(S)-12-[(4R,5S)-5-{(R)-2-(benzyloxy)-1-(tert-butyldimethylsilyloxy)-ethyl}-2,2-dimethyl-1,3-dioxolan-4-yl]dodec-11-yn-2-ol

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Chemical Name:(S)-12-[(4R,5S)-5-{(R)-2-(benzyloxy)-1-(tert-butyldimethylsilyloxy)-ethyl}-2,2-dimethyl-1,3-dioxolan-4-yl]dodec-11-yn-2-ol
CAS No.:1374433-38-1
Molecular Formula:C₃₂H₅₄O₅Si
Molecular Weight:546.863
Hs Code.:

Synonyms:(S)-12-[(4R,5S)-5-{(R)-2-(benzyloxy)-1-(tert-butyldimethylsilyloxy)-ethyl}-2,2-dimethyl-1,3-dioxolan-4-yl]dodec-11-yn-2-ol

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Chemical Property of (S)-12-[(4R,5S)-5-{(R)-2-(benzyloxy)-1-(tert-butyldimethylsilyloxy)-ethyl}-2,2-dimethyl-1,3-dioxolan-4-yl]dodec-11-yn-2-ol

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Technology Process of (S)-12-[(4R,5S)-5-{(R)-2-(benzyloxy)-1-(tert-butyldimethylsilyloxy)-ethyl}-2,2-dimethyl-1,3-dioxolan-4-yl]dodec-11-yn-2-ol

There total 9 articles about (S)-12-[(4R,5S)-5-{(R)-2-(benzyloxy)-1-(tert-butyldimethylsilyloxy)-ethyl}-2,2-dimethyl-1,3-dioxolan-4-yl]dodec-11-yn-2-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: 88.0%

: 1374433-35-8
(2S,13R,14S,15R)-16-(benzyloxy)-15-(tert-butyldimethylsilyloxy)hexadec-11-yne-2,13,14-triol

: 77-76-9
2,2-dimethoxy-propane

: 1374433-38-1
(S)-12-[(4R,5S)-5-{(R)-2-(benzyloxy)-1-(tert-butyldimethylsilyloxy)-ethyl}-2,2-dimethyl-1,3-dioxolan-4-yl]dodec-11-yn-2-ol

Guidance literature:: With camphor-10-sulfonic acid; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1002/ejoc.201101673

Reference yield:

: 140461-17-2
(S)-dodec-4-yn-2-ol

: 1374433-38-1
(S)-12-[(4R,5S)-5-{(R)-2-(benzyloxy)-1-(tert-butyldimethylsilyloxy)-ethyl}-2,2-dimethyl-1,3-dioxolan-4-yl]dodec-11-yn-2-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: potassium hydride; Trimethylenediamine / diethyl ether; mineral oil / 15 h / 0 - 20 °C / Inert atmosphere

2.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 0.25 h / 0 °C

2.2: 2.67 h / 0 - 20 °C

3.1: AD-mix β; methanesulfonamide / water; tert-butyl alcohol / 72 h / 0 °C

4.1: camphor-10-sulfonic acid / dichloromethane / 1 h / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; methanesulfonamide; AD-mix β; camphor-10-sulfonic acid; potassium hydride; Trimethylenediamine; triethylamine; In diethyl ether; dichloromethane; water; mineral oil; tert-butyl alcohol; 1.1: Zipper reaction / 2.1: Sonogashira coupling / 2.2: Sonogashira coupling / 3.1: Sharpless dihydroxylation;
DOI:10.1002/ejoc.201101673

Reference yield:

: 1374578-16-1
(S)-[1-(benzyloxy)but-3-yn-2-yloxy](tert-butyl)dimethylsilane

: 1374433-38-1
(S)-12-[(4R,5S)-5-{(R)-2-(benzyloxy)-1-(tert-butyldimethylsilyloxy)-ethyl}-2,2-dimethyl-1,3-dioxolan-4-yl]dodec-11-yn-2-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: zirconocene dichloride; lithium triethylborohydride / tetrahydrofuran / 0.5 h / 20 °C

1.2: 0.5 h / 0 °C

2.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 0.25 h / 0 °C

2.2: 2.67 h / 0 - 20 °C

3.1: AD-mix β; methanesulfonamide / water; tert-butyl alcohol / 72 h / 0 °C

4.1: camphor-10-sulfonic acid / dichloromethane / 1 h / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; zirconocene dichloride; methanesulfonamide; AD-mix β; camphor-10-sulfonic acid; lithium triethylborohydride; triethylamine; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol; 2.1: Sonogashira coupling / 2.2: Sonogashira coupling / 3.1: Sharpless dihydroxylation;
DOI:10.1002/ejoc.201101673