(3aR,4aR,5R,7aR,7bR)-7a-(benzyloxy)-2,2-dimethylhexahydro-5H-cyclopenta[4,5]furo[2,3-d][1,3]dioxol-5-ol

Base Information

Chemical Name:(3aR,4aR,5R,7aR,7bR)-7a-(benzyloxy)-2,2-dimethylhexahydro-5H-cyclopenta[4,5]furo[2,3-d][1,3]dioxol-5-ol
CAS No.:1227269-86-4
Molecular Formula:C₁₇H₂₂O₅
Molecular Weight:306.359
Hs Code.:

Synonyms:(3aR,4aR,5R,7aR,7bR)-7a-(benzyloxy)-2,2-dimethylhexahydro-5H-cyclopenta[4,5]furo[2,3-d][1,3]dioxol-5-ol

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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 (3aR,4aR,5R,7aR,7bR)-7a-(benzyloxy)-2,2-dimethylhexahydro-5H-cyclopenta[4,5]furo[2,3-d][1,3]dioxol-5-ol

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Technology Process of (3aR,4aR,5R,7aR,7bR)-7a-(benzyloxy)-2,2-dimethylhexahydro-5H-cyclopenta[4,5]furo[2,3-d][1,3]dioxol-5-ol

There total 11 articles about (3aR,4aR,5R,7aR,7bR)-7a-(benzyloxy)-2,2-dimethylhexahydro-5H-cyclopenta[4,5]furo[2,3-d][1,3]dioxol-5-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: 88.0%

: 136153-00-9
(3aR,4aS,7aS,7bR)-7a-(benzyloxy)-2,2-dimethylhexahydro-5H-cyclopenta[4,5]furo[2,3-d][1,3]dioxol-5-one

: 1227269-86-4
(3aR,4aR,5R,7aR,7bR)-7a-(benzyloxy)-2,2-dimethylhexahydro-5H-cyclopenta[4,5]furo[2,3-d][1,3]dioxol-5-ol

: 1227269-87-5
C₁₇H₂₂O₅

Guidance literature:: With methanol; sodium tetrahydroborate; at 0 ℃; for 1h; Inert atmosphere;
DOI:10.1055/S-0029-1218650

Reference yield: 25.0%

: 136153-00-9
(3aR,4aS,7aS,7bR)-7a-(benzyloxy)-2,2-dimethylhexahydro-5H-cyclopenta[4,5]furo[2,3-d][1,3]dioxol-5-one

: 1227269-86-4
(3aR,4aR,5R,7aR,7bR)-7a-(benzyloxy)-2,2-dimethylhexahydro-5H-cyclopenta[4,5]furo[2,3-d][1,3]dioxol-5-ol

Guidance literature:: With sodium tetrahydroborate; In methanol; at 5 ℃; for 1h;
DOI:10.1021/acs.jmedchem.0c02083

Reference yield:

: 2847-00-9
1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose

: 1227269-86-4
(3aR,4aR,5R,7aR,7bR)-7a-(benzyloxy)-2,2-dimethylhexahydro-5H-cyclopenta[4,5]furo[2,3-d][1,3]dioxol-5-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: tetrahydrofuran / 0.5 h / 0 - 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 15 - 60 °C

2.2: 5 h / 15 - 20 °C

3.1: periodic acid / ethyl acetate / 1 h / 15 - 20 °C

4.1: o-phenylenebis(diphenylphosphine); bis(norbornadiene)rhodium(l)tetrafluoroborate / 1,2-dichloro-ethane / 12.25 h / 15 - 80 °C / Inert atmosphere

5.1: sodium tetrahydroborate; methanol / 1 h / 0 - 5 °C

With methanol; bis(norbornadiene)rhodium(l)tetrafluoroborate; sodium tetrahydroborate; o-phenylenebis(diphenylphosphine); sodium hydride; periodic acid; In tetrahydrofuran; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; mineral oil;