(2''S,3''S) 5-O-allyl-3-O-(6'-O-allyl-2'-O-benzyl-3',4'-di-O-(2'',3''-dimethoxybutane-2'',3''-diyl)-α-D-glucopyranosyl)-1,2-O-isopropylidene-α-D-ribofuranoside

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Chemical Name:(2''S,3''S) 5-O-allyl-3-O-(6'-O-allyl-2'-O-benzyl-3',4'-di-O-(2'',3''-dimethoxybutane-2'',3''-diyl)-α-D-glucopyranosyl)-1,2-O-isopropylidene-α-D-ribofuranoside
CAS No.:300693-17-8
Molecular Formula:C₃₃H₄₈O₁₂
Molecular Weight:636.737
Hs Code.:

Synonyms:(2''S,3''S) 5-O-allyl-3-O-(6'-O-allyl-2'-O-benzyl-3',4'-di-O-(2'',3''-dimethoxybutane-2'',3''-diyl)-α-D-glucopyranosyl)-1,2-O-isopropylidene-α-D-ribofuranoside

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Chemical Property of (2''S,3''S) 5-O-allyl-3-O-(6'-O-allyl-2'-O-benzyl-3',4'-di-O-(2'',3''-dimethoxybutane-2'',3''-diyl)-α-D-glucopyranosyl)-1,2-O-isopropylidene-α-D-ribofuranoside

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Technology Process of (2''S,3''S) 5-O-allyl-3-O-(6'-O-allyl-2'-O-benzyl-3',4'-di-O-(2'',3''-dimethoxybutane-2'',3''-diyl)-α-D-glucopyranosyl)-1,2-O-isopropylidene-α-D-ribofuranoside

There total 6 articles about (2''S,3''S) 5-O-allyl-3-O-(6'-O-allyl-2'-O-benzyl-3',4'-di-O-(2'',3''-dimethoxybutane-2'',3''-diyl)-α-D-glucopyranosyl)-1,2-O-isopropylidene-α-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%

: 106-95-6
allyl bromide

: 300693-14-5
[(2S,3S,4aR,5R,7R,8R,8aS)-8-Benzyloxy-7-((3aR,5R,6R,6aR)-5-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy)-2,3-dimethoxy-2,3-dimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-5-yl]-methanol

: 300693-17-8
(2''S,3''S) 5-O-allyl-3-O-(6'-O-allyl-2'-O-benzyl-3',4'-di-O-(2'',3''-dimethoxybutane-2'',3''-diyl)-α-D-glucopyranosyl)-1,2-O-isopropylidene-α-D-ribofuranoside

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; for 3h; cooling;
DOI:10.1016/S0040-4020(00)00480-4

Reference yield:

: 100-39-0
benzyl bromide

: 300693-17-8
(2''S,3''S) 5-O-allyl-3-O-(6'-O-allyl-2'-O-benzyl-3',4'-di-O-(2'',3''-dimethoxybutane-2'',3''-diyl)-α-D-glucopyranosyl)-1,2-O-isopropylidene-α-D-ribofuranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 4.40 g / NaH / dimethylformamide / 0 °C

2: 74 percent / TfOH / toluene; dioxane / 0.25 h

3: 95 percent / TBAF / tetrahydrofuran; dioxane / 16 h / 50 °C

4: 89 percent / sodium hydride / dimethylformamide / 3 h / cooling

With trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide; toluene; 1: Substitution / 2: Substitution / 3: Hydrolysis / 4: Alkylation;
DOI:10.1016/S0040-4020(00)00480-4

Reference yield:

: 197644-79-4
(2'S,3'S)-ethyl 3,4-di-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-β-D-glucopyranoside

: 300693-17-8
(2''S,3''S) 5-O-allyl-3-O-(6'-O-allyl-2'-O-benzyl-3',4'-di-O-(2'',3''-dimethoxybutane-2'',3''-diyl)-α-D-glucopyranosyl)-1,2-O-isopropylidene-α-D-ribofuranoside

Guidance literature:: Multi-step reaction with 5 steps

1: pyridine / 2 h

2: 4.40 g / NaH / dimethylformamide / 0 °C

3: 74 percent / TfOH / toluene; dioxane / 0.25 h

4: 95 percent / TBAF / tetrahydrofuran; dioxane / 16 h / 50 °C

5: 89 percent / sodium hydride / dimethylformamide / 3 h / cooling

With pyridine; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide; toluene; 1: Substitution / 2: Substitution / 3: Substitution / 4: Hydrolysis / 5: Alkylation;
DOI:10.1016/S0040-4020(00)00480-4