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

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Chemical Name:(2''S,3''S) 3-O-(2'-O-benzyl-3',4'-di-O-(2'',3''-dimethoxybutane-2'',3''-diyl)-α-D-glucopyranosyl)-5,6'-di-O-(butane-1,4-diyl)-1,2-O-isopropylidene-α-D-ribofuranoside
CAS No.:300693-20-3
Molecular Formula:C₃₁H₄₆O₁₂
Molecular Weight:610.699
Hs Code.:

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

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

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

There total 8 articles about (2''S,3''S) 3-O-(2'-O-benzyl-3',4'-di-O-(2'',3''-dimethoxybutane-2'',3''-diyl)-α-D-glucopyranosyl)-5,6'-di-O-(butane-1,4-diyl)-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:

: 300693-19-0
(E/Z, 2''S,3''S) 5,6'-di-O-but-2-en-1,4-diyl-3-O-(2'-O-benzyl-3',4'-di-O-(2'',3''-dimethoxybutane-2'',3''-diyl)-α-D-glucopyranosyl)-1,2-O-isopropylidene-α-D-ribofuranoside

: 300693-20-3
(2''S,3''S) 3-O-(2'-O-benzyl-3',4'-di-O-(2'',3''-dimethoxybutane-2'',3''-diyl)-α-D-glucopyranosyl)-5,6'-di-O-(butane-1,4-diyl)-1,2-O-isopropylidene-α-D-ribofuranoside

Guidance literature:: With hydrogen; platinum(IV) oxide; In ethyl acetate;
DOI:10.1016/S0040-4020(00)00480-4

Reference yield:

: 100-39-0
benzyl bromide

: 300693-20-3
(2''S,3''S) 3-O-(2'-O-benzyl-3',4'-di-O-(2'',3''-dimethoxybutane-2'',3''-diyl)-α-D-glucopyranosyl)-5,6'-di-O-(butane-1,4-diyl)-1,2-O-isopropylidene-α-D-ribofuranoside

Guidance literature:: Multi-step reaction with 6 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

5: 75 percent / RuCl₂(PCy₃)2CHPh / toluene / 16 h

6: 0.21 g / H₂ / PtO₂ / ethyl acetate

With trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; Grubbs catalyst first generation; platinum(IV) oxide; In tetrahydrofuran; 1,4-dioxane; ethyl acetate; N,N-dimethyl-formamide; toluene; 1: Substitution / 2: Substitution / 3: Hydrolysis / 4: Alkylation / 5: Cyclization / 6: Catalytic hydrogenation;
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

: 300693-20-3
(2''S,3''S) 3-O-(2'-O-benzyl-3',4'-di-O-(2'',3''-dimethoxybutane-2'',3''-diyl)-α-D-glucopyranosyl)-5,6'-di-O-(butane-1,4-diyl)-1,2-O-isopropylidene-α-D-ribofuranoside

Guidance literature:: Multi-step reaction with 7 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

6: 75 percent / RuCl₂(PCy₃)2CHPh / toluene / 16 h

7: 0.21 g / H₂ / PtO₂ / ethyl acetate

With pyridine; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; Grubbs catalyst first generation; platinum(IV) oxide; In tetrahydrofuran; 1,4-dioxane; ethyl acetate; N,N-dimethyl-formamide; toluene; 1: Substitution / 2: Substitution / 3: Substitution / 4: Hydrolysis / 5: Alkylation / 6: Cyclization / 7: Catalytic hydrogenation;
DOI:10.1016/S0040-4020(00)00480-4