<3aR-(3aα,4α,5β,6aα)>-4-<(Benzoyloxy)methyl>-hexahydro-5-hydroxy-1H-cyclopentafuran-1-on

Base Information

Chemical Name:<3aR-(3aα,4α,5β,6aα)>-4-<(Benzoyloxy)methyl>-hexahydro-5-hydroxy-1H-cyclopentafuran-1-on
CAS No.:101376-11-8
Molecular Formula:C₁₅H₁₆O₅
Molecular Weight:276.289
Hs Code.:

<3aR-(3aα,4α,5β,6aα)>-4-<(Benzoyloxy)methyl>-hexahydro-5-hydroxy-1H-cyclopenta<c>furan-1-on

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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-(3aα,4α,5β,6aα)>-4-<(Benzoyloxy)methyl>-hexahydro-5-hydroxy-1H-cyclopentafuran-1-on

Chemical Property:

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Technology Process of <3aR-(3aα,4α,5β,6aα)>-4-<(Benzoyloxy)methyl>-hexahydro-5-hydroxy-1H-cyclopentafuran-1-on

There total 5 articles about <3aR-(3aα,4α,5β,6aα)>-4-<(Benzoyloxy)methyl>-hexahydro-5-hydroxy-1H-cyclopentafuran-1-on 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: 14.0%

: 98-88-4
benzoyl chloride

: 90900-53-1
<3aR-(3aα,4α,5β,6aα)>-Hexahydro-4-(hydroxymethyl)-5-hydroxy-1H-cyclopentafuran-1-on

: 101376-11-8
<3aR-(3aα,4α,5β,6aα)>-4-<(Benzoyloxy)methyl>-hexahydro-5-hydroxy-1H-cyclopentafuran-1-on

: 101376-12-9
<3aR-(3aα,4α,5β,6aα)>-5-(Benzoyloxy)-4-<(benzoyloxy)methyl>-hexahydro-1H-cyclopentafuran-1-on

Guidance literature:: In pyridine; at -20 ℃; for 2h;
DOI:10.1002/jlac.198619860706

Reference yield:

: 88511-03-9
(3aS-cis)-3,3a,6,6a-Tetrahydro-5-hydroxy-1-oxo-1H-cyclopentafuran-4-carbonsaeure-methylester

: 101376-11-8
<3aR-(3aα,4α,5β,6aα)>-4-<(Benzoyloxy)methyl>-hexahydro-5-hydroxy-1H-cyclopentafuran-1-on

Guidance literature:: Multi-step reaction with 5 steps

1: NaBH₄ / methanol / 1 h / -70 °C

2: 40 mg / CH₃ONa / methanol / 18 h / Ambient temperature

3: KOH,HCl / H₂O; tetrahydrofuran / 14.3 h / 0 deg C, 30 min; room temp., 14 h

4: 32 percent / borane-THF / tetrahydrofuran / 1.) -15 deg C, 1h 2.) room temp., 8h

5: 73 percent / pyridine / 2 h / -20 °C

With hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; borane-THF; sodium methylate; In tetrahydrofuran; pyridine; methanol; water;
DOI:10.1002/jlac.198619860706

Reference yield:

: 90940-77-5
<3aS-(3aα,4β,5β,6aα)>-Hexahydro-5-hydroxy-1-oxo-1H-cyclopentafuran-4-carbonsaeure-methylester

: 101376-11-8
<3aR-(3aα,4α,5β,6aα)>-4-<(Benzoyloxy)methyl>-hexahydro-5-hydroxy-1H-cyclopentafuran-1-on

Guidance literature:: Multi-step reaction with 4 steps

1: 40 mg / CH₃ONa / methanol / 18 h / Ambient temperature

2: KOH,HCl / H₂O; tetrahydrofuran / 14.3 h / 0 deg C, 30 min; room temp., 14 h

3: 32 percent / borane-THF / tetrahydrofuran / 1.) -15 deg C, 1h 2.) room temp., 8h

4: 73 percent / pyridine / 2 h / -20 °C

With hydrogenchloride; potassium hydroxide; borane-THF; sodium methylate; In tetrahydrofuran; pyridine; methanol; water;
DOI:10.1002/jlac.198619860706