(-)-conduritol F tetraacetate

Base Information

• Chemical Name: (-)-conduritol F tetraacetate
• CAS No.: 172017-20-8
• Molecular Formula: C₁₄H₁₈O₈
• Molecular Weight: 314.292
• Mol file: 172017-20-8.mol

Synonyms:

Chemical Property of (-)-conduritol F tetraacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-conduritol F tetraacetate

There total 5 articles about (-)-conduritol F tetraacetate 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:

D-sorbitol (50-70-4) → (-)-conduritol F tetraacetate (172017-20-8)

Guidance literature:

Multi-step reaction with 8 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

7: 1.) PPTS, 2.) TBAF / 1.) CH₂Cl₂, MeOH, 22 deg C, 2.) THF, 22 deg C

8: pyridine, DMAP

With pyridine; 1H-imidazole; hydrogenchloride; dmap; samarium diiodide; oxalyl dichloride; sulfuric acid; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; 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) → (-)-conduritol F tetraacetate (172017-20-8)

Guidance literature:

Multi-step reaction with 7 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

6: 1.) PPTS, 2.) TBAF / 1.) CH₂Cl₂, MeOH, 22 deg C, 2.) THF, 22 deg C

7: pyridine, DMAP

With pyridine; 1H-imidazole; hydrogenchloride; dmap; samarium diiodide; oxalyl dichloride; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; 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

Reference yield:

(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) → (-)-conduritol F tetraacetate (172017-20-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) PPTS, 2.) TBAF / 1.) CH₂Cl₂, MeOH, 22 deg C, 2.) THF, 22 deg C

2: pyridine, DMAP

With pyridine; dmap; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate;

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

upstream raw materials:

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

acetic anhydride

D-sorbitol

C₂₃H₂₆O₈