1-[(2R,3aS,6R,7S,7aR)-6,7-dihydroxy-6-methyl-3-methylideneoctahydro-1-benzofuran-2-yl]-3-methylbutan-1-one

Base Information

• Chemical Name: 1-[(2R,3aS,6R,7S,7aR)-6,7-dihydroxy-6-methyl-3-methylideneoctahydro-1-benzofuran-2-yl]-3-methylbutan-1-one
• CAS No.: 160299-94-5
• Molecular Formula: C₁₅H₂₄O₄
• Molecular Weight: 268.353
• Mol file: 160299-94-5.mol

Synonyms:1-Butanone,3-methyl-1-(octahydro-6,7-dihydroxy-6-methyl-3-methylene-2-benzofuranyl)-, (2a,3aa,6a,7a,7aa)-(+)-; Cheimonophyllon E

Chemical Property of 1-[(2R,3aS,6R,7S,7aR)-6,7-dihydroxy-6-methyl-3-methylideneoctahydro-1-benzofuran-2-yl]-3-methylbutan-1-one

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 399.514°C at 760 mmHg
• Flash Point: 142.865°C
• Density: 1.141g/cm³

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(2R,3aS,6R,7S,7aR)-6,7-dihydroxy-6-methyl-3-methylideneoctahydro-1-benzofuran-2-yl]-3-methylbutan-1-one

There total 54 articles about 1-[(2R,3aS,6R,7S,7aR)-6,7-dihydroxy-6-methyl-3-methylideneoctahydro-1-benzofuran-2-yl]-3-methylbutan-1-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: 78.0%

3-Methyl-1-((3aR,5aS,7R,8aR,8bS)-2,2,3a-trimethyl-6-methylene-octahydro-furo[2',3':3,4]benzo[1,2-d][1,3]dioxol-7-yl)-butan-1-one (851051-13-3) → (-)-cheimonophyllon E (160299-94-5)

Guidance literature:

With pyridinium p-toluenesulfonate; In methanol; at 50 ℃; for 48h;

DOI:10.1016/j.tetlet.2005.02.058

Reference yield: 48.0%

3-Methyl-1-((2S,3aR,7aR)-6-methyl-3-methylene-2,3,3a,4,5,7a-hexahydro-benzofuran-2-yl)-butan-1-one → 1-((2S,3S,3aS,7aR)-3-Hydroxy-3-hydroxymethyl-6-methyl-2,3,3a,4,5,7a-hexahydro-benzofuran-2-yl)-3-methyl-butan-1-one + (+/-)-cheimonophyllon E (160299-94-5)

Guidance literature:

With N-methyl-2-indolinone; osmium(VIII) oxide; In water; acetone; tert-butyl alcohol; at 0 ℃;

DOI:10.1016/S0040-4039(01)00817-6

Reference yield: 42.0%

(1R,6R,8S)-3-methyl-8-(3-methylbutanoyl)-7-methylene-9-oxabicyclo[4.3.0]non-2-ene (359887-14-2) → (1R,6S,7S,8S)-7-hydroxymethyl-3-methyl-8-(3-methylbutanoyl)-9-oxabicyclo[4.3.0]non-2-en-7-ol + (+)-cheimonophyllon E (160299-94-5)

Guidance literature:

With osmium(VIII) oxide; N-methyl-2-indolinone; In water; acetone; tert-butyl alcohol; at 0 ℃; for 2.5h;

DOI:10.1021/jo0203140

upstream raw materials:

Lepistirone

3-Methyl-1-((3aR,5aS,7R,8aR,8bS)-2,2,3a-trimethyl-6-methylene-octahydro-furo[2',3':3,4]benzo[1,2-d][1,3]dioxol-7-yl)-butan-1-one

(1S,2R,5S,6S)-5-(1-Chloromethyl-vinyl)-2-methyl-7-oxa-bicyclo[4.1.0]heptan-2-ol

(3aS,6R,7S,7aR)-6-Methyl-3-methylene-octahydro-benzofuran-6,7-diol