(4R,5R,9R,10R)-1,4-bis(benzyloxy)-11-(tert-butyldimethylsilyloxy)-9,10-(2,2-dimethyl-1,3-dioxolane)-7-(1,3-dithiane)-5-hydroxy-2,2-dimethylundecan-3-one

Base Information

Chemical Name:(4R,5R,9R,10R)-1,4-bis(benzyloxy)-11-(tert-butyldimethylsilyloxy)-9,10-(2,2-dimethyl-1,3-dioxolane)-7-(1,3-dithiane)-5-hydroxy-2,2-dimethylundecan-3-one
CAS No.:1329997-13-8
Molecular Formula:C₃₉H₆₀O₇S₂Si
Molecular Weight:733.119
Hs Code.:

(4R,5R,9R,10R)-1,4-bis(benzyloxy)-11-(tert-butyldimethylsilyloxy)-9,10-(2,2-dimethyl-1,3-dioxolane)-7-(1,3-dithiane)-5-hydroxy-2,2-dimethylundecan-3-one

Synonyms:(4R,5R,9R,10R)-1,4-bis(benzyloxy)-11-(tert-butyldimethylsilyloxy)-9,10-(2,2-dimethyl-1,3-dioxolane)-7-(1,3-dithiane)-5-hydroxy-2,2-dimethylundecan-3-one

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Chemical Property of (4R,5R,9R,10R)-1,4-bis(benzyloxy)-11-(tert-butyldimethylsilyloxy)-9,10-(2,2-dimethyl-1,3-dioxolane)-7-(1,3-dithiane)-5-hydroxy-2,2-dimethylundecan-3-one

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Technology Process of (4R,5R,9R,10R)-1,4-bis(benzyloxy)-11-(tert-butyldimethylsilyloxy)-9,10-(2,2-dimethyl-1,3-dioxolane)-7-(1,3-dithiane)-5-hydroxy-2,2-dimethylundecan-3-one

There total 18 articles about (4R,5R,9R,10R)-1,4-bis(benzyloxy)-11-(tert-butyldimethylsilyloxy)-9,10-(2,2-dimethyl-1,3-dioxolane)-7-(1,3-dithiane)-5-hydroxy-2,2-dimethylundecan-3-one 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%

: 1329997-09-2
(Z)-1,4-dibenzyloxy-3,3-dimethyl-2-(trimethylsilyloxy)-1-butene

: 1329997-12-7
2-(2-{[(4R,5R)-5-{[(tert-butyldimethylsilyl)oxy]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-1,3-dithian-2-yl)acetldehyde

: 1329997-13-8
(4R,5R,9R,10R)-1,4-bis(benzyloxy)-11-(tert-butyldimethylsilyloxy)-9,10-(2,2-dimethyl-1,3-dioxolane)-7-(1,3-dithiane)-5-hydroxy-2,2-dimethylundecan-3-one

Guidance literature:: 2-(2-{[(4R,5R)-5-{[(tert-butyldimethylsilyl)oxy]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-1,3-dithian-2-yl)acetldehyde; With titanium tetrachloride; In dichloromethane; at -78 ℃; for 0.25h; Inert atmosphere;

(Z)-1,4-dibenzyloxy-3,3-dimethyl-2-(trimethylsilyloxy)-1-butene; In dichloromethane; at -78 - -20 ℃; Inert atmosphere;
DOI:10.1002/ejoc.201100053

Reference yield: 25.0%

: 1329997-09-2
(Z)-1,4-dibenzyloxy-3,3-dimethyl-2-(trimethylsilyloxy)-1-butene

: 1329997-12-7
2-(2-{[(4R,5R)-5-{[(tert-butyldimethylsilyl)oxy]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-1,3-dithian-2-yl)acetldehyde

: 1329997-08-1
1,4-dibenzyloxy-3,3-dimethyl-2-butanone

: 1329997-13-8
(4R,5R,9R,10R)-1,4-bis(benzyloxy)-11-(tert-butyldimethylsilyloxy)-9,10-(2,2-dimethyl-1,3-dioxolane)-7-(1,3-dithiane)-5-hydroxy-2,2-dimethylundecan-3-one

Guidance literature:: 2-(2-{[(4R,5R)-5-{[(tert-butyldimethylsilyl)oxy]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-1,3-dithian-2-yl)acetldehyde; With titanium tetrachloride; In dichloromethane; at -78 ℃; Inert atmosphere;

(Z)-1,4-dibenzyloxy-3,3-dimethyl-2-(trimethylsilyloxy)-1-butene; In dichloromethane; at -78 - -20 ℃; Inert atmosphere;
DOI:10.1002/ejoc.201100053

Reference yield:

: 100-39-0
benzyl bromide

: 1329997-13-8
(4R,5R,9R,10R)-1,4-bis(benzyloxy)-11-(tert-butyldimethylsilyloxy)-9,10-(2,2-dimethyl-1,3-dioxolane)-7-(1,3-dithiane)-5-hydroxy-2,2-dimethylundecan-3-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydride / tetrahydrofuran / Inert atmosphere

1.2: Inert atmosphere

2.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

2.2: 1.5 h / -78 - 20 °C / Inert atmosphere

3.1: (-)-(Ipc)2BOTf / dichloromethane / -78 °C / Inert atmosphere

3.2: -78 - -20 °C / Inert atmosphere

With n-butyllithium; (-)-(Ipc)2BOTf; sodium hydride; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1002/ejoc.201100053