(3aα,4β,5α,6β,7α,7aα)-6,7-bis(benzyloxy)-5-fluorohexahydro-2,2-dimethylbenzo-1,3(2H)-dioxol-4-ol

Base Information

• Chemical Name: (3aα,4β,5α,6β,7α,7aα)-6,7-bis(benzyloxy)-5-fluorohexahydro-2,2-dimethylbenzo-1,3(2H)-dioxol-4-ol
• CAS No.: 125291-06-7
• Molecular Formula: C₂₃H₂₇FO₅
• Molecular Weight: 402.463
• Mol file: 125291-06-7.mol

Synonyms:

Chemical Property of (3aα,4β,5α,6β,7α,7aα)-6,7-bis(benzyloxy)-5-fluorohexahydro-2,2-dimethylbenzo-1,3(2H)-dioxol-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aα,4β,5α,6β,7α,7aα)-6,7-bis(benzyloxy)-5-fluorohexahydro-2,2-dimethylbenzo-1,3(2H)-dioxol-4-ol

There total 2 articles about (3aα,4β,5α,6β,7α,7aα)-6,7-bis(benzyloxy)-5-fluorohexahydro-2,2-dimethylbenzo-1,3(2H)-dioxol-4-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: 10.0%

(3aα,4α,5β,6β,7β,7aα)-4,5-bis(benzyloxy)-6,7-epoxyhexahydro-2,2-dimethylbenzo-1,3-dioxole (118993-51-4,130633-17-9,130697-67-5,131435-02-4) → (3aα,4β,5α,6β,7α,7aα)-6,7-bis(benzyloxy)-5-fluorohexahydro-2,2-dimethylbenzo-1,3(2H)-dioxol-4-ol (125291-06-7,130697-80-2) + (3aα,4α,5β,6β,7α,7aα)-6,7-bis(benzyloxy)-4-fluorohexahydro-2,2-dimethylbenzo-1,3(2H)-dioxol-5-ol (125291-07-8,130697-81-3)

Guidance literature:

With tris(dimethylamino)sulfonium trimethylsilyldifluoride; In tetrahydrofuran; for 120h; Heating;

Reference yield:

benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → (3aα,4β,5α,6β,7α,7aα)-6,7-bis(benzyloxy)-5-fluorohexahydro-2,2-dimethylbenzo-1,3(2H)-dioxol-4-ol (125291-06-7,130697-80-2)

Guidance literature:

Multi-step reaction with 2 steps

1: Pseudomonas putida

2: TASF / tetrahydrofuran / 96 h / Heating

With Pseudomonas putida; tris(dimethylamino)sulfonium trimethylsilyldifluoride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)99439-5

Reference yield:

(3aα,4β,5α,6β,7α,7aα)-6,7-bis(benzyloxy)-5-fluorohexahydro-2,2-dimethylbenzo-1,3(2H)-dioxol-4-ol (125291-06-7,130697-80-2) → (1α,2β,3α,4α,5α,6β)-6-fluoro-1,2,3,4,5-cyclohexanepentol 1,2,5-trisphosphate (125356-50-5,130697-84-6,131435-04-6)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / 10percent Pd-C / ethanol / 18 h

2: nBuLi, iPr₂NH / 10percent Pd-C / tetrahydrofuran

3: TMSBr / CH₂Cl₂ / 1.08 h / Ambient temperature

With n-butyllithium; trimethylsilyl bromide; hydrogen; diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1016/S0040-4039(00)99439-5

upstream raw materials:

(3aα,4α,5β,6β,7β,7aα)-4,5-bis(benzyloxy)-6,7-epoxyhexahydro-2,2-dimethylbenzo-1,3-dioxole

benzene

Downstream raw materials:

(1α,2β,3α,4α,5α,6β)-6-fluoro-1,2,3,4,5-cyclohexanepentol 1,2,5-trisphosphate

(3aα,4α,5β,6α,7β,7aα)-6-fluorohexahydro-2,2-dimethylbenzo-1,3(2H)-dioxol-4,5,7-triol tris(dibenzylphosphate)

(1α,2α,3α,4β,5α,6β)-6-fluoro-1,2,3,4,5-cyclohexanepentol