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

Base Information

Chemical Name:(3'S,4'R)-3'-dibenzyloxyphosphoryloxytetrahydrofuran-4'-yl 2,6-di-O-benzyl-3,4-bis-O-(dibenzyloxythiophosphoryl-α-D-glucopyranoside
CAS No.:473441-58-6
Molecular Formula:C₆₆H₆₉O₁₅P₃S₂
Molecular Weight:1259.32
Hs Code.:

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

There total 6 articles about (3'S,4'R)-3'-dibenzyloxyphosphoryloxytetrahydrofuran-4'-yl 2,6-di-O-benzyl-3,4-bis-O-(dibenzyloxythiophosphoryl-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: 84.0%

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

: 473441-57-5
(3'S,4'R)-3'-dibenzyloxyphosphoryloxytetrahydrofuran-4'-yl 2,6-di-O-benzyl-α-D-glucopyranoside

: 473441-58-6
(3'S,4'R)-3'-dibenzyloxyphosphoryloxytetrahydrofuran-4'-yl 2,6-di-O-benzyl-3,4-bis-O-(dibenzyloxythiophosphoryl-α-D-glucopyranoside

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

With pyridine; sulfur; In N,N-dimethyl-formamide; at 20 ℃; for 1h;
DOI:10.1016/S0008-6215(02)00103-9

Reference yield:

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

: 473441-58-6
(3'S,4'R)-3'-dibenzyloxyphosphoryloxytetrahydrofuran-4'-yl 2,6-di-O-benzyl-3,4-bis-O-(dibenzyloxythiophosphoryl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: CH₂Cl₂ / 1 h / 20 °C

1.2: 82 percent / MCPBA / CH₂Cl₂ / -78 - 20 °C

2.1: 64 percent / sat. NH₃ / methanol / 18 h / 20 °C

3.1: 1 H-tetrazole / 1 h / 20 °C

3.2: 84 percent / pyridine; sulfur / dimethylformamide / 1 h / 20 °C

With 1H-tetrazole; ammonia; In methanol; dichloromethane;
DOI:10.1016/S0008-6215(02)00103-9

Reference yield:

: 264230-04-8
3,4-di-O-acetyl-2,6-di-O-benzyl-D-glucopyranosyl dimethyl phosphite

: 473441-58-6
(3'S,4'R)-3'-dibenzyloxyphosphoryloxytetrahydrofuran-4'-yl 2,6-di-O-benzyl-3,4-bis-O-(dibenzyloxythiophosphoryl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 63 percent / 4 Angstroem mol. sieves; ZnCl₂; AgClO₄ / toluene; dioxane / 18 h

2.1: 81 percent / trifluoroacetic acid / CH₂Cl₂ / 0.5 h / 20 °C

3.1: CH₂Cl₂ / 1 h / 20 °C

3.2: 82 percent / MCPBA / CH₂Cl₂ / -78 - 20 °C

4.1: 64 percent / sat. NH₃ / methanol / 18 h / 20 °C

5.1: 1 H-tetrazole / 1 h / 20 °C

5.2: 84 percent / pyridine; sulfur / dimethylformamide / 1 h / 20 °C

With 1H-tetrazole; 4 A molecular sieve; ammonia; silver perchlorate; trifluoroacetic acid; zinc(II) chloride; In 1,4-dioxane; methanol; dichloromethane; toluene;
DOI:10.1016/S0008-6215(02)00103-9