methyl 2',5,6'-tri-O-benzyl-3-O-α-D-glucopyranosyl-2,3',4'-tris-O-(dibenzyloxyphosphoryl)-β-D-ribofuranoside

Base Information

Chemical Name:methyl 2',5,6'-tri-O-benzyl-3-O-α-D-glucopyranosyl-2,3',4'-tris-O-(dibenzyloxyphosphoryl)-β-D-ribofuranoside
CAS No.:189151-77-7
Molecular Formula:C₇₅H₇₉O₁₉P₃
Molecular Weight:1377.36
Hs Code.:

Synonyms:methyl 2',5,6'-tri-O-benzyl-3-O-α-D-glucopyranosyl-2,3',4'-tris-O-(dibenzyloxyphosphoryl)-β-D-ribofuranoside

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Chemical Property of methyl 2',5,6'-tri-O-benzyl-3-O-α-D-glucopyranosyl-2,3',4'-tris-O-(dibenzyloxyphosphoryl)-β-D-ribofuranoside

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Technology Process of methyl 2',5,6'-tri-O-benzyl-3-O-α-D-glucopyranosyl-2,3',4'-tris-O-(dibenzyloxyphosphoryl)-β-D-ribofuranoside

There total 8 articles about methyl 2',5,6'-tri-O-benzyl-3-O-α-D-glucopyranosyl-2,3',4'-tris-O-(dibenzyloxyphosphoryl)-β-D-ribofuranoside 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: 89.0%

: 108549-23-1
Dibenzyl N,N-diisopropylphosphoramidite

: 189151-66-4
methyl 2',5,6'-tri-O-benzyl-3-O-α-D-glucopyranosyl-β-D-ribofuranoside

: 189151-77-7
methyl 2',5,6'-tri-O-benzyl-3-O-α-D-glucopyranosyl-2,3',4'-tris-O-(dibenzyloxyphosphoryl)-β-D-ribofuranoside

Guidance literature:: With 1H-tetrazole; In dichloromethane; at 20 ℃; for 0.5h;
DOI:10.1016/S0008-6215(02)00103-9

Reference yield:

: 100-39-0
benzyl bromide

: 189151-77-7
methyl 2',5,6'-tri-O-benzyl-3-O-α-D-glucopyranosyl-2,3',4'-tris-O-(dibenzyloxyphosphoryl)-β-D-ribofuranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 81 percent / NaH (in oil) / dimethylformamide / 2.5 h / 20 °C

2: 43 percent / DIBAL-H / CH₂Cl₂ / 1.67 h / -78 - 0 °C

3: 4 Angstroem mol. sieves; trimethylsilyl triflate / diethyl ether / 0.58 h / 20 °C

4: DDQ / CH₂Cl₂; H₂O / 1 h

5: 89 percent / 1H-tetrazole / CH₂Cl₂ / 0.5 h / 20 °C

With 1H-tetrazole; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium hydride; diisobutylaluminium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(02)00103-9

Reference yield:

: 33981-58-7
methyl 2,3-O-p-methoxybenzylidene-β-D-ribofuranoside

: 189151-77-7
methyl 2',5,6'-tri-O-benzyl-3-O-α-D-glucopyranosyl-2,3',4'-tris-O-(dibenzyloxyphosphoryl)-β-D-ribofuranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 81 percent / NaH (in oil) / dimethylformamide / 2.5 h / 20 °C

2: 43 percent / DIBAL-H / CH₂Cl₂ / 1.67 h / -78 - 0 °C

3: 4 Angstroem mol. sieves; trimethylsilyl triflate / diethyl ether / 0.58 h / 20 °C

4: DDQ / CH₂Cl₂; H₂O / 1 h

5: 89 percent / 1H-tetrazole / CH₂Cl₂ / 0.5 h / 20 °C

With 1H-tetrazole; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium hydride; diisobutylaluminium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(02)00103-9