(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

Base Information

• Chemical Name: (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
• CAS No.: 856190-82-4
• Molecular Formula: C₃₈H₆₀O₈Si
• Molecular Weight: 672.975

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (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

There total 5 articles about (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 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: 76.0%

(5R,6R)-tributyl(6,7-dibenzyloxy-5-methylhept-2-enyl)stannane + (2S,3R,5S,6S)-3-(tert-butyldimethylsilanyloxymethyl)-5,6-dimethoxy-5,6-dimethyl[1,4]dioxane-2-carbaldehyde (241811-69-8) → (1S,2S)-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 + (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 (856190-82-4)

Guidance literature:

With zinc(II) iodide; In dichloromethane; at -20 - 20 ℃; for 42h;

DOI:10.1002/anie.200500174

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (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 (856190-82-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / NaH / tetrahydrofuran / 15 h / 20 °C

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

3: 76 percent / ZnI₂ / CH₂Cl₂ / 42 h / -20 - 20 °C

With oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; zinc(II) iodide; In tetrahydrofuran; dichloromethane; 2: Swern oxidation;

DOI:10.1002/anie.200500174

Reference yield:

(2R,3R,5S,6S)-(3-hydroxymethyl-5,6-dimethoxy-5,6-dimethyl[1,4]dioxan-2-yl)methanol (241811-66-5) → (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 (856190-82-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / NaH / tetrahydrofuran / 15 h / 20 °C

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

3: 76 percent / ZnI₂ / CH₂Cl₂ / 42 h / -20 - 20 °C

With oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; zinc(II) iodide; In tetrahydrofuran; dichloromethane; 2: Swern oxidation;

DOI:10.1002/anie.200500174

upstream raw materials:

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

tert-butyldimethylsilyl chloride

(2R,3R,5S,6S)-(3-hydroxymethyl-5,6-dimethoxy-5,6-dimethyl[1,4]dioxan-2-yl)methanol

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

Downstream raw materials:

(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

C₆₃H₁₀₉NO₁₅Si₂

C₆₃H₁₀₇NO₁₄Si₂

(7E,11E,2R,3S,6R,13R,14R,15S,18R,2'S,3'S,4a'S,5'S,6'S,8a'R)-5-benzenesulfonyl-13,15,19-tris(tert-butyldimethylsilyloxy)-1-(2',3'-dimethoxy-5'-methoxymethoxy-2',3'-dimethyloctahydrobenzo[1',4']dioxin-6'-yl)-2,6,14,18,-tetramethylnonadeca-7,11-dien-3-ol

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