benzyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside

Base Information

• Chemical Name: benzyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside
• CAS No.: 91652-71-0
• Molecular Formula: C₃₂H₄₀O₆Si
• Molecular Weight: 548.751
• Mol file: 91652-71-0.mol

Synonyms:benzyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside

Chemical Property of benzyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside

There total 6 articles about benzyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside 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: 97.0%

benzyl 6-O-tetra-butyldiphenylsilyl-α-D-mannopyranoside (114894-82-5) + 2,2-dimethoxy-propane (77-76-9) → benzyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside (91652-71-0)

Guidance literature:

With camphor-10-sulfonic acid; In acetone; for 16h; Ambient temperature;

DOI:10.1016/S0040-4020(01)86850-2

Reference yield:

(2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol (15548-45-5) → benzyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside (91652-71-0)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / dimethylformamide / 20 °C

2: CSA / acetone

With 1H-imidazole; camphor-10-sulfonic acid; In N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.tetlet.2004.02.106

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → benzyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside (91652-71-0)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / dimethylformamide / 20 °C

2: CSA / acetone

With 1H-imidazole; camphor-10-sulfonic acid; In N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.tetlet.2004.02.106

upstream raw materials:

benzyl 6-O-tetra-butyldiphenylsilyl-α-D-mannopyranoside

2,2-dimethoxy-propane

acetone

(2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol

Downstream raw materials:

benzyl 4-O-acetyl-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside

benzyl 2,3-O-isopropylidene-4-O-acetyl-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside

benzyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->4)-6-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside

Methanesulfonic acid (3aS,4S,6R,7S,7aR)-4-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester