(3aR*,4aR*,5R*,6R*,8aS*)-3,3a,4,4a,5,7,8,8a,9,10-decahydro-3a,8a-dimethyl-5-<(tosyloxy)methyl>-1-isopropylbenzazulen-6(2H)-ol

Base Information

• Chemical Name: (3aR*,4aR*,5R*,6R*,8aS*)-3,3a,4,4a,5,7,8,8a,9,10-decahydro-3a,8a-dimethyl-5-<(tosyloxy)methyl>-1-isopropylbenzazulen-6(2H)-ol
• CAS No.: 133728-51-5
• Molecular Formula: C₂₇H₄₀O₄S
• Molecular Weight: 460.678
• Mol file: 133728-51-5.mol

Synonyms:

Chemical Property of (3aR*,4aR*,5R*,6R*,8aS*)-3,3a,4,4a,5,7,8,8a,9,10-decahydro-3a,8a-dimethyl-5-<(tosyloxy)methyl>-1-isopropylbenzazulen-6(2H)-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR*,4aR*,5R*,6R*,8aS*)-3,3a,4,4a,5,7,8,8a,9,10-decahydro-3a,8a-dimethyl-5-<(tosyloxy)methyl>-1-isopropylbenzazulen-6(2H)-ol

There total 15 articles about (3aR*,4aR*,5R*,6R*,8aS*)-3,3a,4,4a,5,7,8,8a,9,10-decahydro-3a,8a-dimethyl-5-<(tosyloxy)methyl>-1-isopropylbenzazulen-6(2H)-ol 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: 73.0%

(3aR*,4aR*,5R*,6R*,8aS*)-3,3a,4,4a,5,7,8,8a,9,10-decahydro-3a,8a-dimethyl-5-(hydroxymethyl)-1-isopropylbenzazulen-6(2H)-ol (133728-50-4) + p-toluenesulfonyl chloride (98-59-9) → (3aR*,4aR*,5R*,6R*,8aS*)-3,3a,4,4a,5,7,8,8a,9,10-decahydro-3a,8a-dimethyl-5-<(tosyloxy)methyl>-1-isopropylbenzazulen-6(2H)-ol (133728-51-5)

Guidance literature:

DOI:10.1016/0040-4039(90)80195-R

Reference yield: 20.0%

(3aR*,4aR*,5R*,6R*,8aS*)-3,3a,4,4a,5,7,8,8a,9,10-decahydro-3a,8a-dimethyl-5-(hydroxymethyl)-1-isopropylbenzazulen-6(2H)-ol (133728-50-4) + p-toluenesulfonyl chloride (98-59-9) → (3aR*,4aR*,5R*,6R*,8aS*)-3,3a,4,4a,5,7,8,8a,9,10-decahydro-3a,8a-dimethyl-5-<(tosyloxy)methyl>-1-isopropylbenzazulen-6(2H)-ol (133728-51-5) + C34H46O6S2

Guidance literature:

In pyridine; at 0 ℃; for 18h;

DOI:10.1021/jo00012a035

Reference yield:

2-isopropyl-1,3-cyclopentanedione (824-19-1) → (3aR*,4aR*,5R*,6R*,8aS*)-3,3a,4,4a,5,7,8,8a,9,10-decahydro-3a,8a-dimethyl-5-<(tosyloxy)methyl>-1-isopropylbenzazulen-6(2H)-ol (133728-51-5)

Guidance literature:

Multi-step reaction with 11 steps

1: 95 percent / H⁺

2: 78 percent / LDA

3: 88 percent

4: 2) H₃O⁺

5: 93 percent / ethylaluminium dichloride / 0 °C

6: 88 percent / LAH/AlCl₃

7: 72 percent Turnov_. / Cr(CO)6, tert-butyl hydroperoxide

8: 95 percent / LAH

9: 91 percent

10: 1) n-Bu₃SnH, 2) KF, H₂O₂

11: 73 percent

With tert.-butylhydroperoxide; potassium fluoride; lithium aluminium tetrahydride; aluminium trichloride; oxonium; dihydrogen peroxide; tri-n-butyl-tin hydride; ethylaluminum dichloride; hydrogen cation; chromium⁽⁰⁾ hexacarbonyl; lithium diisopropyl amide;

DOI:10.1016/0040-4039(90)80195-R

upstream raw materials:

(3aR*,4aR*,5R*,6R*,8aS*)-3,3a,4,4a,5,7,8,8a,9,10-decahydro-3a,8a-dimethyl-5-(hydroxymethyl)-1-isopropylbenzazulen-6(2H)-ol

p-toluenesulfonyl chloride

2-isopropyl-1,3-cyclopentanedione

2-carbomethoxy-2-cyclohexenone

Downstream raw materials:

14-deoxyisoamijiol

(3aR,4aS,8aS)-5-Benzenesulfinylmethyl-1-isopropyl-3a,8a-dimethyl-2,3,3a,4,4a,7,8,8a,9,10-decahydro-benzo[f]azulene

(3aR*,4aR*,5R*,6R*,8aS*)-2,3a,4,4a,5,7,8,8a,9,10-decahydro-3a,8a-dimethyl-5-methylene-1-isopropylbenzazulen-6(3H)-ol