methyl (4R,5S,6R)-6-chloro-4,5-bis(trimethylsiloxy)-3-oxocyclohex-1-enecarboxylate

Base Information

Chemical Name:methyl (4R,5S,6R)-6-chloro-4,5-bis(trimethylsiloxy)-3-oxocyclohex-1-enecarboxylate
CAS No.:863983-63-5
Molecular Formula:C₁₄H₂₅ClO₅Si₂
Molecular Weight:364.974
Hs Code.:

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

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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 methyl (4R,5S,6R)-6-chloro-4,5-bis(trimethylsiloxy)-3-oxocyclohex-1-enecarboxylate

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

There total 12 articles about methyl (4R,5S,6R)-6-chloro-4,5-bis(trimethylsiloxy)-3-oxocyclohex-1-enecarboxylate 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: 65.0%

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

: 863983-63-5
methyl (4R,5S,6R)-6-chloro-4,5-bis(trimethylsiloxy)-3-oxocyclohex-1-enecarboxylate

Guidance literature:: With Martins sulfurane; In dichloromethane;
DOI:10.1246/cl.2005.1062

Reference yield: 30.0%

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

: 863983-64-6
methyl (4R,5S,6R)-6-chloro-4,5-dihydroxy-3-oxocyclohex-1-enecarboxylate

: 863983-63-5
methyl (4R,5S,6R)-6-chloro-4,5-bis(trimethylsiloxy)-3-oxocyclohex-1-enecarboxylate

Guidance literature:: With thionyl chloride; trimethylamine; In dichloromethane; at 0 ℃; for 3h;
DOI:10.1055/s-2007-990798

Reference yield:

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

: 863983-63-5
methyl (4R,5S,6R)-6-chloro-4,5-bis(trimethylsiloxy)-3-oxocyclohex-1-enecarboxylate

Guidance literature:: Multi-step reaction with 10 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

10: 65 percent / Martin's sulfrane / CH₂Cl₂

With sodium tetrahydroborate; N-chloro-succinimide; Martins sulfurane; 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