(1S,4S,6S)-4-Hydroxy-1-methyl-7-oxa-bicyclo[4.1.0]heptan-2-one

Base Information

• Chemical Name: (1S,4S,6S)-4-Hydroxy-1-methyl-7-oxa-bicyclo[4.1.0]heptan-2-one
• CAS No.: 326496-91-7
• Molecular Formula: C₇H₁₀O₃
• Molecular Weight: 142.155
• Mol file: 326496-91-7.mol

Synonyms:(1S,4S,6S)-4-Hydroxy-1-methyl-7-oxa-bicyclo[4.1.0]heptan-2-one

Chemical Property of (1S,4S,6S)-4-Hydroxy-1-methyl-7-oxa-bicyclo[4.1.0]heptan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4S,6S)-4-Hydroxy-1-methyl-7-oxa-bicyclo[4.1.0]heptan-2-one

There total 1 articles about (1S,4S,6S)-4-Hydroxy-1-methyl-7-oxa-bicyclo[4.1.0]heptan-2-one 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:

d(4)-methanol (811-98-3) + (1S,4S,6S)-4-(1-acetylhydroperoxy-1-methoxyethyl)-1-methyl-7-oxabicyclo[4.1.0]heptan-2-one (326496-90-6) → deuteromethanol (1455-13-6) + deuteroacetic acid (758-12-3) + CH3C(O(2)H3C)3 + (1S,4S,6S)-4-Hydroxy-1-methyl-7-oxa-bicyclo[4.1.0]heptan-2-one (326496-91-7)

Guidance literature:

Product distribution;

DOI:10.1021/jo0161577

Reference yield:

(1S,4S,6S)-4-Hydroxy-1-methyl-7-oxa-bicyclo[4.1.0]heptan-2-one (326496-91-7) → <3S-(1E,3α,5β)>-<3,5-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-methylenecyclohexylidene>acetic acid ethyl ester (81506-23-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: imidazole / acetonitrile / 4 h / 20 °C

2.1: 76.1 percent / LiH / tetrahydrofuran / 21.5 h

3.1: Pd₂(dba)3(CHCl₃); PPh₃; 1,3-bis(1,1,1,3,3,3-hexafluoro-2-hydroxypropyl)benzene / toluene / 16 h / 40 °C

3.2: 84 percent / imidazole / dimethylformamide / 16 h / 20 °C

With 1H-imidazole; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 1,3-bis-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-benzene; lithium hydride; triphenylphosphine; In tetrahydrofuran; toluene; acetonitrile; 2.1: Wittig-Horner reaction;

DOI:10.1021/jo0161577

Reference yield:

(1S,4S,6S)-4-Hydroxy-1-methyl-7-oxa-bicyclo[4.1.0]heptan-2-one (326496-91-7) → [(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide (81522-68-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: imidazole / acetonitrile / 4 h / 20 °C

2.1: 76.1 percent / LiH / tetrahydrofuran / 21.5 h

3.1: Pd₂(dba)3(CHCl₃); PPh₃; 1,3-bis(1,1,1,3,3,3-hexafluoro-2-hydroxypropyl)benzene / toluene / 16 h / 40 °C

3.2: 84 percent / imidazole / dimethylformamide / 16 h / 20 °C

4.1: 94.5 percent / DIBALH / hexane / 0.5 h / -70 °C

5.1: 77.2 percent / 9-fluorenone-4-carboxylic acid / various solvent(s) / 6 h / Irradiation

6.1: triphosgene; Et₃N / hexane / 1.33 h / 5 - 20 °C

7.1: 22.3 g / NaH / dimethylformamide / -45 - 0 °C

With 1H-imidazole; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; bis(trichloromethyl) carbonate; 1,3-bis-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-benzene; 9-oxo-9H-fluorene-4-carboxylic acid; lithium hydride; sodium hydride; diisobutylaluminium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; toluene; acetonitrile; 2.1: Wittig-Horner reaction;

DOI:10.1021/jo0161577

upstream raw materials:

d⁽⁴⁾-methanol

(1S,4S,6S)-4-(1-acetylhydroperoxy-1-methoxyethyl)-1-methyl-7-oxabicyclo[4.1.0]heptan-2-one

Downstream raw materials:

[3S-(1Z,3α,5β)]-2-[3,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methylenecyclohexylidene]ethanol

[(3S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2-methylene-cyclohex-(E)-ylidene]-acetic acid ethyl ester

<3S-(1E,3α,5β)>-<3,5-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-methylenecyclohexylidene>acetic acid ethyl ester

[(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide