4-allyl 1-benzyl (2S)-2-[(3S)-3-benzyloxycarbonyl-3-(tert-butyldiphenylsilyloxy)propanoyloxy]butanedioate

Base Information

Chemical Name:4-allyl 1-benzyl (2S)-2-[(3S)-3-benzyloxycarbonyl-3-(tert-butyldiphenylsilyloxy)propanoyloxy]butanedioate
CAS No.:276871-00-2
Molecular Formula:C₄₁H₄₄O₉Si
Molecular Weight:708.88
Hs Code.:

Synonyms:4-allyl 1-benzyl (2S)-2-[(3S)-3-benzyloxycarbonyl-3-(tert-butyldiphenylsilyloxy)propanoyloxy]butanedioate

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Chemical Property of 4-allyl 1-benzyl (2S)-2-[(3S)-3-benzyloxycarbonyl-3-(tert-butyldiphenylsilyloxy)propanoyloxy]butanedioate

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Technology Process of 4-allyl 1-benzyl (2S)-2-[(3S)-3-benzyloxycarbonyl-3-(tert-butyldiphenylsilyloxy)propanoyloxy]butanedioate

There total 4 articles about 4-allyl 1-benzyl (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:

: 276870-98-5
4-allyl 1-benzyl (2S)-2-hydroxybutanedioate

: 2-(tert-butyl-diphenyl-silanyloxy)-3-chlorocarbonyl-propionic acid benzyl ester

: 276871-00-2
4-allyl 1-benzyl (2S)-2-[(3S)-3-benzyloxycarbonyl-3-(tert-butyldiphenylsilyloxy)propanoyloxy]butanedioate

Guidance literature:: With pyridine; In dichloromethane; at -78 - 20 ℃;
DOI:10.1002/1099-0690(200004)2000:7<1207::AID-EJOC1207>3.0.CO;2-2

Reference yield:

: 66178-04-9
(S)-3-(Benzyloxycarbonyl)-3-hydroxypropanoic acid

: 276871-00-2
4-allyl 1-benzyl (2S)-2-[(3S)-3-benzyloxycarbonyl-3-(tert-butyldiphenylsilyloxy)propanoyloxy]butanedioate

Guidance literature:: Multi-step reaction with 2 steps

1: 92 percent / K₂CO₃; tetrabutyl ammonium bromide / dimethylformamide / 4 h / 20 °C

2: 5.96 g / pyridine / CH₂Cl₂ / -78 - 20 °C

With pyridine; tetrabutylammomium bromide; potassium carbonate; In dichloromethane; N,N-dimethyl-formamide; 1: Esterification / 2: Substitution;
DOI:10.1002/1099-0690(200004)2000:7<1207::AID-EJOC1207>3.0.CO;2-2

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 276871-00-2
4-allyl 1-benzyl (2S)-2-[(3S)-3-benzyloxycarbonyl-3-(tert-butyldiphenylsilyloxy)propanoyloxy]butanedioate

Guidance literature:: Multi-step reaction with 3 steps

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

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

2.1: oxalyl chloride; DMF / CH₂Cl₂ / 20 °C

3.1: 5.96 g / pyridine / CH₂Cl₂ / -78 - 20 °C

With pyridine; dmap; oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; N,N-dimethyl-formamide; 1.1: Esterification / 1.2: Hydrolysis / 2.1: Substitution / 3.1: Substitution;
DOI:10.1002/1099-0690(200004)2000:7<1207::AID-EJOC1207>3.0.CO;2-2