(3S,4S,5S,6R)-6-Chloro-3-hydroxy-4,5-bis-trimethylsilanyloxy-cyclohex-1-enecarboxylic acid methyl ester

Base Information

Chemical Name:(3S,4S,5S,6R)-6-Chloro-3-hydroxy-4,5-bis-trimethylsilanyloxy-cyclohex-1-enecarboxylic acid methyl ester
CAS No.:863983-66-8
Molecular Formula:C₁₄H₂₇ClO₅Si₂
Molecular Weight:366.989
Hs Code.:

Synonyms:(3S,4S,5S,6R)-6-Chloro-3-hydroxy-4,5-bis-trimethylsilanyloxy-cyclohex-1-enecarboxylic acid methyl ester

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Chemical Property of (3S,4S,5S,6R)-6-Chloro-3-hydroxy-4,5-bis-trimethylsilanyloxy-cyclohex-1-enecarboxylic acid methyl ester

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Technology Process of (3S,4S,5S,6R)-6-Chloro-3-hydroxy-4,5-bis-trimethylsilanyloxy-cyclohex-1-enecarboxylic acid methyl ester

There total 12 articles about (3S,4S,5S,6R)-6-Chloro-3-hydroxy-4,5-bis-trimethylsilanyloxy-cyclohex-1-enecarboxylic acid methyl ester 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: 100.0%

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

: 863983-66-8
(3S,4S,5S,6R)-6-Chloro-3-hydroxy-4,5-bis-trimethylsilanyloxy-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: With sodium tetrahydroborate; In methanol; at -10 ℃; for 0.5h;
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

: 863983-66-8
(3S,4S,5S,6R)-6-Chloro-3-hydroxy-4,5-bis-trimethylsilanyloxy-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 11 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

11: NaBH₄ / methanol / -10 °C

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

Reference yield:

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

: 863983-66-8
(3S,4S,5S,6R)-6-Chloro-3-hydroxy-4,5-bis-trimethylsilanyloxy-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 7 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

6: 65 percent / Martin's sulfrane / CH₂Cl₂

7: NaBH₄ / methanol / -10 °C

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