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

Base Information

• Chemical Name: 2''-(benzyloxycarbonyl)benzyl 3,3'-anhydro-4,6-O-benzylidene-3-C-hydroxymethyl-α-D-manno-hexopyranoside
• CAS No.: 798557-27-4
• Molecular Formula: C₂₉H₂₈O₈
• Molecular Weight: 504.537
• Mol file: 798557-27-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about 2''-(benzyloxycarbonyl)benzyl 3,3'-anhydro-4,6-O-benzylidene-3-C-hydroxymethyl-α-D-manno-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: 80.0%

2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-3-deoxy-3-methylene-α-D-arabino-hexopyranoside (798557-26-3) → 2''-(benzyloxycarbonyl)benzyl 3,3'-anhydro-4,6-O-benzylidene-3-C-hydroxymethyl-α-D-manno-hexopyranoside (798557-27-4)

Guidance literature:

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 4h;

DOI:10.1021/ol048648u

Reference yield:

2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-α-D-mannopyranoside (365535-43-9) → 2''-(benzyloxycarbonyl)benzyl 3,3'-anhydro-4,6-O-benzylidene-3-C-hydroxymethyl-α-D-manno-hexopyranoside (798557-27-4)

Guidance literature:

Multi-step reaction with 7 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

6.1: 95 percent / Bu₄NF / tetrahydrofuran / 1 h / 20 °C

7.1: 80 percent / m-CPBA; NaHCO₃ / CH₂Cl₂ / 4 h / 0 °C

With 1H-imidazole; n-butyllithium; tetrabutyl ammonium fluoride; di(n-butyl)tin oxide; sodium hydrogencarbonate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; 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

Reference yield:

2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-2-O-tert-butyldimethylsilyl-α-D-arabino-hexopyranosid-3-uloside (798557-24-1) → 2''-(benzyloxycarbonyl)benzyl 3,3'-anhydro-4,6-O-benzylidene-3-C-hydroxymethyl-α-D-manno-hexopyranoside (798557-27-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / n-BuLi / tetrahydrofuran / 5.5 h / 0 °C

2: 95 percent / Bu₄NF / tetrahydrofuran / 1 h / 20 °C

3: 80 percent / m-CPBA; NaHCO₃ / CH₂Cl₂ / 4 h / 0 °C

With n-butyllithium; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol048648u

upstream raw materials:

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

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

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

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

Downstream raw materials:

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