methyl 5-O-(2,3-di-O-benzoyl-5-O-tert-butyldiphenylsilyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranoside

Base Information

• Chemical Name: methyl 5-O-(2,3-di-O-benzoyl-5-O-tert-butyldiphenylsilyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranoside
• CAS No.: 204918-62-7
• Molecular Formula: C₅₅H₅₄O₁₃Si
• Molecular Weight: 951.111
• Mol file: 204918-62-7.mol

Synonyms:methyl 5-O-(2,3-di-O-benzoyl-5-O-tert-butyldiphenylsilyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranoside

Chemical Property of methyl 5-O-(2,3-di-O-benzoyl-5-O-tert-butyldiphenylsilyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 5-O-(2,3-di-O-benzoyl-5-O-tert-butyldiphenylsilyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranoside

There total 13 articles about methyl 5-O-(2,3-di-O-benzoyl-5-O-tert-butyldiphenylsilyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranoside 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: 82.0%

methyl 2,3-di-O-benzoyl-α-D-arabinofuranoside (204918-51-4) + p-cresyl 2,3-di-O-benzoyl-5-O-tert-butyldiphenylsilyl-1-thio-α-D-arabinofuranoside (204918-56-9) → methyl 5-O-(2,3-di-O-benzoyl-5-O-tert-butyldiphenylsilyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranoside (204918-62-7)

Guidance literature:

With N-iodo-succinimide; silver trifluoromethanesulfonate; In dichloromethane; at -10 ℃;

DOI:10.1016/S0960-894X(98)00049-3

Reference yield:

1-(p-thiocresyl)-2,3,5-tri-O-acetyl-α-D-arabinofuranoside (204918-48-9) → methyl 5-O-(2,3-di-O-benzoyl-5-O-tert-butyldiphenylsilyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranoside (204918-62-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / CH₃ONa; methanol / 3 h / 20 °C

2: 83 percent / DMAP; pyridine / 3 h / 0 °C

3: 91 percent / pyridine / 3 h / 0 - 20 °C

4: 82 percent / N-iodosuccinimide; AgOSO₂CF₃ / CH₂Cl₂ / 0.08 h / 0 °C

With pyridine; methanol; dmap; N-iodo-succinimide; sodium methylate; silver trifluoromethanesulfonate; In dichloromethane; 1: deacetylation / 2: Substitution / 3: Substitution / 4: glycosylation;

DOI:10.1021/ja993543l

Reference yield:

(2R,3S,4S,5S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-tetrahydro-furan-3,4-diol → methyl 5-O-(2,3-di-O-benzoyl-5-O-tert-butyldiphenylsilyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranoside (204918-62-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 418 mg / pyridine / 0 - 20 °C

2: 89 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0 - 20 °C

3: 82 percent / N-iodosuccinimide; AgOSO₂CF₃ / CH₂Cl₂ / 0.08 h / 0 °C

With pyridine; N-iodo-succinimide; tetrabutyl ammonium fluoride; silver trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; 1: Substitution / 2: desilylation / 3: glycosylation;

DOI:10.1021/ja993543l

upstream raw materials:

methyl 2,3-di-O-benzoyl-α-D-arabinofuranoside

p-cresyl 2,3-di-O-benzoyl-5-O-tert-butyldiphenylsilyl-1-thio-α-D-arabinofuranoside

benzoyl chloride

1-(p-thiocresyl)-2,3,5-tri-O-acetyl-α-D-arabinofuranoside

Downstream raw materials:

methyl 5-O-[5-O-(2,3,5-tri-O-acetyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranosyl]-2,3-di-O-benzoyl-α-D-arabinofuranoside

methyl (2,3-di-O-benzoyl-α-D-arabinofuranosyl)-(1->5)-2,3-di-O-benzoyl-α-D-arabinofuranoside