[(4E)-(1R,3R,5R)-3-[(tert-butyldimethylsilyl)oxy]-1,5-dihydroxy-4-[3-(methoxymethoxy)propylidene]cyclohexyl]methanol

Base Information

Chemical Name:[(4E)-(1R,3R,5R)-3-[(tert-butyldimethylsilyl)oxy]-1,5-dihydroxy-4-[3-(methoxymethoxy)propylidene]cyclohexyl]methanol
CAS No.:766529-96-8
Molecular Formula:C₁₈H₃₆O₆Si
Molecular Weight:376.566
Hs Code.:

Synonyms:[(4E)-(1R,3R,5R)-3-[(tert-butyldimethylsilyl)oxy]-1,5-dihydroxy-4-[3-(methoxymethoxy)propylidene]cyclohexyl]methanol

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Chemical Property of [(4E)-(1R,3R,5R)-3-[(tert-butyldimethylsilyl)oxy]-1,5-dihydroxy-4-[3-(methoxymethoxy)propylidene]cyclohexyl]methanol

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Technology Process of [(4E)-(1R,3R,5R)-3-[(tert-butyldimethylsilyl)oxy]-1,5-dihydroxy-4-[3-(methoxymethoxy)propylidene]cyclohexyl]methanol

There total 7 articles about [(4E)-(1R,3R,5R)-3-[(tert-butyldimethylsilyl)oxy]-1,5-dihydroxy-4-[3-(methoxymethoxy)propylidene]cyclohexyl]methanol 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: 79.0%

: 766529-89-9
(4E)-(1R,3R,5R)-1-acetoxy-3-[(tert-butyldimethylsilyl)oxy]-6-oxa-4-[3'-(methoxymethoxy)propylidene]bicyclo[3.2.1]octan-7-one

: 766529-96-8
[(4E)-(1R,3R,5R)-3-[(tert-butyldimethylsilyl)oxy]-1,5-dihydroxy-4-[3-(methoxymethoxy)propylidene]cyclohexyl]methanol

Guidance literature:: With sodium tetrahydroborate; In ethanol; at 0 - 20 ℃; for 13h;
DOI:10.1021/jm051082a

Reference yield:

: 78365-43-2
1-bromo-3-(methoxymethoxy)propane

: 766529-96-8
[(4E)-(1R,3R,5R)-3-[(tert-butyldimethylsilyl)oxy]-1,5-dihydroxy-4-[3-(methoxymethoxy)propylidene]cyclohexyl]methanol

Guidance literature:: Multi-step reaction with 3 steps

1.1: toluene / 20 h / 100 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 - 20 °C

2.2: tetrahydrofuran; hexane / 3 h / -78 °C

3.1: 79 percent / NaBH₄ / ethanol / 13 h / 0 - 20 °C

With sodium tetrahydroborate; n-butyllithium; In tetrahydrofuran; ethanol; hexane; toluene; 2.2: Wittig reaction;
DOI:10.1021/jm051082a

Reference yield:

: 665-27-0
1,5-quinide

: 766529-96-8
[(4E)-(1R,3R,5R)-3-[(tert-butyldimethylsilyl)oxy]-1,5-dihydroxy-4-[3-(methoxymethoxy)propylidene]cyclohexyl]methanol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 76 percent / imidazole / dimethylformamide / 1.5 h / 0 - 20 °C

2.1: Dess-Martin periodinate / CH₂Cl₂ / 18 h / 20 °C

3.1: 1.51 g / pyridine / 3 h / 20 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 - 20 °C

4.2: tetrahydrofuran; hexane / 3 h / -78 °C

5.1: 79 percent / NaBH₄ / ethanol / 13 h / 0 - 20 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; n-butyllithium; Dess-Martin periodane; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; 4.2: Wittig reaction;
DOI:10.1021/jm051082a