3-O-benzyl-4-<(1S,2S)-2-(methoxycarbonyl)-4-methylenecyclopentyl>-1,2-O-isopropylidene-α-D-threo-tetrofuranose

Base Information

Chemical Name:3-O-benzyl-4-<(1S,2S)-2-(methoxycarbonyl)-4-methylenecyclopentyl>-1,2-O-isopropylidene-α-D-threo-tetrofuranose
CAS No.:104636-85-3
Molecular Formula:C₂₂H₂₈O₆
Molecular Weight:388.461
Hs Code.:

Synonyms:3-O-benzyl-4-<(1S,2S)-2-(methoxycarbonyl)-4-methylenecyclopentyl>-1,2-O-isopropylidene-α-D-threo-tetrofuranose

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Chemical Property of 3-O-benzyl-4-<(1S,2S)-2-(methoxycarbonyl)-4-methylenecyclopentyl>-1,2-O-isopropylidene-α-D-threo-tetrofuranose

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Technology Process of 3-O-benzyl-4-<(1S,2S)-2-(methoxycarbonyl)-4-methylenecyclopentyl>-1,2-O-isopropylidene-α-D-threo-tetrofuranose

There total 1 articles about 3-O-benzyl-4-<(1S,2S)-2-(methoxycarbonyl)-4-methylenecyclopentyl>-1,2-O-isopropylidene-α-D-threo-tetrofuranose 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%

: 72047-94-0
[2-(acetoxymethyl)prop-2-enyl]trimethylsilane

: 77399-49-6
methyl (E)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-enofuranuronate

: 104636-85-3
3-O-benzyl-4-<(1S,2S)-2-(methoxycarbonyl)-4-methylenecyclopentyl>-1,2-O-isopropylidene-α-D-threo-tetrofuranose

Guidance literature:: With triisopropyl phosphite; palladium diacetate;
DOI:10.1016/S0040-4039(01)84586-X

Reference yield:

: 104636-85-3
3-O-benzyl-4-<(1S,2S)-2-(methoxycarbonyl)-4-methylenecyclopentyl>-1,2-O-isopropylidene-α-D-threo-tetrofuranose

: [(1S,2S)-2-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-methylene-cyclopentyl]-methanol

Guidance literature:: With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃; for 0.5h;
DOI:10.1055/s-1993-25815

Reference yield:

: 104636-85-3
3-O-benzyl-4-<(1S,2S)-2-(methoxycarbonyl)-4-methylenecyclopentyl>-1,2-O-isopropylidene-α-D-threo-tetrofuranose

: 4-<(1S,2S)-2-benzoyloxymethyl-4-oxocyclopentyl>-1,2-O-isopropylidene-α-D-threo-tetrofuranose

Guidance literature:: Multi-step reaction with 5 steps

1: LiAlH₄ / diethyl ether / 0.5 h / 0 °C

2: pyridine / 1 h / 60 °C

3: OsO₄, 4-methylmorpholine N-oxide, t-BuOOH / acetone; H₂O; 2-methyl-propan-2-ol / 2 h / Ambient temperature

4: NaIO₄ / acetone; H₂O / 3 h / 0 °C

5: 81 percent / H₂ / 10percent Pd-C / acetone / 24 h / Ambient temperature

With pyridine; tert.-butylhydroperoxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; hydrogen; 4-methylmorpholine N-oxide; palladium on activated charcoal; In diethyl ether; water; acetone; tert-butyl alcohol;
DOI:10.1055/s-1993-25815