Benzoic acid (3S,3aR,6S,6aR)-6-hydroxy-hexahydro-furo[3,2-b]furan-3-ylmethyl ester

Base Information

Chemical Name:Benzoic acid (3S,3aR,6S,6aR)-6-hydroxy-hexahydro-furo[3,2-b]furan-3-ylmethyl ester
CAS No.:204909-77-3
Molecular Formula:C₁₄H₁₆O₅
Molecular Weight:264.278
Hs Code.:

Synonyms:Benzoic acid (3S,3aR,6S,6aR)-6-hydroxy-hexahydro-furo[3,2-b]furan-3-ylmethyl ester

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of Benzoic acid (3S,3aR,6S,6aR)-6-hydroxy-hexahydro-furo[3,2-b]furan-3-ylmethyl ester

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Technology Process of Benzoic acid (3S,3aR,6S,6aR)-6-hydroxy-hexahydro-furo[3,2-b]furan-3-ylmethyl ester

There total 5 articles about Benzoic acid (3S,3aR,6S,6aR)-6-hydroxy-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: 99.0%

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

: 204909-77-3
Benzoic acid (3S,3aR,6S,6aR)-6-hydroxy-hexahydro-furo[3,2-b]furan-3-ylmethyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 2h; Ambient temperature;
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

: 204909-77-3
Benzoic acid (3S,3aR,6S,6aR)-6-hydroxy-hexahydro-furo[3,2-b]furan-3-ylmethyl ester

Guidance literature:: Multi-step reaction with 5 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

5: 99 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature

With sodium hydroxide; dimethylsulfide borane complex; potassium tert-butylate; tetrabutyl ammonium fluoride; dihydrogen peroxide; pyridinium chlorochromate; In tetrahydrofuran; 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

: 204909-77-3
Benzoic acid (3S,3aR,6S,6aR)-6-hydroxy-hexahydro-furo[3,2-b]furan-3-ylmethyl ester

Guidance literature:: Multi-step reaction with 4 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

4: 99 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature

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