2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-2-O-tert-butyldimethylsilyl-α-D-mannopyranoside

Base Information

• Chemical Name: 2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-2-O-tert-butyldimethylsilyl-α-D-mannopyranoside
• CAS No.: 798557-23-0
• Molecular Formula: C₃₄H₄₂O₈Si
• Molecular Weight: 606.788
• Mol file: 798557-23-0.mol

Synonyms:2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-2-O-tert-butyldimethylsilyl-α-D-mannopyranoside

Chemical Property of 2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-2-O-tert-butyldimethylsilyl-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-2-O-tert-butyldimethylsilyl-α-D-mannopyranoside

There total 4 articles about 2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-2-O-tert-butyldimethylsilyl-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: 88.0%

2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-2-O-tert-butyldimethylsilyl-3-O-p-methoxybenzyl-α-D-mannopyranoside (798557-22-9) → 2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-2-O-tert-butyldimethylsilyl-α-D-mannopyranoside (798557-23-0)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 0 ℃; for 0.666667h;

DOI:10.1021/ol048648u

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-2-O-tert-butyldimethylsilyl-α-D-mannopyranoside (798557-23-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / imidazole / dimethylformamide / 5 h / 20 °C

2: 88 percent / DDQ / CH₂Cl₂; H₂O / 0.67 h / 0 °C

With 1H-imidazole; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ol048648u

Reference yield:

2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-α-D-mannopyranoside (365535-43-9) → 2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-2-O-tert-butyldimethylsilyl-α-D-mannopyranoside (798557-23-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Bu₂SnO / methanol / 1 h / 60 °C

1.2: 83 percent / Bu₄NI / dimethylformamide / 1.5 h / 90 °C

2.1: 83 percent / imidazole / dimethylformamide / 5 h / 20 °C

3.1: 88 percent / DDQ / CH₂Cl₂; H₂O / 0.67 h / 0 °C

With 1H-imidazole; di(n-butyl)tin oxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ol048648u

upstream raw materials:

2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-2-O-tert-butyldimethylsilyl-3-O-p-methoxybenzyl-α-D-mannopyranoside

tert-butyldimethylsilyl chloride

2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-α-D-mannopyranoside

2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-3-O-p-methoxybenzyl-α-D-mannopyranoside

Downstream raw materials:

2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-2-O-tert-butyldimethylsilyl-3-deoxy-3-methylene-α-D-arabino-hexopyranoside

2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-3-C-methyl-α-D-manno-hexopyranoside

2''-(benzyloxycarbonyl)benzyl 3,3'-anhydro-4,6-O-benzylidene-3-C-hydroxymethyl-α-D-manno-hexopyranoside

2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-3-deoxy-3-methylene-α-D-arabino-hexopyranoside