Benzoic acid (3S,3aR,6S,6aS)-6-(tert-butyl-dimethyl-silanyloxy)-hexahydro-furo[3,2-b]furan-3-ylmethyl ester

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Chemical Name:Benzoic acid (3S,3aR,6S,6aS)-6-(tert-butyl-dimethyl-silanyloxy)-hexahydro-furo[3,2-b]furan-3-ylmethyl ester
CAS No.:204909-76-2
Molecular Formula:C₂₀H₃₀O₅Si
Molecular Weight:378.541
Hs Code.:

Synonyms:Benzoic acid (3S,3aR,6S,6aS)-6-(tert-butyl-dimethyl-silanyloxy)-hexahydro-furo[3,2-b]furan-3-ylmethyl ester

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Chemical Property of Benzoic acid (3S,3aR,6S,6aS)-6-(tert-butyl-dimethyl-silanyloxy)-hexahydro-furo[3,2-b]furan-3-ylmethyl ester

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Technology Process of Benzoic acid (3S,3aR,6S,6aS)-6-(tert-butyl-dimethyl-silanyloxy)-hexahydro-furo[3,2-b]furan-3-ylmethyl ester

There total 4 articles about Benzoic acid (3S,3aR,6S,6aS)-6-(tert-butyl-dimethyl-silanyloxy)-hexahydro-furo[3,2-b]furan-3-ylmethyl ester 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: 77.0%

: 98-88-4
benzoyl chloride

: 204909-75-1
[(3R,3aR,6S,6aS)-6-(tert-Butyl-dimethyl-silanyloxy)-hexahydro-furo[3,2-b]furan-3-yl]-methanol

: 204909-76-2
Benzoic acid (3S,3aR,6S,6aS)-6-(tert-butyl-dimethyl-silanyloxy)-hexahydro-furo[3,2-b]furan-3-ylmethyl ester

Guidance literature:: In pyridine; at -10 - 20 ℃;
DOI:10.1016/S0040-4020(98)00061-1

Reference yield:

: 204909-70-6
(3R,3aR,6S,6aS)-6-((tert-butyldimethylsilyl)oxy)hexahydrofuro[3,2-b]furan-3-ol

: 204909-76-2
Benzoic acid (3S,3aR,6S,6aS)-6-(tert-butyl-dimethyl-silanyloxy)-hexahydro-furo[3,2-b]furan-3-ylmethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 83 percent / PCC / CH₂Cl₂ / 3 h / Heating

2: 1.) t-BuOK / 1.) benzene, reflux, 1 h, 2.) benzene, 60 deg C, 2 h

3: 1.) BH₃*SMe₂, 2.) H₂O₂, NaOH / 1.) THF, rt, 5 h, 2.) THF, H₂O, rt, 24 h

4: 77 percent / pyridine / -10 - 20 °C

With sodium hydroxide; dimethylsulfide borane complex; potassium tert-butylate; dihydrogen peroxide; pyridinium chlorochromate; In pyridine; dichloromethane;
DOI:10.1016/S0040-4020(98)00061-1

Reference yield:

: 204909-71-7
(3aS,6S,6aS)-6-(tert-Butyl-dimethyl-silanyloxy)-tetrahydro-furo[3,2-b]furan-3-one

: 204909-76-2
Benzoic acid (3S,3aR,6S,6aS)-6-(tert-butyl-dimethyl-silanyloxy)-hexahydro-furo[3,2-b]furan-3-ylmethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) t-BuOK / 1.) benzene, reflux, 1 h, 2.) benzene, 60 deg C, 2 h

2: 1.) BH₃*SMe₂, 2.) H₂O₂, NaOH / 1.) THF, rt, 5 h, 2.) THF, H₂O, rt, 24 h

3: 77 percent / pyridine / -10 - 20 °C

With sodium hydroxide; dimethylsulfide borane complex; potassium tert-butylate; dihydrogen peroxide; In pyridine;
DOI:10.1016/S0040-4020(98)00061-1