2-[[(1S,4aα)-Decahydro-5,5,8aβ-trimethyl-2-methylenenaphthalen-1β-yl]methyl]-3-methylfuran

Base Information

• Chemical Name: 2-[[(1S,4aα)-Decahydro-5,5,8aβ-trimethyl-2-methylenenaphthalen-1β-yl]methyl]-3-methylfuran
• CAS No.: 67779-53-7
• Molecular Formula: C20H30O
• Molecular Weight: 286.45
• Mol file: 67779-53-7.mol

Synonyms:3-Methyl-2-((1S,8aS)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-ylmethyl)-furan;

Chemical Property of 2-[[(1S,4aα)-Decahydro-5,5,8aβ-trimethyl-2-methylenenaphthalen-1β-yl]methyl]-3-methylfuran

Chemical Property:

• PSA: 13.14000
• LogP: 5.92930

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-[[(1S,4aα)-Decahydro-5,5,8aβ-trimethyl-2-methylenenaphthalen-1β-yl]methyl]-3-methylfuran

There total 11 articles about 2-[[(1S,4aα)-Decahydro-5,5,8aβ-trimethyl-2-methylenenaphthalen-1β-yl]methyl]-3-methylfuran 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: 65.0%

16-chloro-12,15-epoxylabda-8(17),12,14-triene (130468-25-6) → (-)-pumiloxide (67779-53-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 0.5h; Ambient temperature;

Reference yield:

(12Z)-labda-8(17),12,14-triene (17990-20-4) → pumiloxide (67779-53-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) oxygen, rose bengal, 2.) triethyl phosphite / 1.) CH₂Cl₂, CH₃OH, irradiation, 45 min

2: 3 mg / Fe₂SO₄*7H₂O / tetrahydrofuran; H₂O / 1 h

With Fe₂SO₄*7H₂O; oxygen; rose bengal; triethyl phosphite; In tetrahydrofuran; water;

DOI:10.1021/jo00320a027

Reference yield:

trans-biformene (10395-42-3) → pumiloxide (67779-53-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) oxygen, rose bengal, 2.) triethyl phosphite / 1.) CH₂Cl₂, CH₃OH, irradiation, 75 min

2: 3 mg / Fe₂SO₄*7H₂O / tetrahydrofuran; H₂O / 1 h

With Fe₂SO₄*7H₂O; oxygen; rose bengal; triethyl phosphite; In tetrahydrofuran; water;

DOI:10.1021/jo00320a027

upstream raw materials:

16-chloro-12,15-epoxylabda-8⁽¹⁷⁾,12,14-triene

sclareol oxide

8α,13β-epoxy-15-norlabdan-14-oic acid

(1R,2R,8aS)-2,5,5,8a-tetramethyl-1-(2-oxoethyl)decahydronaphthalen-2-yl acetate

Refernces

• 1、 Cambie, Richard C.,Moratti, Stephen C.,Rutledge, Peter S.,Weston, Roderick J.,Woodgate, Paul D.. "A Synthesis of (-)-12,15-Epoxylabda-8(17),12,14-trien-16-yl Acetate and (-)-Pumiloxide". . p. 1151 - 1162. Retrieved 2007/10/02.