S-phenyl 2,3-O-carbonyl-4-O-(tert-butyldimethylsilyl)-1-thio-α-L-rhamnopyranoside

Base Information

• Chemical Name: S-phenyl 2,3-O-carbonyl-4-O-(tert-butyldimethylsilyl)-1-thio-α-L-rhamnopyranoside
• CAS No.: 403646-44-6
• Molecular Formula: C₁₉H₂₈O₅SSi
• Molecular Weight: 396.58
• Mol file: 403646-44-6.mol

Synonyms:S-phenyl 2,3-O-carbonyl-4-O-(tert-butyldimethylsilyl)-1-thio-α-L-rhamnopyranoside

Chemical Property of S-phenyl 2,3-O-carbonyl-4-O-(tert-butyldimethylsilyl)-1-thio-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of S-phenyl 2,3-O-carbonyl-4-O-(tert-butyldimethylsilyl)-1-thio-α-L-rhamnopyranoside

There total 2 articles about S-phenyl 2,3-O-carbonyl-4-O-(tert-butyldimethylsilyl)-1-thio-α-L-rhamnopyranoside 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: 83.0%

tert-butyldimethylsilyl chloride (18162-48-6) + S-phenyl 2,3-O-carbonyl-1-thio-α-L-rhamnopyranoside (403646-43-5) → S-phenyl 2,3-O-carbonyl-4-O-(tert-butyldimethylsilyl)-1-thio-α-L-rhamnopyranoside (403646-44-6)

Guidance literature:

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

DOI:10.1021/jo0108818

Reference yield:

phenyl 1-thio-α-L-rhamnopyranose (1214-98-8,105026-40-2,127061-11-4,131724-82-8) → S-phenyl 2,3-O-carbonyl-4-O-(tert-butyldimethylsilyl)-1-thio-α-L-rhamnopyranoside (403646-44-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / pyridine; toluene / 1 h

2: 83 percent / imidazole / dimethylformamide

With 1H-imidazole; In pyridine; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo0108818

Reference yield: 63.0%

S-phenyl 2,3-O-carbonyl-4-O-(tert-butyldimethylsilyl)-1-thio-α-L-rhamnopyranoside (403646-44-6) + 4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-β-D-galactopyranoside (403646-55-9) → 4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-(2,3-O-carbonyl-4-O-(tert-butyldimethylsilyl)-α-L-rhamnopyranosyl)-β-D-galactopyranoside (403646-57-1)

Guidance literature:

With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; at -60 - 0 ℃;

DOI:10.1021/jo0108818

upstream raw materials:

tert-butyldimethylsilyl chloride

S-phenyl 2,3-O-carbonyl-1-thio-α-L-rhamnopyranoside

phenyl 1-thio-α-L-rhamnopyranose

Downstream raw materials:

4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-(2,3-O-carbonyl-4-O-(tert-butyldimethylsilyl)-α-L-rhamnopyranosyl)-β-D-galactopyranoside

4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-(2,3-O-carbonyl-α-L-rhamnopyranosyl)-β-D-galactopyranoside