(1S,2S,3S,6R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-6-hydroxycyclohex-4-ene-1,2,3-triyl triacetate

Base Information

Chemical Name:(1S,2S,3S,6R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-6-hydroxycyclohex-4-ene-1,2,3-triyl triacetate
CAS No.:853234-39-6
Molecular Formula:C₁₉H₃₂O₈Si
Molecular Weight:416.544
Hs Code.:

Synonyms:(1S,2S,3S,6R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-6-hydroxycyclohex-4-ene-1,2,3-triyl triacetate

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Chemical Property of (1S,2S,3S,6R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-6-hydroxycyclohex-4-ene-1,2,3-triyl triacetate

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Technology Process of (1S,2S,3S,6R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-6-hydroxycyclohex-4-ene-1,2,3-triyl triacetate

There total 5 articles about (1S,2S,3S,6R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-6-hydroxycyclohex-4-ene-1,2,3-triyl triacetate 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: 80.0%

: 853234-38-5
Acetic acid (1R,5S,6S)-5,6-diacetoxy-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-cyclohex-3-enyl ester

: 853234-39-6
(1S,2S,3S,6R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-6-hydroxycyclohex-4-ene-1,2,3-triyl triacetate

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride; In methanol; at 0 ℃;
DOI:10.1016/j.tetlet.2005.03.087

Reference yield:

: 853234-36-3
Acetic acid (1S,4R,4aS,5S,6R,7R,8aR)-8a-(tert-butyl-dimethyl-silanyloxymethyl)-6,7-dihydroxy-8-oxo-1,4,4a,5,6,7,8,8a-octahydro-1,4-methano-naphthalen-5-yl ester

: 853234-39-6
(1S,2S,3S,6R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-6-hydroxycyclohex-4-ene-1,2,3-triyl triacetate

Guidance literature:: Multi-step reaction with 3 steps

1: 100 percent / pyridine / CH₂Cl₂ / 2 h

2: 91 percent / Ph₂O / 0.25 h / 230 °C

3: 80 percent / NaBH₄; CeCl₃*7H₂O / methanol / 0 °C

With pyridine; sodium tetrahydroborate; cerium(III) chloride; diphenylether; In methanol; dichloromethane; 2: retro-Diels-Alder reaction;
DOI:10.1016/j.tetlet.2005.03.087

Reference yield:

: 853234-37-4
Acetic acid (1S,4R,4aS,5S,6S,7R,8aR)-6,7-diacetoxy-8a-(tert-butyl-dimethyl-silanyloxymethyl)-8-oxo-1,4,4a,5,6,7,8,8a-octahydro-1,4-methano-naphthalen-5-yl ester

: 853234-39-6
(1S,2S,3S,6R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-6-hydroxycyclohex-4-ene-1,2,3-triyl triacetate

Guidance literature:: Multi-step reaction with 2 steps

1: 91 percent / Ph₂O / 0.25 h / 230 °C

2: 80 percent / NaBH₄; CeCl₃*7H₂O / methanol / 0 °C

With sodium tetrahydroborate; cerium(III) chloride; diphenylether; In methanol; 1: retro-Diels-Alder reaction;
DOI:10.1016/j.tetlet.2005.03.087