benzyl hydrogen (S)-2-(tert-butyldimethylsilyloxy)succinate

Base Information

• Chemical Name: benzyl hydrogen (S)-2-(tert-butyldimethylsilyloxy)succinate
• CAS No.: 309730-43-6
• Molecular Formula: C₁₇H₂₆O₅Si
• Molecular Weight: 338.476
• Mol file: 309730-43-6.mol

Synonyms:benzyl hydrogen (S)-2-(tert-butyldimethylsilyloxy)succinate

Chemical Property of benzyl hydrogen (S)-2-(tert-butyldimethylsilyloxy)succinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl hydrogen (S)-2-(tert-butyldimethylsilyloxy)succinate

There total 3 articles about benzyl hydrogen (S)-2-(tert-butyldimethylsilyloxy)succinate 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: 78.0%

(S)-3-(Benzyloxycarbonyl)-3-hydroxypropanoic acid (66178-04-9) + tert-butyldimethylsilyl chloride (18162-48-6) → benzyl hydrogen (S)-2-(tert-butyldimethylsilyloxy)succinate (309730-43-6)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 8h;

DOI:10.1021/jo0006573

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → benzyl hydrogen (S)-2-(tert-butyldimethylsilyloxy)succinate (309730-43-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: TFAA / 3 h / 0 °C

1.2: 88 percent / 4 h / 20 °C

2.1: 78 percent / imidazole / dimethylformamide / 8 h / 20 °C

With 1H-imidazole; trifluoroacetic anhydride; In N,N-dimethyl-formamide; 1.1: Substitution / 1.2: benzylation / 2.1: silylation;

DOI:10.1021/jo0006573

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → benzyl hydrogen (S)-2-(tert-butyldimethylsilyloxy)succinate (309730-43-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trifluoroacetic anhydride / 3 h / 0 °C

1.2: 20 °C

2.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C

With 1H-imidazole; trifluoroacetic anhydride; In N,N-dimethyl-formamide;

upstream raw materials:

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

tert-butyldimethylsilyl chloride

benzyl alcohol

Downstream raw materials:

Benzyl (S)-2-tert-butyldimethylsilyloxy-N-(2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranosyl)succinate

(S)-2-(tert-Butyl-dimethyl-silanyloxy)-N-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-succinamic acid benzyl ester

(S)-2-(tert-Butyl-dimethyl-silanyloxy)-N-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yl)-succinamic acid benzyl ester

benzyl tert-butyl (S)-2-(tert-butyldimethylsilyloxy)succinate