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

Base Information

Chemical Name:2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-2-O-tert-butyldimethylsilyl-α-D-arabino-hexopyranosid-3-uloside
CAS No.:798557-24-1
Molecular Formula:C₃₄H₄₀O₈Si
Molecular Weight:604.772
Hs Code.:

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

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

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

There total 5 articles about 2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-2-O-tert-butyldimethylsilyl-α-D-arabino-hexopyranosid-3-uloside 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%

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

: 798557-24-1
2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-2-O-tert-butyldimethylsilyl-α-D-arabino-hexopyranosid-3-uloside

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 4h;
DOI:10.1021/ol048648u

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 798557-24-1
2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-2-O-tert-butyldimethylsilyl-α-D-arabino-hexopyranosid-3-uloside

Guidance literature:: Multi-step reaction with 3 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

With 1H-imidazole; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; N,N-dimethyl-formamide; 3: Dess-Martin oxidation;
DOI:10.1021/ol048648u

Reference yield:

: 365535-43-9
2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-α-D-mannopyranoside

: 798557-24-1
2'-(benzyloxycarbonyl)benzyl 4,6-O-benzylidene-2-O-tert-butyldimethylsilyl-α-D-arabino-hexopyranosid-3-uloside

Guidance literature:: Multi-step reaction with 4 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

With 1H-imidazole; di(n-butyl)tin oxide; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; water; N,N-dimethyl-formamide; 4.1: Dess-Martin oxidation;
DOI:10.1021/ol048648u