2'-(benzyloxycarbonyl)benzyl 4-O-benzyl-3-O-p-methoxybenzyl-2-O-pivaloyl-α-D-mannopyranoside

Base Information

• Chemical Name: 2'-(benzyloxycarbonyl)benzyl 4-O-benzyl-3-O-p-methoxybenzyl-2-O-pivaloyl-α-D-mannopyranoside
• CAS No.: 798557-33-2
• Molecular Formula: C₄₁H₄₆O₁₀
• Molecular Weight: 698.81
• Mol file: 798557-33-2.mol

Synonyms:2'-(benzyloxycarbonyl)benzyl 4-O-benzyl-3-O-p-methoxybenzyl-2-O-pivaloyl-α-D-mannopyranoside

Chemical Property of 2'-(benzyloxycarbonyl)benzyl 4-O-benzyl-3-O-p-methoxybenzyl-2-O-pivaloyl-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2'-(benzyloxycarbonyl)benzyl 4-O-benzyl-3-O-p-methoxybenzyl-2-O-pivaloyl-α-D-mannopyranoside

There total 5 articles about 2'-(benzyloxycarbonyl)benzyl 4-O-benzyl-3-O-p-methoxybenzyl-2-O-pivaloyl-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: 93.0%

2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-3-O-p-methoxybenzyl-2-O-pivaloyl-α-D-mannopyranoside (798557-32-1) → 2'-(benzyloxycarbonyl)benzyl 4-O-benzyl-3-O-p-methoxybenzyl-2-O-pivaloyl-α-D-mannopyranoside (798557-33-2)

Guidance literature:

2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-3-O-p-methoxybenzyl-2-O-pivaloyl-α-D-mannopyranoside; With di-n-butylboryl trifluoromethanesulfonate; borane; In tetrahydrofuran; at 0 ℃; for 3h;

With triethylamine; In tetrahydrofuran; for 1h;

DOI:10.1021/ol048648u

Reference yield:

pivaloyl chloride (3282-30-2) → 2'-(benzyloxycarbonyl)benzyl 4-O-benzyl-3-O-p-methoxybenzyl-2-O-pivaloyl-α-D-mannopyranoside (798557-33-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 89 percent / DMAP; Et₃N / CH₂Cl₂ / 3.5 h / 0 °C

2.1: BH₃; Bu₂BOTf / tetrahydrofuran / 3 h / 0 °C

2.2: 93 percent / Et₃N / tetrahydrofuran / 1 h

With dmap; di-n-butylboryl trifluoromethanesulfonate; borane; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol048648u

Reference yield:

p-methoxybenzyl chloride (824-94-2) → 2'-(benzyloxycarbonyl)benzyl 4-O-benzyl-3-O-p-methoxybenzyl-2-O-pivaloyl-α-D-mannopyranoside (798557-33-2)

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: 89 percent / DMAP; Et₃N / CH₂Cl₂ / 3.5 h / 0 °C

3.1: BH₃; Bu₂BOTf / tetrahydrofuran / 3 h / 0 °C

3.2: 93 percent / Et₃N / tetrahydrofuran / 1 h

With dmap; di-n-butylboryl trifluoromethanesulfonate; borane; di(n-butyl)tin oxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ol048648u

upstream raw materials:

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

pivaloyl chloride

p-methoxybenzyl chloride

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

Downstream raw materials:

2'-(benzyloxycarbonyl)benzyl 4-O-benzyl-6-deoxy-3-O-p-methoxybenzyl-2-O-pivaloyl-α-D-rhamnopyranoside

2'-(benzyloxycarbonyl)benzyl 4-O-benzyl-2-O-pivaloyl-α-D-rhamnopyranoside

2'-(benzyloxycarbonyl)benzyl 4-O-benzyl-6-deoxy-3-O-p-methoxybenzyl-6-iodo-2-O-pivaloyl-α-D-mannopyranoside