(1R,2R,5S)-2-Allyloxy-3-hydroxymethyl-5-(4-methoxy-benzyloxy)-cyclopent-3-enol

Base Information

Chemical Name:(1R,2R,5S)-2-Allyloxy-3-hydroxymethyl-5-(4-methoxy-benzyloxy)-cyclopent-3-enol
CAS No.:780789-17-5
Molecular Formula:C₁₇H₂₂O₅
Molecular Weight:306.359
Hs Code.:

Synonyms:(1R,2R,5S)-2-Allyloxy-3-hydroxymethyl-5-(4-methoxy-benzyloxy)-cyclopent-3-enol

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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 (1R,2R,5S)-2-Allyloxy-3-hydroxymethyl-5-(4-methoxy-benzyloxy)-cyclopent-3-enol

Chemical Property:

Purity/Quality:

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Technology Process of (1R,2R,5S)-2-Allyloxy-3-hydroxymethyl-5-(4-methoxy-benzyloxy)-cyclopent-3-enol

There total 7 articles about (1R,2R,5S)-2-Allyloxy-3-hydroxymethyl-5-(4-methoxy-benzyloxy)-cyclopent-3-enol 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:

: 780789-16-4
(1R,2R,5S)-2-Allyloxy-3-(tert-butyl-dimethyl-silanyloxymethyl)-5-(4-methoxy-benzyloxy)-cyclopent-3-enol

: 780789-17-5
(1R,2R,5S)-2-Allyloxy-3-hydroxymethyl-5-(4-methoxy-benzyloxy)-cyclopent-3-enol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;
DOI:10.1016/j.tetlet.2004.07.087

Reference yield:

: cis-3-[[(4-methoxyphenyl)methoxy]methyl]-oxiranemethanol

: 780789-17-5
(1R,2R,5S)-2-Allyloxy-3-hydroxymethyl-5-(4-methoxy-benzyloxy)-cyclopent-3-enol

Guidance literature:: Multi-step reaction with 8 steps

1: IBX; pyridine / dimethylsulfoxide / 45 °C

2: KHMDS / toluene; tetrahydrofuran / -20 - 20 °C

3: 95 percent / OsO₄; NMO / tetrahydrofuran; H₂O / 20 °C

4: 88 percent / imidazole / dimethylformamide / 20 °C

5: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

6: 51 percent / 1,2-dimethoxy-ethane / 0 - 20 °C

7: p-TsOH / -78 - 0 °C

8: TBAF / tetrahydrofuran / 20 °C

With pyridine; 1H-imidazole; osmium(VIII) oxide; N-methyl-2-indolinone; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; Dess-Martin periodane; toluene-4-sulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 2: Wittig reaction;
DOI:10.1016/j.tetlet.2004.07.087

Reference yield:

: (2S,3S)-3-(4-Methoxy-benzyloxymethyl)-oxirane-2-carbaldehyde

: 780789-17-5
(1R,2R,5S)-2-Allyloxy-3-hydroxymethyl-5-(4-methoxy-benzyloxy)-cyclopent-3-enol

Guidance literature:: Multi-step reaction with 7 steps

1: KHMDS / toluene; tetrahydrofuran / -20 - 20 °C

2: 95 percent / OsO₄; NMO / tetrahydrofuran; H₂O / 20 °C

3: 88 percent / imidazole / dimethylformamide / 20 °C

4: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

5: 51 percent / 1,2-dimethoxy-ethane / 0 - 20 °C

6: p-TsOH / -78 - 0 °C

7: TBAF / tetrahydrofuran / 20 °C

With 1H-imidazole; osmium(VIII) oxide; N-methyl-2-indolinone; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; Dess-Martin periodane; toluene-4-sulfonic acid; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1: Wittig reaction;
DOI:10.1016/j.tetlet.2004.07.087