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

Base Information

• Chemical Name: 2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-2-O-tert-butyldimethylsilyl-3-deoxy-3-methylene-α-D-arabino-hexopyranoside
• CAS No.: 798557-25-2
• Molecular Formula: C₃₅H₄₂O₇Si
• Molecular Weight: 602.8
• Mol file: 798557-25-2.mol

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

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

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-3-deoxy-3-methylene-α-D-arabino-hexopyranoside

There total 6 articles about 2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-2-O-tert-butyldimethylsilyl-3-deoxy-3-methylene-α-D-arabino-hexopyranoside 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: 92.0%

Methyltriphenylphosphonium bromide (1779-49-3) + 2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-2-O-tert-butyldimethylsilyl-α-D-arabino-hexopyranosid-3-uloside (798557-24-1) → 2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-2-O-tert-butyldimethylsilyl-3-deoxy-3-methylene-α-D-arabino-hexopyranoside (798557-25-2)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at 0 ℃; for 5.5h;

DOI:10.1021/ol048648u

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-2-O-tert-butyldimethylsilyl-3-deoxy-3-methylene-α-D-arabino-hexopyranoside (798557-25-2)

Guidance literature:

Multi-step reaction with 4 steps

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

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

3: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 4 h / 20 °C

4: 92 percent / n-BuLi / tetrahydrofuran / 5.5 h / 0 °C

With 1H-imidazole; n-butyllithium; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 3: Dess-Martin oxidation;

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-3-deoxy-3-methylene-α-D-arabino-hexopyranoside (798557-25-2)

Guidance literature:

Multi-step reaction with 5 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

4.1: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 4 h / 20 °C

5.1: 92 percent / n-BuLi / tetrahydrofuran / 5.5 h / 0 °C

With 1H-imidazole; n-butyllithium; di(n-butyl)tin oxide; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 4.1: Dess-Martin oxidation;

DOI:10.1021/ol048648u

upstream raw materials:

Methyltriphenylphosphonium bromide

2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-2-O-tert-butyldimethylsilyl-α-D-arabino-hexopyranosid-3-uloside

tert-butyldimethylsilyl chloride

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

Downstream raw materials:

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