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

Base Information

Chemical Name:methyl (1S,4R,5S,6S)-6-chloro-1,4,5-trihydroxy-3-oxocyclohexanecarboxylate
CAS No.:863983-61-3
Molecular Formula:C₈H₁₁ClO₆
Molecular Weight:238.625
Hs Code.:

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

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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 (1S,4R,5S,6S)-6-chloro-1,4,5-trihydroxy-3-oxocyclohexanecarboxylate

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

There total 9 articles about methyl (1S,4R,5S,6S)-6-chloro-1,4,5-trihydroxy-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: 70.0%

: 863983-60-2
methyl (1S,4R,5S,6S)-6-chloro-1-hydroxy-4,5-(isopropylidenedioxy)-3-oxocyclohexanecarboxylate

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

Guidance literature:: With trifluoroacetic acid; In methanol;
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

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

Guidance literature:: Multi-step reaction with 8 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

With sodium tetrahydroborate; N-chloro-succinimide; tetrabutyl ammonium fluoride; Dess-Martin periodane; toluene-4-sulfonic acid; 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

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

Guidance literature:: Multi-step reaction with 4 steps

1: 30 percent / TsOH / CH₂Cl₂

2: 90 percent / methanol

3: 78 percent / Dess-Martin periodinane / CH₂Cl₂

4: 70 percent / trifluoroacetic acid / methanol

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