1-{(5S,6R)-6-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-ethanone

Base Information

Chemical Name:1-{(5S,6R)-6-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-ethanone
CAS No.:82294-14-2
Molecular Formula:C₂₈H₄₀O₄Si
Molecular Weight:468.709
Hs Code.:

Synonyms:1-{(5S,6R)-6-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-ethanone

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Chemical Property of 1-{(5S,6R)-6-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-ethanone

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Technology Process of 1-{(5S,6R)-6-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-ethanone

There total 39 articles about 1-{(5S,6R)-6-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-ethanone 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: 97.0%

: 803699-27-6
(S)-1-{(4R,5S,6R)-6-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-ethanol

: 82294-14-2
(2R,3S,4S,5R)-1-tert-butyldiphenylsilyloxy-2,4-dimethyl-3,5-isopropylidenedioxyheptan-6-one

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 0 ℃;
DOI:10.1055/s-2004-831332

Reference yield: 86.0%

: 124871-59-6
(2R,3S,4S,5R)-1-tert-butyldiphenylsilyloxy-2,4-dimethyl-6-hydroxy-3,5-isopropylidenedioxyheptane

: 82294-14-2
(2R,3S,4S,5R)-1-tert-butyldiphenylsilyloxy-2,4-dimethyl-3,5-isopropylidenedioxyheptan-6-one

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -60 - -55 ℃; for 1h;
DOI:10.1248/cpb.37.1167

Reference yield:

: 39947-42-7
(1S,2S)-(+)-1-hydroxy-2-methyl-3-cyclopentene

: 82294-14-2
1-{(5S,6R)-6-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-ethanone

Guidance literature:: Multi-step reaction with 11 steps

1: 86 percent / tert-butyl hydroperoxide / VO(acac)2 / benzene

2: Jones oxidation / 0.42 h / 0 °C

3: 1.) Et₃N, 2.) DMAP / 1.) CH₂Cl₂, 0.5 H

4: 2.) Et₃N / 1.) ether, -78 deg C

5: 1.) ozone, 2.) NaBH₄, 3.) 2N HCl

6: Dibal / tetrahydrofuran / -78 °C

7: diethyl ether

8: tetrabutylammonium fluoride / tetrahydrofuran

9: DMAP / CH₂Cl₂; triethylamine

10: pyridinium tosylate

11: ozone

With hydrogenchloride; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; ozone; triethylamine; bis(acetylacetonate)oxovanadium; In tetrahydrofuran; diethyl ether; dichloromethane; triethylamine; benzene;
DOI:10.1021/ja00381a035