cis-(4R,6R)-2,8-dioxa-4,6-bis(tert-butyldiphenylsilanoxy)-bicyclo[3.3.0]octane

Base Information

• Chemical Name: cis-(4R,6R)-2,8-dioxa-4,6-bis(tert-butyldiphenylsilanoxy)-bicyclo[3.3.0]octane
• CAS No.: 908011-32-5
• Molecular Formula: C₃₈H₄₆O₄Si₂
• Molecular Weight: 622.952
• Mol file: 908011-32-5.mol

Synonyms:cis-(4R,6R)-2,8-dioxa-4,6-bis(tert-butyldiphenylsilanoxy)-bicyclo[3.3.0]octane

Chemical Property of cis-(4R,6R)-2,8-dioxa-4,6-bis(tert-butyldiphenylsilanoxy)-bicyclo[3.3.0]octane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cis-(4R,6R)-2,8-dioxa-4,6-bis(tert-butyldiphenylsilanoxy)-bicyclo[3.3.0]octane

There total 2 articles about cis-(4R,6R)-2,8-dioxa-4,6-bis(tert-butyldiphenylsilanoxy)-bicyclo[3.3.0]octane 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: 79.0%

(4R,6R)-4,6-dihydroxy-2,8-dioxa-bicyclo[3.3.0]octane (908011-31-4) + tert-butylchlorodiphenylsilane (58479-61-1) → cis-(4R,6R)-2,8-dioxa-4,6-bis(tert-butyldiphenylsilanoxy)-bicyclo[3.3.0]octane (908011-32-5)

Guidance literature:

With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 20 ℃; for 24h; Product distribution / selectivity;

Reference yield:

3,4-bis-(tert-butyl-dimethyl-silanyloxy)-hexahydro-furo[2,3-b]furan → cis-(4R,6R)-2,8-dioxa-4,6-bis(tert-butyldiphenylsilanoxy)-bicyclo[3.3.0]octane (908011-32-5)

Guidance literature:

Multi-step reaction with 2 steps

1: NH₄F / methanol / 22 h / Heating

2: 11 percent / 4-(dimethylamino)pyridine; imidazole / dimethylformamide / 24 h / 20 °C

With 1H-imidazole; dmap; ammonium fluoride; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/ol062431d

Reference yield: 40.0%

cis-(4R,6R)-2,8-dioxa-4,6-bis(tert-butyldiphenylsilanoxy)-bicyclo[3.3.0]octane (908011-32-5) → cis-(4R,6R)-2,8-dioxa-4-hydroxy-6-(tert-butyldiphenylsilanoxy)-bicyclo[3.3.0]octane

Guidance literature:

With ammonium fluoride; In methanol; at 20 ℃; for 96h; Product distribution / selectivity;

upstream raw materials:

(4R,6R)-4,6-dihydroxy-2,8-dioxa-bicyclo[3.3.0]octane

tert-butylchlorodiphenylsilane

Downstream raw materials:

(4R,6R)-4,6-dihydroxy-2,8-dioxa-bicyclo[3.3.0]octane

(3R,3aS,4R,6aR)-4-(tert-Butyl-diphenyl-silanyloxy)-hexahydro-furo[2,3-b]furan-3-ol

(3R,3aR,4R,6aS)-4-(tert-Butyl-diphenyl-silanyloxy)-hexahydro-furo[2,3-b]furan-3-ol