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

Base Information

Chemical Name:3-O-benzyl-4-<(1S,2S)-2-benzoyloxymethyl-4-oxocyclopentyl>-1,2-O-isopropylidene-α-D-threo-tetrofuranose
CAS No.:146984-61-4
Molecular Formula:C₂₇H₃₀O₇
Molecular Weight:466.531
Hs Code.:

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

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

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

There total 5 articles about 3-O-benzyl-4-<(1S,2S)-2-benzoyloxymethyl-4-oxocyclopentyl>-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:

: Benzoic acid (1S,2S)-2-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-4-hydroxy-4-hydroxymethyl-cyclopentylmethyl ester

: 146984-61-4
3-O-benzyl-4-<(1S,2S)-2-benzoyloxymethyl-4-oxocyclopentyl>-1,2-O-isopropylidene-α-D-threo-tetrofuranose

Guidance literature:: With sodium periodate; In water; acetone; at 0 ℃; for 3h; Yield given;
DOI:10.1055/s-1993-25815

Reference yield:

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

: 146984-61-4
3-O-benzyl-4-<(1S,2S)-2-benzoyloxymethyl-4-oxocyclopentyl>-1,2-O-isopropylidene-α-D-threo-tetrofuranose

Guidance literature:: Multi-step reaction with 5 steps

1: 85 percent / Pd(OAc)2, P(OPr-i)3 / toluene / 24 h / 80 °C

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

3: pyridine / 1 h / 60 °C

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

5: NaIO₄ / acetone; H₂O / 3 h / 0 °C

With pyridine; tert.-butylhydroperoxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; 4-methylmorpholine N-oxide; palladium diacetate; triisopropyl phosphite; In diethyl ether; water; acetone; toluene; tert-butyl alcohol;
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

: 146984-61-4
3-O-benzyl-4-<(1S,2S)-2-benzoyloxymethyl-4-oxocyclopentyl>-1,2-O-isopropylidene-α-D-threo-tetrofuranose

Guidance literature:: Multi-step reaction with 4 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

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