(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

Base Information

Chemical Name:(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
CAS No.:856190-83-5
Molecular Formula:C₃₄H₅₀O₉
Molecular Weight:602.766
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 5 articles about (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 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%

: 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

: 107-30-2
chloromethyl methyl ether

: 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

Guidance literature:: (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; chloromethyl methyl ether; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -5 ℃; for 20h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 1.5h;
DOI:10.1002/anie.200500174

Reference yield:

: 241811-69-8
(2S,3R,5S,6S)-3-(tert-butyldimethylsilanyloxymethyl)-5,6-dimethoxy-5,6-dimethyl[1,4]dioxane-2-carbaldehyde

: 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

Guidance literature:: Multi-step reaction with 2 steps

1.1: 76 percent / ZnI₂ / CH₂Cl₂ / 42 h / -20 - 20 °C

2.1: iPr₂NEt / CH₂Cl₂ / 20 h / -5 °C

2.2: 89 percent / TBAF / tetrahydrofuran / 1.5 h / 0 °C

With N-ethyl-N,N-diisopropylamine; zinc(II) iodide; In dichloromethane;
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

: 856190-83-5
(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

Guidance literature:: Multi-step reaction with 5 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

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