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

Base Information

• Chemical Name: (3aR,4aS,7aS,7bR)-7a-(benzyloxy)-2,2-dimethylhexahydro-5H-cyclopenta[4,5]furo[2,3-d][1,3]dioxol-5-one
• CAS No.: 136153-00-9
• Molecular Formula: C₁₇H₂₀O₅
• Molecular Weight: 304.343

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

Chemical Property of (3aR,4aS,7aS,7bR)-7a-(benzyloxy)-2,2-dimethylhexahydro-5H-cyclopenta[4,5]furo[2,3-d][1,3]dioxol-5-one

Chemical Property:

Purity/Quality:

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

There total 12 articles about (3aR,4aS,7aS,7bR)-7a-(benzyloxy)-2,2-dimethylhexahydro-5H-cyclopenta[4,5]furo[2,3-d][1,3]dioxol-5-one 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: 98.0%

(3aR,5S,6R,6aR)-6-(benzyloxy)-2,2-dimethyl-6-vinyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde → (3aR,4aS,7aS,7bR)-7a-(benzyloxy)-2,2-dimethylhexahydro-5H-cyclopenta[4,5]furo[2,3-d][1,3]dioxol-5-one (136153-00-9)

Guidance literature:

With bis(norbornadiene)rhodium(l)tetrafluoroborate; o-phenylenebis(diphenylphosphine); In 1,2-dichloro-ethane; at 75 ℃; for 20h; Inert atmosphere;

DOI:10.1055/S-0029-1218650

Reference yield:

benzyl bromide (100-39-0) → (3aR,4aS,7aS,7bR)-7a-(benzyloxy)-2,2-dimethylhexahydro-5H-cyclopenta[4,5]furo[2,3-d][1,3]dioxol-5-one (136153-00-9)

Guidance literature:

Multi-step reaction with 3 steps

1: NaH

2: 1) H+, 2) KIO₄ / 1) MeOH

3: 60 percent / ethylene / <(Ph₃P)2RhCl>2 / CDCl₃ / 15 h / 75 °C

With potassium metaperiodate; ethene; hydrogen cation; sodium hydride; {RhCl(PPh₃)₂}₂; In chloroform-d1;

DOI:10.1016/0040-4039(91)80809-K

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-ribo-3-hexulofuranose (2847-00-9) → (3aR,4aS,7aS,7bR)-7a-(benzyloxy)-2,2-dimethylhexahydro-5H-cyclopenta[4,5]furo[2,3-d][1,3]dioxol-5-one (136153-00-9)

Guidance literature:

Multi-step reaction with 3 steps

1: NaH

2: 1) H+, 2) KIO₄ / 1) MeOH

3: 60 percent / ethylene / <(Ph₃P)2RhCl>2 / CDCl₃ / 15 h / 75 °C

With potassium metaperiodate; ethene; hydrogen cation; sodium hydride; {RhCl(PPh₃)₂}₂; In chloroform-d1;

DOI:10.1016/0040-4039(91)80809-K

upstream raw materials:

benzyl bromide

1,2:5,6-di-O-isopropylidene-α-D-ribo-3-hexulofuranose

(3aR,5R,6R,6aR)-6-Benzyloxy-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxole

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

Downstream raw materials:

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

C₁₇H₂₂O₅

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