(3S,4S,5R)-6-(tert-butyldimethylsiloxy)-4-(4-methoxybenzyloxy)-5-methylhex-1-en-3-ol

Base Information

Chemical Name:(3S,4S,5R)-6-(tert-butyldimethylsiloxy)-4-(4-methoxybenzyloxy)-5-methylhex-1-en-3-ol
CAS No.:910215-33-7
Molecular Formula:C₂₁H₃₆O₄Si
Molecular Weight:380.6
Hs Code.:

Synonyms:(3S,4S,5R)-6-(tert-butyldimethylsiloxy)-4-(4-methoxybenzyloxy)-5-methylhex-1-en-3-ol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3S,4S,5R)-6-(tert-butyldimethylsiloxy)-4-(4-methoxybenzyloxy)-5-methylhex-1-en-3-ol

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Technology Process of (3S,4S,5R)-6-(tert-butyldimethylsiloxy)-4-(4-methoxybenzyloxy)-5-methylhex-1-en-3-ol

There total 7 articles about (3S,4S,5R)-6-(tert-butyldimethylsiloxy)-4-(4-methoxybenzyloxy)-5-methylhex-1-en-3-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: 85.0%

: C₁₅H₂₂O₄

: 18162-48-6
tert-butyldimethylsilyl chloride

: 910215-33-7
(3S,4S,5R)-6-(tert-butyldimethylsiloxy)-4-(4-methoxybenzyloxy)-5-methylhex-1-en-3-ol

Guidance literature:: With 1H-imidazole; at 20 ℃; for 12h; stereoselective reaction; Cooling with ice;
DOI:10.1002/ejoc.201402830

Reference yield:

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 910215-33-7
(3S,4S,5R)-6-(tert-butyldimethylsiloxy)-4-(4-methoxybenzyloxy)-5-methylhex-1-en-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1: scandium tris(trifluoromethanesulfonate) / toluene / 0.5 h / 20 °C

2: lithium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 1 h / 0 °C

3: 1,2-bis(phenylsulfinyl)ethane palladium(II) acetate; (R,R)-N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminochromium(III) chloride; p-benzoquinone / 1,4-dioxane / 45 °C

4: diisobutylaluminium hydride / dichloromethane / 1 h / -78 - 0 °C

5: 1H-imidazole / 12 h / 20 °C / Cooling with ice

With 1H-imidazole; (R,R)-N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminochromium(III) chloride; 1,2-bis(phenylsulfinyl)ethane palladium(II) acetate; dihydrogen peroxide; diisobutylaluminium hydride; p-benzoquinone; lithium hydroxide; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; toluene;
DOI:10.1002/ejoc.201402830

Reference yield:

: C₁₅H₁₈O₄

: 910215-33-7
(3S,4S,5R)-6-(tert-butyldimethylsiloxy)-4-(4-methoxybenzyloxy)-5-methylhex-1-en-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1: diisobutylaluminium hydride / dichloromethane / 1 h / -78 - 0 °C

2: 1H-imidazole / 12 h / 20 °C / Cooling with ice

With 1H-imidazole; diisobutylaluminium hydride; In dichloromethane;
DOI:10.1002/ejoc.201402830