<1S-(1α,2β,3α,5α)>-2-(methoxymethyl)-3,5-bis(phenylmethoxy)cyclopentanemethanol

Base Information

• Chemical Name: <1S-(1α,2β,3α,5α)>-2-(methoxymethyl)-3,5-bis(phenylmethoxy)cyclopentanemethanol
• CAS No.: 115859-30-8
• Molecular Formula: C₂₂H₂₈O₄
• Molecular Weight: 356.462

Synonyms:<1S-(1α,2β,3α,5α)>-2-(methoxymethyl)-3,5-bis(phenylmethoxy)cyclopentanemethanol

Chemical Property of <1S-(1α,2β,3α,5α)>-2-(methoxymethyl)-3,5-bis(phenylmethoxy)cyclopentanemethanol

Chemical Property:

Purity/Quality:

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Technology Process of <1S-(1α,2β,3α,5α)>-2-(methoxymethyl)-3,5-bis(phenylmethoxy)cyclopentanemethanol

There total 12 articles about <1S-(1α,2β,3α,5α)>-2-(methoxymethyl)-3,5-bis(phenylmethoxy)cyclopentanemethanol 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: 65.0%

<(2R)-(2α,4aβ,5β,6α,7aβ)>-hexahydro-5-(methoxymethyl)-2-phenyl-6-(phenylmethoxy)cyclopenta-1,3-dioxin (106139-77-9) → <1S-(1α,2α,3β,4α)>-3-(methoxymethyl)-4-(phenylmethoxy)-2-<(phenylmethoxy)methyl>cyclopentanol (115859-29-5) + <1S-(1α,2β,3α,5α)>-2-(methoxymethyl)-3,5-bis(phenylmethoxy)cyclopentanemethanol (115859-30-8)

Guidance literature:

With lithium aluminium tetrahydride; aluminium trichloride; In diethyl ether; dichloromethane; for 1h; Ambient temperature;

DOI:10.1021/jo00254a020

Reference yield:

(3aα,4α,5β,6aα)-(-)-hexahydro-4-(methoxymethyl)-5-<(4-phenylphenyl)carboxy>-2H-cyclopentafuran-2-one (38361-00-1) → <1S-(1α,2β,3α,5α)>-2-(methoxymethyl)-3,5-bis(phenylmethoxy)cyclopentanemethanol (115859-30-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 40 percent / LAH / tetrahydrofuran / 1 h / 5 - 25 °C

2: 4-(dimethylamino)pyridine, pyridine / 96 h / Ambient temperature

3: NaH / dimethylformamide / 1.5 h / 0 °C

4: 73 percent / aq. CH₃COOH / Ambient temperature

5: pyridine, tri-n-butylphosphine / 90 h / Ambient temperature

6: 30percent H₂O₂ / tetrahydrofuran / 2 h

With pyridine; dmap; lithium aluminium tetrahydride; tributylphosphine; dihydrogen peroxide; sodium hydride; acetic acid; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo00254a020

Reference yield:

(-)-Corey lactone 5-(4-phenylbenzoate) (31752-99-5) → <1S-(1α,2β,3α,5α)>-2-(methoxymethyl)-3,5-bis(phenylmethoxy)cyclopentanemethanol (115859-30-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 36 percent / NaH / dimethylformamide / 0.5 h / 0 °C

2: 40 percent / LAH / tetrahydrofuran / 1 h / 5 - 25 °C

3: 4-(dimethylamino)pyridine, pyridine / 96 h / Ambient temperature

4: NaH / dimethylformamide / 1.5 h / 0 °C

5: 73 percent / aq. CH₃COOH / Ambient temperature

6: pyridine, tri-n-butylphosphine / 90 h / Ambient temperature

7: 30percent H₂O₂ / tetrahydrofuran / 2 h

With pyridine; dmap; lithium aluminium tetrahydride; tributylphosphine; dihydrogen peroxide; sodium hydride; acetic acid; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo00254a020

upstream raw materials:

C₂₃H₂₈O₃

<(2R)-(2α,4aβ,5β,6α,7aβ)>-hexahydro-5-(methoxymethyl)-2-phenyl-6-(phenylmethoxy)cyclopenta-1,3-dioxin

(-)-Corey lactone 5-(4-phenylbenzoate)

(3aα,4α,5β,6aα)-(-)-hexahydro-4-(methoxymethyl)-5-<(4-phenylphenyl)carboxy>-2H-cyclopentafuran-2-one

Downstream raw materials:

Toluene-4-sulfonic acid (1S,2S,3R,5S)-3,5-bis-benzyloxy-2-methoxymethyl-cyclopentylmethyl ester

<1R-(1α,2β,3α,5α)>-2-methoxymethyl-3,5-bis(phenylmethoxy)cyclopentaneacetonitrile

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