<3aR-<3aα,4α,5β(S^*),6aα>>-4-<(Benzoyloxy)methyl>-hexahydro-5-<(tetrahydro-2H-pyran-2-yl)oxy>-1H-cyclopentafuran-1-on

Base Information

• Chemical Name: <3aR-<3aα,4α,5β(S^*),6aα>>-4-<(Benzoyloxy)methyl>-hexahydro-5-<(tetrahydro-2H-pyran-2-yl)oxy>-1H-cyclopentafuran-1-on
• CAS No.: 101376-13-0
• Molecular Formula: C₂₀H₂₄O₆
• Molecular Weight: 360.407

Synonyms:

Chemical Property of <3aR-<3aα,4α,5β(S^*),6aα>>-4-<(Benzoyloxy)methyl>-hexahydro-5-<(tetrahydro-2H-pyran-2-yl)oxy>-1H-cyclopentafuran-1-on

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of <3aR-<3aα,4α,5β(S^*),6aα>>-4-<(Benzoyloxy)methyl>-hexahydro-5-<(tetrahydro-2H-pyran-2-yl)oxy>-1H-cyclopentafuran-1-on

There total 7 articles about <3aR-<3aα,4α,5β(S^*),6aα>>-4-<(Benzoyloxy)methyl>-hexahydro-5-<(tetrahydro-2H-pyran-2-yl)oxy>-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:

(3aS-cis)-3,3a,6,6a-Tetrahydro-5-hydroxy-1-oxo-1H-cyclopentafuran-4-carbonsaeure-methylester (88511-03-9) → <3aR-<3aα,4α,5β(S*),6aα>>-4-<(Benzoyloxy)methyl>-hexahydro-5-<(tetrahydro-2H-pyran-2-yl)oxy>-1H-cyclopentafuran-1-on (101376-13-0)

Guidance literature:

Multi-step reaction with 6 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

6: pyridinium-p-toluenesulfonate / CH₂Cl₂ / 4 h / Ambient temperature

With hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; borane-THF; pyridinium p-toluenesulfonate; sodium methylate; In tetrahydrofuran; pyridine; methanol; dichloromethane; water;

DOI:10.1002/jlac.198619860706

Reference yield:

<3aS-(3aα,4β,5β,6aα)>-Hexahydro-5-hydroxy-1-oxo-1H-cyclopentafuran-4-carbonsaeure-methylester (90940-77-5) → <3aR-<3aα,4α,5β(S*),6aα>>-4-<(Benzoyloxy)methyl>-hexahydro-5-<(tetrahydro-2H-pyran-2-yl)oxy>-1H-cyclopentafuran-1-on (101376-13-0)

Guidance literature:

Multi-step reaction with 5 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

5: pyridinium-p-toluenesulfonate / CH₂Cl₂ / 4 h / Ambient temperature

With hydrogenchloride; potassium hydroxide; borane-THF; pyridinium p-toluenesulfonate; sodium methylate; In tetrahydrofuran; pyridine; methanol; dichloromethane; water;

DOI:10.1002/jlac.198619860706

Reference yield:

<3aS-(3aα,4α,5β,6aα)>-Hexahydro-5-hydroxy-1-oxo-1H-cyclopentafuran-4-carbonsaeure (90900-52-0) → <3aR-<3aα,4α,5β(S*),6aα>>-4-<(Benzoyloxy)methyl>-hexahydro-5-<(tetrahydro-2H-pyran-2-yl)oxy>-1H-cyclopentafuran-1-on (101376-13-0)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: pyridinium-p-toluenesulfonate / CH₂Cl₂ / 4 h / Ambient temperature

With borane-THF; pyridinium p-toluenesulfonate; In tetrahydrofuran; pyridine; dichloromethane;

DOI:10.1002/jlac.198619860706

upstream raw materials:

3,4-dihydro-2H-pyran

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

benzoyl chloride

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

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