(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

Base Information

• Chemical Name: (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
• CAS No.: 300693-19-0
• Molecular Formula: C₃₁H₄₄O₁₂
• Molecular Weight: 608.683

Synonyms:(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

Chemical Property of (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

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Technology Process of (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

There total 7 articles about (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 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: 75.0%

(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 (300693-17-8) → (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 (300693-19-0)

Guidance literature:

Grubbs catalyst first generation; In toluene; for 16h;

DOI:10.1016/S0040-4020(00)00480-4

Reference yield:

benzyl bromide (100-39-0) → (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 (300693-19-0)

Guidance literature:

Multi-step reaction with 5 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

With trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; sodium hydride; Grubbs catalyst first generation; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide; toluene; 1: Substitution / 2: Substitution / 3: Hydrolysis / 4: Alkylation / 5: Cyclization;

DOI:10.1016/S0040-4020(00)00480-4

Reference yield:

(2'S,3'S)-ethyl 3,4-di-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-β-D-glucopyranoside (197644-79-4) → (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 (300693-19-0)

Guidance literature:

Multi-step reaction with 6 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

With pyridine; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; sodium hydride; Grubbs catalyst first generation; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide; toluene; 1: Substitution / 2: Substitution / 3: Substitution / 4: Hydrolysis / 5: Alkylation / 6: Cyclization;

DOI:10.1016/S0040-4020(00)00480-4

upstream raw materials:

(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

benzyl bromide

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

[(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

Downstream raw materials:

(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

propargyl 2'-O-acetyl-3I-O-(3'',4''-diO-acetyl-2''-O-benzyl-α-D-glucopyranosyl)-5',6''-di-O-(butane-1,4-diyl)-β-D-ribofuranoside

2'-O-acetyl-6-N-benzoyl-5',6''-di-O-(n-butane-1,4-diyl)-3'-O-(3'',4''-di-O-acetyl-2''-O-benzyl-α-D-glucopyranosyl)-adenosine

Phosphoric acid dibenzyl ester (1R,3R,4R,5R,7R,16R,17R,18R,19R)-19-benzyloxy-17,18-bis-(bis-benzyloxy-phosphoryloxy)-5-prop-2-ynyloxy-2,6,9,14,20-pentaoxa-tricyclo[14.3.1.0^3,7]icos-4-yl ester

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