(3'S,4'R)-3'-dibenzyloxyphosphoryloxytetrahydrofuran-4'-yl 2,6-di-O-benzyl-3,4-bis-O-(dibenzyloxyphosphoryl)-α-D-glucopyranoside

Base Information

Chemical Name:(3'S,4'R)-3'-dibenzyloxyphosphoryloxytetrahydrofuran-4'-yl 2,6-di-O-benzyl-3,4-bis-O-(dibenzyloxyphosphoryl)-α-D-glucopyranoside
CAS No.:219530-53-7
Molecular Formula:C₆₆H₆₉O₁₇P₃
Molecular Weight:1227.18
Hs Code.:

Synonyms:(3'S,4'R)-3'-dibenzyloxyphosphoryloxytetrahydrofuran-4'-yl 2,6-di-O-benzyl-3,4-bis-O-(dibenzyloxyphosphoryl)-α-D-glucopyranoside

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Chemical Property of (3'S,4'R)-3'-dibenzyloxyphosphoryloxytetrahydrofuran-4'-yl 2,6-di-O-benzyl-3,4-bis-O-(dibenzyloxyphosphoryl)-α-D-glucopyranoside

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Technology Process of (3'S,4'R)-3'-dibenzyloxyphosphoryloxytetrahydrofuran-4'-yl 2,6-di-O-benzyl-3,4-bis-O-(dibenzyloxyphosphoryl)-α-D-glucopyranoside

There total 13 articles about (3'S,4'R)-3'-dibenzyloxyphosphoryloxytetrahydrofuran-4'-yl 2,6-di-O-benzyl-3,4-bis-O-(dibenzyloxyphosphoryl)-α-D-glucopyranoside 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: 98.0%

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

: 221356-66-7
(3'S,4'R)-3'-hydroxytetrahydrofuran-4'-yl 2,6-di-O-benzyl-α-D-glucopyranoside

: 219530-53-7
(3'S,4'R)-3'-dibenzyloxyphosphoryloxytetrahydrofuran-4'-yl 2,6-di-O-benzyl-3,4-bis-O-(dibenzyloxyphosphoryl)-α-D-glucopyranoside

Guidance literature:: Dibenzyl N,N-diisopropylphosphoramidite; (3'S,4'R)-3'-hydroxytetrahydrofuran-4'-yl 2,6-di-O-benzyl-α-D-glucopyranoside; With 1H-tetrazole; In dichloromethane; at 20 ℃; for 0.5h;

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 - 20 ℃;
DOI:10.1016/S0008-6215(02)00103-9

Reference yield:

: 6-O-acetyl-3,4-di-O-allyl-2-O-benzyl-D-glucopyranose

: 219530-53-7
(3'S,4'R)-3'-dibenzyloxyphosphoryloxytetrahydrofuran-4'-yl 2,6-di-O-benzyl-3,4-bis-O-(dibenzyloxyphosphoryl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 93 percent / DAST / CH₂Cl₂ / 2 h / 0 °C

2: 78 percent / TMSOTf, Et₃N / diethyl ether / 1.5 h / Ambient temperature

4: aq. p-TsOH / Pd/C / ethanol / 4 h / Heating

5: 1.) tetrazole, 2.) aq. m-CPBA / 1.) CH₂Cl₂, room temperature, 7 h, 2.) CH₂Cl₂, room temperature, 2 h

With 1H-tetrazole; trimethylsilyl trifluoromethanesulfonate; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; 4,4'-diaminostilbene-2,2'-disulfonic acid; palladium on activated charcoal; In diethyl ether; ethanol; dichloromethane;
DOI:10.1021/jo980925l

Reference yield:

: 211630-26-1
6-O-acetyl-3,4-di-O-allyl-2-O-benzyl-D-glucopyranosyl fluoride

: 219530-53-7
(3'S,4'R)-3'-dibenzyloxyphosphoryloxytetrahydrofuran-4'-yl 2,6-di-O-benzyl-3,4-bis-O-(dibenzyloxyphosphoryl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 78 percent / TMSOTf, Et₃N / diethyl ether / 1.5 h / Ambient temperature

3: aq. p-TsOH / Pd/C / ethanol / 4 h / Heating

4: 1.) tetrazole, 2.) aq. m-CPBA / 1.) CH₂Cl₂, room temperature, 7 h, 2.) CH₂Cl₂, room temperature, 2 h

With 1H-tetrazole; trimethylsilyl trifluoromethanesulfonate; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In diethyl ether; ethanol;
DOI:10.1021/jo980925l