(-)-(1R,4S,5S)-1-benzoyloxy-3-[(benzyloxy)methyl]-4,5-(isopropylidenedioxy)-2-cyclopentene

Base Information

Chemical Name:(-)-(1R,4S,5S)-1-benzoyloxy-3-[(benzyloxy)methyl]-4,5-(isopropylidenedioxy)-2-cyclopentene
CAS No.:945915-32-2
Molecular Formula:C₂₃H₂₄O₅
Molecular Weight:380.441
Hs Code.:

Synonyms:(-)-(1R,4S,5S)-1-benzoyloxy-3-[(benzyloxy)methyl]-4,5-(isopropylidenedioxy)-2-cyclopentene

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Chemical Property of (-)-(1R,4S,5S)-1-benzoyloxy-3-[(benzyloxy)methyl]-4,5-(isopropylidenedioxy)-2-cyclopentene

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Technology Process of (-)-(1R,4S,5S)-1-benzoyloxy-3-[(benzyloxy)methyl]-4,5-(isopropylidenedioxy)-2-cyclopentene

There total 4 articles about (-)-(1R,4S,5S)-1-benzoyloxy-3-[(benzyloxy)methyl]-4,5-(isopropylidenedioxy)-2-cyclopentene 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: 82.0%

: 945915-31-1
(-)-(1S,4R,5R)-1-benzoyloxy-1-[(benzyloxy)methyl]-4,5-(isopropylidenedioxy)-3-cyclopentene

: 945915-32-2
(-)-(1R,4S,5S)-1-benzoyloxy-3-[(benzyloxy)methyl]-4,5-(isopropylidenedioxy)-2-cyclopentene

Guidance literature:: With p-benzoquinone; PdCl₂[CH₃CN]2; In tetrahydrofuran; for 24h; Heating;
DOI:10.1016/j.tet.2007.04.094

Reference yield:

: 945915-30-0
(-)-(1S,4R,5R)-1-[(benzyloxy)methyl]-4,5-(isopropylidenedioxy)-3-cyclopenten-1-ol

: 945915-32-2
(-)-(1R,4S,5S)-1-benzoyloxy-3-[(benzyloxy)methyl]-4,5-(isopropylidenedioxy)-2-cyclopentene

Guidance literature:: Multi-step reaction with 2 steps

1: 72 percent / pyridine / 20 °C

2: 82 percent / p-benzoquinone / PdCl₂[CH₃CN]2 / tetrahydrofuran / 24 h / Heating

With pyridine; p-benzoquinone; PdCl₂[CH₃CN]2; In tetrahydrofuran;
DOI:10.1016/j.tet.2007.04.094

Reference yield:

: 115509-13-2
(3aR,6aR)-2,2-Dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one

: 945915-32-2
(-)-(1R,4S,5S)-1-benzoyloxy-3-[(benzyloxy)methyl]-4,5-(isopropylidenedioxy)-2-cyclopentene

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran / 0.33 h / -78 °C

1.2: 74 percent / tetrahydrofuran / 1.33 h / -78 °C

2.1: 72 percent / pyridine / 20 °C

3.1: 82 percent / p-benzoquinone / PdCl₂[CH₃CN]2 / tetrahydrofuran / 24 h / Heating

With pyridine; n-butyllithium; p-benzoquinone; PdCl₂[CH₃CN]2; In tetrahydrofuran;
DOI:10.1016/j.tet.2007.04.094