(2S,5R,6R,9R,10R)-10-(tert-butyldimethylsilyloxy)-2,5-dihydroxy-6,9-epoxydocosanyl 2,4,6-triisopropylbenzenesulfonate

Base Information

Chemical Name:(2S,5R,6R,9R,10R)-10-(tert-butyldimethylsilyloxy)-2,5-dihydroxy-6,9-epoxydocosanyl 2,4,6-triisopropylbenzenesulfonate
CAS No.:532384-81-9
Molecular Formula:C₄₃H₈₀O₇SSi
Molecular Weight:769.255
Hs Code.:

Synonyms:(2S,5R,6R,9R,10R)-10-(tert-butyldimethylsilyloxy)-2,5-dihydroxy-6,9-epoxydocosanyl 2,4,6-triisopropylbenzenesulfonate

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Chemical Property of (2S,5R,6R,9R,10R)-10-(tert-butyldimethylsilyloxy)-2,5-dihydroxy-6,9-epoxydocosanyl 2,4,6-triisopropylbenzenesulfonate

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Technology Process of (2S,5R,6R,9R,10R)-10-(tert-butyldimethylsilyloxy)-2,5-dihydroxy-6,9-epoxydocosanyl 2,4,6-triisopropylbenzenesulfonate

There total 4 articles about (2S,5R,6R,9R,10R)-10-(tert-butyldimethylsilyloxy)-2,5-dihydroxy-6,9-epoxydocosanyl 2,4,6-triisopropylbenzenesulfonate 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: 71.0%

: 6553-96-4
2,4,6-triisopropylphenylsulfonyl chloride

: 532384-80-8
(2S,5R,6R,9R,10R)-10-(tert-butyldimethylsilyloxy)-6,9-epoxydocosane-1,2,5-triol

: 532384-81-9
(2S,5R,6R,9R,10R)-10-(tert-butyldimethylsilyloxy)-2,5-dihydroxy-6,9-epoxydocosanyl 2,4,6-triisopropylbenzenesulfonate

Guidance literature:: With pyridine; In dichloromethane; at 0 - 20 ℃;
DOI:10.1021/ol034131r

Reference yield:

: 163730-22-1
(2R,5R)-5-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-tridecyl]-tetrahydro-furan-2-carbaldehyde

: 532384-81-9
(2S,5R,6R,9R,10R)-10-(tert-butyldimethylsilyloxy)-2,5-dihydroxy-6,9-epoxydocosanyl 2,4,6-triisopropylbenzenesulfonate

Guidance literature:: Multi-step reaction with 3 steps

1.1: Zn(OTf)2; (1S,2R)-N-methylephedrine; Et₃N / toluene / 0.25 h / 20 °C

1.2: toluene / 19 h / 20 °C

2.1: 76 percent / H₂ / Pd/C / ethyl acetate / 19 h / 20 °C

3.1: 71 percent / CH₂Cl₂; pyridine / 21 h / 20 °C

With (1S,2R)-(+)-N-methylephedrine; hydrogen; zinc trifluoromethanesulfonate; triethylamine; palladium on activated charcoal; In pyridine; dichloromethane; ethyl acetate; toluene;
DOI:10.1002/chem.200305459

Reference yield:

: 532384-79-5
(2RS,4S)-4-[(3'R,4'R,7'R,8'R)-8'-(tert-butyldimethylsilyloxy)-3'-hydroxy-4',7'-epoxy-1'-icosynyl]-2-phenyl-1,3-dioxolane

: 532384-81-9
(2S,5R,6R,9R,10R)-10-(tert-butyldimethylsilyloxy)-2,5-dihydroxy-6,9-epoxydocosanyl 2,4,6-triisopropylbenzenesulfonate

Guidance literature:: Multi-step reaction with 2 steps

1: 76 percent / H₂ / Pd/C / ethyl acetate / 19 h / 20 °C

2: 71 percent / CH₂Cl₂; pyridine / 21 h / 20 °C

With hydrogen; palladium on activated charcoal; In pyridine; dichloromethane; ethyl acetate;
DOI:10.1002/chem.200305459