(4S,5S)-4,5-dihydroxy-2-methylcyclohex-2-enone

Base Information

Chemical Name:(4S,5S)-4,5-dihydroxy-2-methylcyclohex-2-enone
CAS No.:1111764-90-9
Molecular Formula:C₇H₁₀O₃
Molecular Weight:142.155
Hs Code.:

Synonyms:(4S,5S)-4,5-dihydroxy-2-methylcyclohex-2-enone

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Chemical Property of (4S,5S)-4,5-dihydroxy-2-methylcyclohex-2-enone

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Technology Process of (4S,5S)-4,5-dihydroxy-2-methylcyclohex-2-enone

There total 10 articles about (4S,5S)-4,5-dihydroxy-2-methylcyclohex-2-enone 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: 84.0%

: 1401424-17-6
(2R,3R,4aS,8aS)-2,3-dimethoxy-2,3,7-trimethyl-2,3,4a,5-tetrahydrobenzo[b][1,4]dioxin-6(8aH)-one

: 1111764-90-9
(4S,5S)-4,5-dihydroxy-2-methylcyclohex-2-enone

Guidance literature:: With trifluoroacetic acid; In water; at 20 ℃; for 0.25h; Inert atmosphere;
DOI:10.1039/c2ob26406d

Reference yield:

: 299437-54-0
(2R,3R,4aS,6S,8aS)-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,6,8ahexahydrobenzo[b][1,4]dioxin-6-ol

: 1111764-90-9
(4S,5S)-4,5-dihydroxy-2-methylcyclohex-2-enone

Guidance literature:: Multi-step reaction with 4 steps

1: manganese(IV) oxide / dichloromethane / 12 h / 20 °C / Inert atmosphere

2: iodine; dmap; pyridine / tetrachloromethane / 2 h / 20 °C / Inert atmosphere

3: trans-bromo(N-succinimidyl)-bis(triphenylphosphine)palladium(II) / tetrahydrofuran / 24 h / 100 °C / Inert atmosphere; Sealed tube

4: trifluoroacetic acid / water / 0.25 h / 20 °C / Inert atmosphere

With pyridine; dmap; manganese(IV) oxide; trans-bromo(N-succinimidyl)-bis(triphenylphosphine)palladium(II); iodine; trifluoroacetic acid; In tetrahydrofuran; tetrachloromethane; dichloromethane; water; 3: |Stille Cross Coupling;
DOI:10.1039/c2ob26406d

Reference yield:

: 1165952-92-0
cyclohexa-1,4-diene

: 1111764-90-9
(4S,5S)-4,5-dihydroxy-2-methylcyclohex-2-enone

Guidance literature:: Multi-step reaction with 10 steps

1.1: 3-chloro-benzenecarboperoxoic acid; sodium hydrogencarbonate / dichloromethane; water / 23.75 h / 0 - 20 °C / Inert atmosphere

2.1: (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicydene)-1,2-cyclohexanediaminocobalt(II); oxygen / tert-butyl methyl ether / 1 h

2.2: 94 h / 20 °C

3.1: Amberlyst A₂₆ (OH form) / methanol; tetrahydrofuran / 5 h / 20 °C

4.1: boron trifluoride diethyl etherate / methanol / 16 h / 20 °C / Inert atmosphere

5.1: 3-chloro-benzenecarboperoxoic acid; sodium hydrogencarbonate / dichloromethane / 17 h / 0 - 20 °C / Inert atmosphere

6.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 19 h / 0 - 20 °C / Inert atmosphere

7.1: manganese(IV) oxide / dichloromethane / 12 h / 20 °C / Inert atmosphere

8.1: iodine; dmap; pyridine / tetrachloromethane / 2 h / 20 °C / Inert atmosphere

9.1: trans-bromo(N-succinimidyl)-bis(triphenylphosphine)palladium(II) / tetrahydrofuran / 24 h / 100 °C / Inert atmosphere; Sealed tube

10.1: trifluoroacetic acid / water / 0.25 h / 20 °C / Inert atmosphere

With pyridine; dmap; manganese(IV) oxide; (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicydene)-1,2-cyclohexanediaminocobalt(II); trans-bromo(N-succinimidyl)-bis(triphenylphosphine)palladium(II); boron trifluoride diethyl etherate; iodine; oxygen; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; tetrachloromethane; hexane; dichloromethane; tert-butyl methyl ether; water; 9.1: |Stille Cross Coupling;
DOI:10.1039/c2ob26406d