Acrylic acid (1S,2R)-1-benzyloxymethyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyl ester

Base Information

• Chemical Name: Acrylic acid (1S,2R)-1-benzyloxymethyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyl ester
• CAS No.: 632332-46-8
• Molecular Formula: C₃₂H₃₈O₄Si
• Molecular Weight: 514.737

Synonyms:Acrylic acid (1S,2R)-1-benzyloxymethyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyl ester

Chemical Property of Acrylic acid (1S,2R)-1-benzyloxymethyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyl ester

Chemical Property:

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Technology Process of Acrylic acid (1S,2R)-1-benzyloxymethyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyl ester

There total 2 articles about Acrylic acid (1S,2R)-1-benzyloxymethyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyl 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: 84.0%

acryloyl chloride (814-68-6,25189-84-8) + [(R)-2-((S)-1-Allyloxy-2-benzyloxy-ethyl)-but-3-enyloxy]-tert-butyl-diphenyl-silane (632332-43-5) → Acrylic acid (1S,2R)-1-benzyloxymethyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyl ester (632332-46-8)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -20 ℃; for 18h;

DOI:10.3987/COM-03-9815

Reference yield:

(2S,3R)-1-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-4-en-2-ol (365562-75-0) → Acrylic acid (1S,2R)-1-benzyloxymethyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyl ester (632332-46-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / Ag₂O / CH₂Cl₂ / 18 h / 20 °C

2: 84 percent / DMAP; (i-Pr)2NEt / CH₂Cl₂ / 18 h / -20 °C

With dmap; N-ethyl-N,N-diisopropylamine; silver(l) oxide; In dichloromethane;

DOI:10.3987/COM-03-9815

Reference yield: 100.0%

Acrylic acid (1S,2R)-1-benzyloxymethyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyl ester (632332-46-8) → (5R,6S)-6-Benzyloxymethyl-5-(tert-butyl-diphenyl-silanyloxymethyl)-5,6-dihydro-pyran-2-one

Guidance literature:

Grubbs catalyst first generation; In dichloromethane; Heating;

DOI:10.3987/COM-03-9815

upstream raw materials:

acryloyl chloride

[(R)-2-((S)-1-Allyloxy-2-benzyloxy-ethyl)-but-3-enyloxy]-tert-butyl-diphenyl-silane

(2S,3R)-1-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-4-en-2-ol

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