5-O-allyl-1,2,3-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-4-O-diphenoxyphosphoryl-β-D-glucopyranosyl)-D-ribitol

Base Information

Chemical Name:5-O-allyl-1,2,3-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-4-O-diphenoxyphosphoryl-β-D-glucopyranosyl)-D-ribitol
CAS No.:116490-83-6
Molecular Formula:C₆₈H₇₁O₁₃P
Molecular Weight:1127.28
Hs Code.:

Synonyms:5-O-allyl-1,2,3-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-4-O-diphenoxyphosphoryl-β-D-glucopyranosyl)-D-ribitol

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Chemical Property of 5-O-allyl-1,2,3-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-4-O-diphenoxyphosphoryl-β-D-glucopyranosyl)-D-ribitol

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Technology Process of 5-O-allyl-1,2,3-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-4-O-diphenoxyphosphoryl-β-D-glucopyranosyl)-D-ribitol

There total 7 articles about 5-O-allyl-1,2,3-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-4-O-diphenoxyphosphoryl-β-D-glucopyranosyl)-D-ribitol 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:

: 100-39-0
benzyl bromide

: 116490-83-6
5-O-allyl-1,2,3-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-4-O-diphenoxyphosphoryl-β-D-glucopyranosyl)-D-ribitol

Guidance literature:: Multi-step reaction with 4 steps

1: 70 percent / sodium hydride 50 percent disp. in oil / dimethylformamide / 1.5 h / Ambient temperature

2: 80 percent / Dowex 50W-X₄ (H+) resin / methanol / 6 h / Heating

3: 49 percent / aqueous 5percent sodium hydroxide, tetrabutylammonium bromide / CH₂Cl₂ / 19 h / Heating

4: 1.) 1,2,4-triazole, triethylamine, oxolane; 2.) 4-dimethylaminopyridine / 1.) 10 min at 10 deg C, 45 min at R_.T_.; 2.) pyridine, 1.5 h at 40 deg C

With tetrahydrofuran; 1,2,4-Triazole; dmap; sodium hydroxide; Dowex 50W-X₄ (H+) resin; tetrabutylammomium bromide; sodium hydride; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(88)84144-2

Reference yield:

: 116490-77-8
2,3-di-O-acetyl-4,6-O-ethylidene-α-D-glucopyranosyl bromide

: 116490-83-6
5-O-allyl-1,2,3-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-4-O-diphenoxyphosphoryl-β-D-glucopyranosyl)-D-ribitol

Guidance literature:: Multi-step reaction with 5 steps

1: 86 percent / mercuric bromode, mercuric cyanide, pulverised molecular sieves (3 A) / benzene; nitromethane

2: 70 percent / sodium hydride 50 percent disp. in oil / dimethylformamide / 1.5 h / Ambient temperature

3: 80 percent / Dowex 50W-X₄ (H+) resin / methanol / 6 h / Heating

4: 49 percent / aqueous 5percent sodium hydroxide, tetrabutylammonium bromide / CH₂Cl₂ / 19 h / Heating

5: 1.) 1,2,4-triazole, triethylamine, oxolane; 2.) 4-dimethylaminopyridine / 1.) 10 min at 10 deg C, 45 min at R_.T_.; 2.) pyridine, 1.5 h at 40 deg C

With tetrahydrofuran; 1,2,4-Triazole; dmap; sodium hydroxide; 3 A molecular sieve; Dowex 50W-X₄ (H+) resin; tetrabutylammomium bromide; mercury(II) cyanide; sodium hydride; triethylamine; mercury dibromide; In methanol; nitromethane; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1016/0008-6215(88)84144-2

Reference yield:

: 116490-78-9
5-O-allyl-1,2,3-tri-O-benzyl-4-O-(2,3-di-O-acetyl-4,6-O-ethylidene-β-D-glucopyranosyl)-D-ribitol

: 116490-83-6
5-O-allyl-1,2,3-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-4-O-diphenoxyphosphoryl-β-D-glucopyranosyl)-D-ribitol

Guidance literature:: Multi-step reaction with 4 steps

1: 70 percent / sodium hydride 50 percent disp. in oil / dimethylformamide / 1.5 h / Ambient temperature

2: 80 percent / Dowex 50W-X₄ (H+) resin / methanol / 6 h / Heating

3: 49 percent / aqueous 5percent sodium hydroxide, tetrabutylammonium bromide / CH₂Cl₂ / 19 h / Heating

4: 1.) 1,2,4-triazole, triethylamine, oxolane; 2.) 4-dimethylaminopyridine / 1.) 10 min at 10 deg C, 45 min at R_.T_.; 2.) pyridine, 1.5 h at 40 deg C

With tetrahydrofuran; 1,2,4-Triazole; dmap; sodium hydroxide; Dowex 50W-X₄ (H+) resin; tetrabutylammomium bromide; sodium hydride; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(88)84144-2