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

Base Information

Chemical Name:dibenzyl (2S)-2-[(3S)-3-benzyloxycarbonyl-3-hydroxypropanoyloxy]butanedioate
CAS No.:276871-09-1
Molecular Formula:C₂₉H₂₈O₉
Molecular Weight:520.536
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

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

There total 3 articles about dibenzyl (2S)-2-[(3S)-3-benzyloxycarbonyl-3-hydroxypropanoyloxy]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: 94.0%

: 276871-08-0
dibenzyl (2S)-2-[(3S)-3-benzyloxycarbonyl-3-(tert-butyldiphenylsilyloxy)propanoyloxy]butanedioate

: 276871-09-1
dibenzyl (2S)-2-[(3S)-3-benzyloxycarbonyl-3-hydroxypropanoyloxy]butanedioate

Guidance literature:: With 70percent HF; In pyridine; dichloromethane; at 20 ℃; for 15h;
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

: 276871-09-1
dibenzyl (2S)-2-[(3S)-3-benzyloxycarbonyl-3-hydroxypropanoyloxy]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: 84 percent / DCC; DMAP / CH₂Cl₂ / 6 h / 0 °C

3.1: 94 percent / 70percent HF / pyridine; CH₂Cl₂ / 15 h / 20 °C

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

Reference yield:

: 209415-18-9
(3S)-4-benzyloxy-3-(tert-butyldiphenylsilyloxy)-4-oxobutanoic acid

: 276871-09-1
dibenzyl (2S)-2-[(3S)-3-benzyloxycarbonyl-3-hydroxypropanoyloxy]butanedioate

Guidance literature:: Multi-step reaction with 2 steps

1: 84 percent / DCC; DMAP / CH₂Cl₂ / 6 h / 0 °C

2: 94 percent / 70percent HF / pyridine; CH₂Cl₂ / 15 h / 20 °C

With dmap; dicyclohexyl-carbodiimide; In pyridine; dichloromethane; 1: Condensation / 2: Hydrolysis;
DOI:10.1002/1099-0690(200004)2000:7<1207::AID-EJOC1207>3.0.CO;2-2