(R)-4-((1S,2R,3S,5R)-3-Hydroxy-2-methyl-6-oxa-bicyclo[3.1.0]hex-2-yl)-4-methyl-cyclohex-2-enone

Base Information

Chemical Name:(R)-4-((1S,2R,3S,5R)-3-Hydroxy-2-methyl-6-oxa-bicyclo[3.1.0]hex-2-yl)-4-methyl-cyclohex-2-enone
CAS No.:74501-16-9
Molecular Formula:C₁₃H₁₈O₃
Molecular Weight:222.284
Hs Code.:

Synonyms:(R)-4-((1S,2R,3S,5R)-3-Hydroxy-2-methyl-6-oxa-bicyclo[3.1.0]hex-2-yl)-4-methyl-cyclohex-2-enone

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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 (R)-4-((1S,2R,3S,5R)-3-Hydroxy-2-methyl-6-oxa-bicyclo[3.1.0]hex-2-yl)-4-methyl-cyclohex-2-enone

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Technology Process of (R)-4-((1S,2R,3S,5R)-3-Hydroxy-2-methyl-6-oxa-bicyclo[3.1.0]hex-2-yl)-4-methyl-cyclohex-2-enone

There total 7 articles about (R)-4-((1S,2R,3S,5R)-3-Hydroxy-2-methyl-6-oxa-bicyclo[3.1.0]hex-2-yl)-4-methyl-cyclohex-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:

: 74501-09-0
tert-butyldimethyl((4-methylcyclohexa-1,3-dien-1-yl)oxy)silane

: 74501-16-9
(R)-4-((1S,2R,3S,5R)-3-Hydroxy-2-methyl-6-oxa-bicyclo[3.1.0]hex-2-yl)-4-methyl-cyclohex-2-enone

Guidance literature:: Multi-step reaction with 7 steps

1: 90 percent / benzene / 120 h / 25 °C

2: 1.) t-BuOOH, Triton B, 2.) NaOH / 1.) THF, -20 deg C, 2.) 25 deg C

3: 1.) t-BuOOH, Triton B, 2.) Li, NH₃ / 1.) THF, 25 deg C, 2.) THF, EtOH

4: 1.) Ac₂O, C₅H₅N, 2.) HMPA / 1.) 0 deg C, 2.) H₂O, irradiation

6: 80 percent / sodium hydride / tetrahydrofuran / 0 °C

7: 1.) t-BuOOH, VO(acac)2, 2.) K₂CO₃ / 1.) CH₂Cl₂, 2.) MeOH

With pyridine; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; bis(acetylacetonate)oxovanadium; ammonia; acetic anhydride; N-benzyl-trimethylammonium hydroxide; lithium; sodium hydride; potassium carbonate; In tetrahydrofuran; benzene;
DOI:10.1021/ja00530a072

Reference yield:

: 74501-13-6
(1S,3R,3aS,4S,7S,7aS)-7-(tert-Butyl-dimethyl-silanyloxy)-3a,4-dimethyl-2,3,3a,4,7,7a-hexahydro-1H-4,7-ethano-indene-1,3-diol

: 74501-16-9
(R)-4-((1S,2R,3S,5R)-3-Hydroxy-2-methyl-6-oxa-bicyclo[3.1.0]hex-2-yl)-4-methyl-cyclohex-2-enone

Guidance literature:: Multi-step reaction with 3 steps

2: 80 percent / sodium hydride / tetrahydrofuran / 0 °C

3: 1.) t-BuOOH, VO(acac)2, 2.) K₂CO₃ / 1.) CH₂Cl₂, 2.) MeOH

With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; sodium hydride; potassium carbonate; In tetrahydrofuran;
DOI:10.1021/ja00530a072

Reference yield:

: 74501-12-5
(1S,3R,3aS,4S,7S,7aS)-7-(tert-Butyl-dimethyl-silanyloxy)-3a-hydroxymethyl-4-methyl-2,3,3a,4,7,7a-hexahydro-1H-4,7-ethano-indene-1,3-diol

: 74501-16-9
(R)-4-((1S,2R,3S,5R)-3-Hydroxy-2-methyl-6-oxa-bicyclo[3.1.0]hex-2-yl)-4-methyl-cyclohex-2-enone

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) Ac₂O, C₅H₅N, 2.) HMPA / 1.) 0 deg C, 2.) H₂O, irradiation

3: 80 percent / sodium hydride / tetrahydrofuran / 0 °C

4: 1.) t-BuOOH, VO(acac)2, 2.) K₂CO₃ / 1.) CH₂Cl₂, 2.) MeOH

With pyridine; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; bis(acetylacetonate)oxovanadium; acetic anhydride; sodium hydride; potassium carbonate; In tetrahydrofuran;
DOI:10.1021/ja00530a072