(3aS,6R,6aS)-(3aα,6aα)-2,3,3a,5,6,6a-hexahydro-6α-<2,2-dimethyl-3-(tosyloxy)propyl>-1,4-pentalenedione ethylene ketal

Base Information

• Chemical Name: (3aS,6R,6aS)-(3aα,6aα)-2,3,3a,5,6,6a-hexahydro-6α-<2,2-dimethyl-3-(tosyloxy)propyl>-1,4-pentalenedione ethylene ketal
• CAS No.: 111849-20-8
• Molecular Formula: C₂₃H₃₂O₆S
• Molecular Weight: 436.569
• Mol file: 111849-20-8.mol

Synonyms:(3aS,6R,6aS)-(3aα,6aα)-2,3,3a,5,6,6a-hexahydro-6α-<2,2-dimethyl-3-(tosyloxy)propyl>-1,4-pentalenedione ethylene ketal

Chemical Property of (3aS,6R,6aS)-(3aα,6aα)-2,3,3a,5,6,6a-hexahydro-6α-<2,2-dimethyl-3-(tosyloxy)propyl>-1,4-pentalenedione ethylene ketal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,6R,6aS)-(3aα,6aα)-2,3,3a,5,6,6a-hexahydro-6α-<2,2-dimethyl-3-(tosyloxy)propyl>-1,4-pentalenedione ethylene ketal

There total 11 articles about (3aS,6R,6aS)-(3aα,6aα)-2,3,3a,5,6,6a-hexahydro-6α-<2,2-dimethyl-3-(tosyloxy)propyl>-1,4-pentalenedione ethylene ketal 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: 99.0%

(3aS,6R,6aS)-(3aα,6aα)-2,3,3a,5,6,6a-hexahydro-6α-(2,2-dimethyl-3-hydroxypropyl)-1,4-pentalenedione ethylene ketal (96759-80-7) + p-toluenesulfonyl chloride (98-59-9) → (3aS,6R,6aS)-(3aα,6aα)-2,3,3a,5,6,6a-hexahydro-6α-<2,2-dimethyl-3-(tosyloxy)propyl>-1,4-pentalenedione ethylene ketal (111849-20-8)

Guidance literature:

With pyridine; at 25 ℃; for 20h;

DOI:10.1021/jo00238a007

Reference yield:

1-bromo-3-<(tert-butyldimethylsilyl)oxy>-2,2-dimethylpropane (111849-25-3) → (3aS,6R,6aS)-(3aα,6aα)-2,3,3a,5,6,6a-hexahydro-6α-<2,2-dimethyl-3-(tosyloxy)propyl>-1,4-pentalenedione ethylene ketal (111849-20-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) Li, CuI*Me₂S / 1.) RT; ether; 2.) ether, -30 deg C, 1 h

2: n-Bu₄NF / tetrahydrofuran / 15 h / Ambient temperature

3: pyridine / 20 h / Ambient temperature

With pyridine; copper(I) iodide dimethyl sulfide complex; tetrabutyl ammonium fluoride; lithium; In tetrahydrofuran;

DOI:10.1021/ja00299a061

Reference yield:

3-bromo-2,2-dimethyl-propan-1-ol (40894-00-6) → (3aS,6R,6aS)-(3aα,6aα)-2,3,3a,5,6,6a-hexahydro-6α-<2,2-dimethyl-3-(tosyloxy)propyl>-1,4-pentalenedione ethylene ketal (111849-20-8)

Guidance literature:

Multi-step reaction with 4 steps

1: Et₃N, DMAP / CH₂Cl₂

2: 1.) Li, CuI*Me₂S / 1.) RT; ether; 2.) ether, -30 deg C, 1 h

3: n-Bu₄NF / tetrahydrofuran / 15 h / Ambient temperature

4: pyridine / 20 h / Ambient temperature

With pyridine; dmap; copper(I) iodide dimethyl sulfide complex; tetrabutyl ammonium fluoride; lithium; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00299a061

upstream raw materials:

(3aS,6R,6aS)-(3aα,6aα)-2,3,3a,5,6,6a-hexahydro-6α-(2,2-dimethyl-3-hydroxypropyl)-1,4-pentalenedione ethylene ketal

p-toluenesulfonyl chloride

3-bromo-2,2-dimethyl-propan-1-ol

1-bromo-3-<(tert-butyldimethylsilyl)oxy>-2,2-dimethylpropane

Downstream raw materials:

(+)-hirsutene