(3aS,4R,7S,7aS)-4,7-Bis-(tert-butyl-diphenyl-silanyloxy)-2,2-dimethyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxole

Base Information

• Chemical Name: (3aS,4R,7S,7aS)-4,7-Bis-(tert-butyl-diphenyl-silanyloxy)-2,2-dimethyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxole
• CAS No.: 171916-79-3
• Molecular Formula: C₄₁H₅₀O₄Si₂
• Molecular Weight: 663.017
• Mol file: 171916-79-3.mol

Synonyms:(3aS,4R,7S,7aS)-4,7-Bis-(tert-butyl-diphenyl-silanyloxy)-2,2-dimethyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxole

Chemical Property of (3aS,4R,7S,7aS)-4,7-Bis-(tert-butyl-diphenyl-silanyloxy)-2,2-dimethyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,4R,7S,7aS)-4,7-Bis-(tert-butyl-diphenyl-silanyloxy)-2,2-dimethyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxole

There total 5 articles about (3aS,4R,7S,7aS)-4,7-Bis-(tert-butyl-diphenyl-silanyloxy)-2,2-dimethyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxole 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: 93.0%

(3aR,4S,4aS,7aS,8R,8aR)-4,8-Bis-(tert-butyl-diphenyl-silanyloxy)-6,6-dimethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxole-2-thione → (3aS,4R,7S,7aS)-4,7-Bis-(tert-butyl-diphenyl-silanyloxy)-2,2-dimethyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxole (171916-79-3)

Guidance literature:

With phosphorous acid trimethyl ester; at 110 ℃;

DOI:10.1016/0957-4166(95)00246-L

Reference yield:

D-sorbitol (50-70-4) → (3aS,4R,7S,7aS)-4,7-Bis-(tert-butyl-diphenyl-silanyloxy)-2,2-dimethyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxole (171916-79-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) H₂SO₄, 2.) 70percent aq. AcOH, 3.) pyridine

2: 70 percent / imidazole, DMAP / dimethylformamide / 22 °C

3: 1.) DIBALH, 2.) 3percent aq. HCl / 1.) toluene, -78 deg C

4: 1.) (COCl)2, DMSO, 2.) i-Pr₂NEt, 3.) SmI₂, t-BuOH

5: 85 percent / toluene / 100 °C

6: 93 percent / (MeO)3P / 110 °C

With pyridine; 1H-imidazole; hydrogenchloride; dmap; samarium diiodide; oxalyl dichloride; sulfuric acid; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; tert-butyl alcohol; phosphorous acid trimethyl ester; In N,N-dimethyl-formamide; toluene;

DOI:10.1016/0957-4166(95)00246-L

Reference yield:

C23H26O8 (171916-76-0) → (3aS,4R,7S,7aS)-4,7-Bis-(tert-butyl-diphenyl-silanyloxy)-2,2-dimethyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxole (171916-79-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 70 percent / imidazole, DMAP / dimethylformamide / 22 °C

2: 1.) DIBALH, 2.) 3percent aq. HCl / 1.) toluene, -78 deg C

3: 1.) (COCl)2, DMSO, 2.) i-Pr₂NEt, 3.) SmI₂, t-BuOH

4: 85 percent / toluene / 100 °C

5: 93 percent / (MeO)3P / 110 °C

With 1H-imidazole; hydrogenchloride; dmap; samarium diiodide; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; tert-butyl alcohol; phosphorous acid trimethyl ester; In N,N-dimethyl-formamide; toluene;

DOI:10.1016/0957-4166(95)00246-L

upstream raw materials:

D-sorbitol

C₂₃H₂₆O₈

2,5-bis-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-D-sorbitol

Downstream raw materials:

(-)-conduritol F tetraacetate

(1R,2R,3R,4S)-5-cyclohexene-1,2,3,4-tetrol

Refernces