(2S,3S,5R,6R,1'S,2'R,2''R,3''R)-5-[2'-(3'',4''-bis(benzyloxy)-2''-methylbutyl)-1'-methoxymethoxybut-3'-enyl]-2,3-dimethoxy-2,3-dimethyl-6-vinyl[1,4]dioxane

Base Information

Chemical Name:(2S,3S,5R,6R,1'S,2'R,2''R,3''R)-5-[2'-(3'',4''-bis(benzyloxy)-2''-methylbutyl)-1'-methoxymethoxybut-3'-enyl]-2,3-dimethoxy-2,3-dimethyl-6-vinyl[1,4]dioxane
CAS No.:856190-76-6
Molecular Formula:C₃₅H₅₀O₈
Molecular Weight:598.777
Hs Code.:

Synonyms:(2S,3S,5R,6R,1'S,2'R,2''R,3''R)-5-[2'-(3'',4''-bis(benzyloxy)-2''-methylbutyl)-1'-methoxymethoxybut-3'-enyl]-2,3-dimethoxy-2,3-dimethyl-6-vinyl[1,4]dioxane

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Chemical Property of (2S,3S,5R,6R,1'S,2'R,2''R,3''R)-5-[2'-(3'',4''-bis(benzyloxy)-2''-methylbutyl)-1'-methoxymethoxybut-3'-enyl]-2,3-dimethoxy-2,3-dimethyl-6-vinyl[1,4]dioxane

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Technology Process of (2S,3S,5R,6R,1'S,2'R,2''R,3''R)-5-[2'-(3'',4''-bis(benzyloxy)-2''-methylbutyl)-1'-methoxymethoxybut-3'-enyl]-2,3-dimethoxy-2,3-dimethyl-6-vinyl[1,4]dioxane

There total 6 articles about (2S,3S,5R,6R,1'S,2'R,2''R,3''R)-5-[2'-(3'',4''-bis(benzyloxy)-2''-methylbutyl)-1'-methoxymethoxybut-3'-enyl]-2,3-dimethoxy-2,3-dimethyl-6-vinyl[1,4]dioxane 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:

: 856190-83-5
(2R,3R,5S,6S,1'S,2'R,2''R,3''R)-{3-[2'-(3'',4''-bis(benzyloxy)-2''-methylbutyl)-1'-methoxymethoxybut-3'-enyl]-5,6-dimethoxy-5,6-dimethyl[1,4]dioxan-2-yl}methanol

: 856190-76-6
(2S,3S,5R,6R,1'S,2'R,2''R,3''R)-5-[2'-(3'',4''-bis(benzyloxy)-2''-methylbutyl)-1'-methoxymethoxybut-3'-enyl]-2,3-dimethoxy-2,3-dimethyl-6-vinyl[1,4]dioxane

Guidance literature:: Multi-step reaction with 2 steps

1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 20 °C

2: 87 percent / n-BuLi / hexane; tetrahydrofuran / 12 h / -78 - 20 °C

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 1: Swern oxidation / 2: Wittig olefination;
DOI:10.1002/anie.200500174

Reference yield:

: 856190-82-4
(1S,2R)-2-((2R,3R)-3,4-dibenzyloxy-2-methylbutyl)-1-[(2R,3R,5S,6S)-3-(tert-butyldimethylsilanyloxymethyl)-5,6-dimethoxy-5,6-dimethyl[1,4]dioxan-2-yl]but-3-en-1-ol

: 856190-76-6
(2S,3S,5R,6R,1'S,2'R,2''R,3''R)-5-[2'-(3'',4''-bis(benzyloxy)-2''-methylbutyl)-1'-methoxymethoxybut-3'-enyl]-2,3-dimethoxy-2,3-dimethyl-6-vinyl[1,4]dioxane

Guidance literature:: Multi-step reaction with 3 steps

1.1: iPr₂NEt / CH₂Cl₂ / 20 h / -5 °C

1.2: 89 percent / TBAF / tetrahydrofuran / 1.5 h / 0 °C

2.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: 87 percent / n-BuLi / hexane; tetrahydrofuran / 12 h / -78 - 20 °C

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; 2.1: Swern oxidation / 3.1: Wittig olefination;
DOI:10.1002/anie.200500174

Reference yield:

: 241811-65-4
(2S,3S,5S,6S)-5,6-dimethoxy-5,6-dimethyl[1,4]dioxane-2,3-dicarboxylic acid dimethyl ester

: 856190-76-6
(2S,3S,5R,6R,1'S,2'R,2''R,3''R)-5-[2'-(3'',4''-bis(benzyloxy)-2''-methylbutyl)-1'-methoxymethoxybut-3'-enyl]-2,3-dimethoxy-2,3-dimethyl-6-vinyl[1,4]dioxane

Guidance literature:: Multi-step reaction with 7 steps

1.1: 78 percent / LiAlH₄ / tetrahydrofuran / 20 h / 20 °C

2.1: 86 percent / NaH / tetrahydrofuran / 15 h / 20 °C

3.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 20 °C

4.1: 76 percent / ZnI₂ / CH₂Cl₂ / 42 h / -20 - 20 °C

5.1: iPr₂NEt / CH₂Cl₂ / 20 h / -5 °C

5.2: 89 percent / TBAF / tetrahydrofuran / 1.5 h / 0 °C

6.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 20 °C

7.1: 87 percent / n-BuLi / hexane; tetrahydrofuran / 12 h / -78 - 20 °C

With lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; zinc(II) iodide; In tetrahydrofuran; hexane; dichloromethane; 3.1: Swern oxidation / 6.1: Swern oxidation / 7.1: Wittig olefination;
DOI:10.1002/anie.200500174