(4aR,6S,8aS)-3,4,4a,5,6,7,8,8a-octahydro-6-benzyloxy-1-<2-(3-furyl)-2-p-tosylethyl>-2,5,5,8a-tetramethylnaphthalene

Base Information

• Chemical Name: (4aR,6S,8aS)-3,4,4a,5,6,7,8,8a-octahydro-6-benzyloxy-1-<2-(3-furyl)-2-p-tosylethyl>-2,5,5,8a-tetramethylnaphthalene
• CAS No.: 115626-95-4
• Molecular Formula: C₃₄H₄₂O₄S
• Molecular Weight: 546.771
• Mol file: 115626-95-4.mol

Synonyms:

Chemical Property of (4aR,6S,8aS)-3,4,4a,5,6,7,8,8a-octahydro-6-benzyloxy-1-<2-(3-furyl)-2-p-tosylethyl>-2,5,5,8a-tetramethylnaphthalene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aR,6S,8aS)-3,4,4a,5,6,7,8,8a-octahydro-6-benzyloxy-1-<2-(3-furyl)-2-p-tosylethyl>-2,5,5,8a-tetramethylnaphthalene

There total 5 articles about (4aR,6S,8aS)-3,4,4a,5,6,7,8,8a-octahydro-6-benzyloxy-1-<2-(3-furyl)-2-p-tosylethyl>-2,5,5,8a-tetramethylnaphthalene 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:

methyl (1S,4aR,6S,8aS)-(+)-1,4,4a,5,6,7,8,8a-octahydro-6-hydroxy-2,5,5,8a-tetramethyl-1-naphthalenecarboxylate (10247-03-7) → (4aR,6S,8aS)-3,4,4a,5,6,7,8,8a-octahydro-6-benzyloxy-1-<2-(3-furyl)-2-p-tosylethyl>-2,5,5,8a-tetramethylnaphthalene (115626-95-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaH / 1.) DMF, rt then 40 deg C 1 h; 2.) DMF, 40 deg C 2 h

2: 59 percent / LAH / diethyl ether / 4 h / Ambient temperature

3: 1.) MsCl, Et₃N; 2.) LiBr / 1.) CH₂Cl₂, -60 deg C, 30 min; 2.) CH₂Cl₂-THF, -60 deg C then -20 deg C 45 min

4: 1.) n-BuLi / 1.) THF-HMPA-hexane, -78 deg C, 20 min; 2.) THF-HMPA-hexane, -78 deg C, 1.5 h

With lithium aluminium tetrahydride; n-butyllithium; sodium hydride; methanesulfonyl chloride; triethylamine; lithium bromide; In diethyl ether;

DOI:10.1016/S0040-4020(01)81631-8

Reference yield:

benzyl chloride (100-44-7) → (4aR,6S,8aS)-3,4,4a,5,6,7,8,8a-octahydro-6-benzyloxy-1-<2-(3-furyl)-2-p-tosylethyl>-2,5,5,8a-tetramethylnaphthalene (115626-95-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaH / 1.) DMF, rt then 40 deg C 1 h; 2.) DMF, 40 deg C 2 h

2: 59 percent / LAH / diethyl ether / 4 h / Ambient temperature

3: 1.) MsCl, Et₃N; 2.) LiBr / 1.) CH₂Cl₂, -60 deg C, 30 min; 2.) CH₂Cl₂-THF, -60 deg C then -20 deg C 45 min

4: 1.) n-BuLi / 1.) THF-HMPA-hexane, -78 deg C, 20 min; 2.) THF-HMPA-hexane, -78 deg C, 1.5 h

With lithium aluminium tetrahydride; n-butyllithium; sodium hydride; methanesulfonyl chloride; triethylamine; lithium bromide; In diethyl ether;

DOI:10.1016/S0040-4020(01)81631-8

Reference yield:

Methyl (4aR,6S,8aS)-6-(benzyloxy)-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalene-1-carboxylate (115333-55-6) → (4aR,6S,8aS)-3,4,4a,5,6,7,8,8a-octahydro-6-benzyloxy-1-<2-(3-furyl)-2-p-tosylethyl>-2,5,5,8a-tetramethylnaphthalene (115626-95-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 59 percent / LAH / diethyl ether / 4 h / Ambient temperature

2: 1.) MsCl, Et₃N; 2.) LiBr / 1.) CH₂Cl₂, -60 deg C, 30 min; 2.) CH₂Cl₂-THF, -60 deg C then -20 deg C 45 min

3: 1.) n-BuLi / 1.) THF-HMPA-hexane, -78 deg C, 20 min; 2.) THF-HMPA-hexane, -78 deg C, 1.5 h

With lithium aluminium tetrahydride; n-butyllithium; methanesulfonyl chloride; triethylamine; lithium bromide; In diethyl ether;

DOI:10.1016/S0040-4020(01)81631-8

upstream raw materials:

3-(tosylmethyl)furan

(3S,4aR,8aS)-3-Benzyloxy-8-bromomethyl-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

methyl (1S,4aR,6S,8aS)-(+)-1,4,4a,5,6,7,8,8a-octahydro-6-hydroxy-2,5,5,8a-tetramethyl-1-naphthalenecarboxylate

benzyl chloride

Downstream raw materials:

(+)-Baiyunol

Refernces