methyl (1S,4R,5S,6S)-6-chloro-1-hydroxy-4,5-bis(trimethylsiloxy)-3-oxocyclohexanecarboxylate

Base Information

Chemical Name:methyl (1S,4R,5S,6S)-6-chloro-1-hydroxy-4,5-bis(trimethylsiloxy)-3-oxocyclohexanecarboxylate
CAS No.:863983-62-4
Molecular Formula:C₁₄H₂₇ClO₆Si₂
Molecular Weight:382.989
Hs Code.:

Synonyms:methyl (1S,4R,5S,6S)-6-chloro-1-hydroxy-4,5-bis(trimethylsiloxy)-3-oxocyclohexanecarboxylate

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Chemical Property of methyl (1S,4R,5S,6S)-6-chloro-1-hydroxy-4,5-bis(trimethylsiloxy)-3-oxocyclohexanecarboxylate

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Technology Process of methyl (1S,4R,5S,6S)-6-chloro-1-hydroxy-4,5-bis(trimethylsiloxy)-3-oxocyclohexanecarboxylate

There total 10 articles about methyl (1S,4R,5S,6S)-6-chloro-1-hydroxy-4,5-bis(trimethylsiloxy)-3-oxocyclohexanecarboxylate 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: 71.0%

: 863983-61-3
methyl (1S,4R,5S,6S)-6-chloro-1,4,5-trihydroxy-3-oxocyclohexanecarboxylate

: 18162-48-6
tert-butyldimethylsilyl chloride

: 863983-62-4
methyl (1S,4R,5S,6S)-6-chloro-1-hydroxy-4,5-bis(trimethylsiloxy)-3-oxocyclohexanecarboxylate

Guidance literature:: With triethylamine;
DOI:10.1246/cl.2005.1062

Reference yield:

: 868526-03-8
(1R,4S,5R)-1,4-Dihydroxy-6-oxa-bicyclo[3.2.1]octane-3,7-dione

: 863983-62-4
methyl (1S,4R,5S,6S)-6-chloro-1-hydroxy-4,5-bis(trimethylsiloxy)-3-oxocyclohexanecarboxylate

Guidance literature:: Multi-step reaction with 9 steps

1: toluene / Heating

2: N-chlorosuccinimide / dimethylformamide / 20 °C

3: 68 percent / NaBH₄

4: 67 percent / n-Bu₄NF

5: 30 percent / TsOH / CH₂Cl₂

6: 90 percent / methanol

7: 78 percent / Dess-Martin periodinane / CH₂Cl₂

8: 70 percent / trifluoroacetic acid / methanol

9: 71 percent / Et₃N

With sodium tetrahydroborate; N-chloro-succinimide; tetrabutyl ammonium fluoride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1246/cl.2005.1062

Reference yield:

: 863983-57-7
(1S,3R,4R,5S,6S)-6-chloro-1,4,5-trihydroxycyclohexane-1,3-carbolactone

: 863983-62-4
methyl (1S,4R,5S,6S)-6-chloro-1-hydroxy-4,5-bis(trimethylsiloxy)-3-oxocyclohexanecarboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 30 percent / TsOH / CH₂Cl₂

2: 90 percent / methanol

3: 78 percent / Dess-Martin periodinane / CH₂Cl₂

4: 70 percent / trifluoroacetic acid / methanol

5: 71 percent / Et₃N

With Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; In methanol; dichloromethane;
DOI:10.1246/cl.2005.1062