedioate (276871-08-0)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 ℃; for 6h;

DOI:10.1002/1099-0690(200004)2000:7<1207::AID-EJOC1207>3.0.CO;2-2

Reference yield:

(S)-3-(Benzyloxycarbonyl)-3-hydroxypropanoic acid (66178-04-9) → dibenzyl (2S)-2-[(3S)-3-benzyloxycarbonyl-3-(tert-butyldiphenylsilyloxy)propanoyloxy]butanedioate (276871-08-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: DMAP / dimethylformamide / 28 h / 20 °C

1.2: 80 percent / TFA / tetrahydrofuran; H₂O / 2 h / 0 - 20 °C

2.1: 84 percent / DCC; DMAP / CH₂Cl₂ / 6 h / 0 °C

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide; 1.1: Esterification / 1.2: Hydrolysis / 2.1: Condensation;

DOI:10.1002/1099-0690(200004)2000:7<1207::AID-EJOC1207>3.0.CO;2-2

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → dibenzyl (2S)-2-[(3S)-3-benzyloxycarbonyl-3-(tert-butyldiphenylsilyloxy)propanoyloxy]butanedioate (276871-08-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: DMAP / dimethylformamide / 28 h / 20 °C

1.2: 80 percent / TFA / tetrahydrofuran; H₂O / 2 h / 0 - 20 °C

2.1: 84 percent / DCC; DMAP / CH₂Cl₂ / 6 h / 0 °C

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide; 1.1: Esterification / 1.2: Hydrolysis / 2.1: Condensation;

DOI:10.1002/1099-0690(200004)2000:7<1207::AID-EJOC1207>3.0.CO;2-2

upstream raw materials:

dibenzyl (2S)-2-hydroxybutanedioate

(3S)-4-benzyloxy-3-(tert-butyldiphenylsilyloxy)-4-oxobutanoic acid

(S)-3-(Benzyloxycarbonyl)-3-hydroxypropanoic acid

tert-butylchlorodiphenylsilane

Downstream raw materials:

dibenzyl (2S)-2-[(3S)-3-benzyloxycarbonyl-3-hydroxypropanoyloxy]butanedioate

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