(3aR,4S,7R,7aS,8aS,8bR)-4-<(1R)-4-(tert-butyldiphenylsiloxy)-1-methylbutyl>octahydro-7-methyl-1H-cyclopropa<3,4>cycloocta<1,2-c>furan-1,5(2H)-dione

Base Information

• Chemical Name: (3aR,4S,7R,7aS,8aS,8bR)-4-<(1R)-4-(tert-butyldiphenylsiloxy)-1-methylbutyl>octahydro-7-methyl-1H-cyclopropa<3,4>cycloocta<1,2-c>furan-1,5(2H)-dione
• CAS No.: 162789-41-5
• Molecular Formula: C₃₃H₄₄O₄Si
• Molecular Weight: 532.795
• Mol file: 162789-41-5.mol

Synonyms:(3aR,4S,7R,7aS,8aS,8bR)-4-<(1R)-4-(tert-butyldiphenylsiloxy)-1-methylbutyl>octahydro-7-methyl-1H-cyclopropa<3,4>cycloocta<1,2-c>furan-1,5(2H)-dione

Chemical Property of (3aR,4S,7R,7aS,8aS,8bR)-4-<(1R)-4-(tert-butyldiphenylsiloxy)-1-methylbutyl>octahydro-7-methyl-1H-cyclopropa<3,4>cycloocta<1,2-c>furan-1,5(2H)-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4S,7R,7aS,8aS,8bR)-4-<(1R)-4-(tert-butyldiphenylsiloxy)-1-methylbutyl>octahydro-7-methyl-1H-cyclopropa<3,4>cycloocta<1,2-c>furan-1,5(2H)-dione

There total 1 articles about (3aR,4S,7R,7aS,8aS,8bR)-4-<(1R)-4-(tert-butyldiphenylsiloxy)-1-methylbutyl>octahydro-7-methyl-1H-cyclopropa<3,4>cycloocta<1,2-c>furan-1,5(2H)-dione 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: 92.0%

diiodomethane (75-11-6) + (3aR,4S,7R,9aR)-4-<(1R)-4-(tert-butyldiphenylsiloxy)-1-methylbutyl>-3a,4,7,9a-tetrahydro-7-methylcyclooctafuran-1,5(3H,6H)-dione → (3aR,4S,7R,7aS,8aS,8bR)-4-<(1R)-4-(tert-butyldiphenylsiloxy)-1-methylbutyl>octahydro-7-methyl-1H-cyclopropa<3,4>cycloocta<1,2-c>furan-1,5(2H)-dione (162789-41-5)

Guidance literature:

With diethylzinc; In benzene;

DOI:10.1021/ja00109a041

Reference yield: 91.0%

(3aR,4S,7R,7aS,8aS,8bR)-4-<(1R)-4-(tert-butyldiphenylsiloxy)-1-methylbutyl>octahydro-7-methyl-1H-cyclopropa<3,4>cycloocta<1,2-c>furan-1,5(2H)-dione (162789-41-5) → (1R,2S,4S,5R,7R,8S,9R)-8-[(R)-4-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-butyl]-5-methyl-11-oxa-tricyclo[7.3.0.02,4]dodecane-7,12-diol

Guidance literature:

With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 15h;

DOI:10.1021/ja9533609

Reference yield:

(3aR,4S,7R,7aS,8aS,8bR)-4-<(1R)-4-(tert-butyldiphenylsiloxy)-1-methylbutyl>octahydro-7-methyl-1H-cyclopropa<3,4>cycloocta<1,2-c>furan-1,5(2H)-dione (162789-41-5) → (3aR,4S,5R,7R,7aS,8aS,8bR)-4-<(1R)-4-(tert-butyldiphenylsiloxy)-1-methylbutyl>decahydro-5-hydroxy-7-methyl-1H-cyclopropa<3,4>cycloocta<1,2-c>furan-1-one (173864-66-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / Dibal-H / CH₂Cl₂; hexane / 15 h / -78 °C

2: 100 percent / Ag₂CO₃, Celite / benzene / 0.17 h / Heating

With Celite; diisobutylaluminium hydride; silver carbonate; In hexane; dichloromethane; benzene;

DOI:10.1021/ja9533609

upstream raw materials:

diiodomethane

Downstream raw materials:

(3aR,4S,5R,7R,7aS,8aS,8bR)-4-<(1R)-4-(tert-butyldiphenylsiloxy)-1-methylbutyl>decahydro-5-hydroxy-7-methyl-1H-cyclopropa<3,4>cycloocta<1,2-c>furan-1-one

(4S,5R,7R,7aS,8aS)-4-<(1R)-4-(tert-butyldiphenylsiloxy)-1-methylbutyl>-3,4,5,6,7,7a,8,8a-octahydro-5-hydroxy-7-methyl-1H-cyclopropa<3,4>cycloocta<1,2-c>furan-1-one

(4S,5R,7R,7aS,8aS)-4-<(1R)-4-(tert-butyldiphenylsiloxy)-1-methylbutyl>-3,4,5,6,7,7a,8,8a-octahydro-5-hydroxy-7-methyl-1H-cyclopropa<3,4>cycloocta<1,2-c>furan-1-one acetate