(1S,2S,3R,4R,5S)-2-Allyloxy-1-hydroxymethyl-4-(4-methoxy-benzyloxy)-6-oxa-bicyclo[3.1.0]hexan-3-ol

Base Information

Chemical Name:(1S,2S,3R,4R,5S)-2-Allyloxy-1-hydroxymethyl-4-(4-methoxy-benzyloxy)-6-oxa-bicyclo[3.1.0]hexan-3-ol
CAS No.:780789-20-0
Molecular Formula:C₁₇H₂₂O₆
Molecular Weight:322.358
Hs Code.:

Synonyms:(1S,2S,3R,4R,5S)-2-Allyloxy-1-hydroxymethyl-4-(4-methoxy-benzyloxy)-6-oxa-bicyclo[3.1.0]hexan-3-ol

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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 (1S,2S,3R,4R,5S)-2-Allyloxy-1-hydroxymethyl-4-(4-methoxy-benzyloxy)-6-oxa-bicyclo[3.1.0]hexan-3-ol

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Technology Process of (1S,2S,3R,4R,5S)-2-Allyloxy-1-hydroxymethyl-4-(4-methoxy-benzyloxy)-6-oxa-bicyclo[3.1.0]hexan-3-ol

There total 7 articles about (1S,2S,3R,4R,5S)-2-Allyloxy-1-hydroxymethyl-4-(4-methoxy-benzyloxy)-6-oxa-bicyclo[3.1.0]hexan-3-ol 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: 73.0%

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

: 780789-20-0
(1S,2S,3R,4R,5S)-2-Allyloxy-1-hydroxymethyl-4-(4-methoxy-benzyloxy)-6-oxa-bicyclo[3.1.0]hexan-3-ol

Guidance literature:: With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; In dichloromethane; at -20 ℃;
DOI:10.1016/j.tetlet.2004.07.087

Reference yield:

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

: 780789-20-0
(1S,2S,3R,4R,5S)-2-Allyloxy-1-hydroxymethyl-4-(4-methoxy-benzyloxy)-6-oxa-bicyclo[3.1.0]hexan-3-ol

Guidance literature:: Multi-step reaction with 9 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

9: 73 percent / L-(+)-DET; Ti(OiPr)4; TBHP / CH₂Cl₂ / -20 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; osmium(VIII) oxide; N-methyl-2-indolinone; diethyl (2R,3R)-tartrate; 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 / 9: Sharpless epoxidation;
DOI:10.1016/j.tetlet.2004.07.087

Reference yield:

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

: 780789-20-0
(1S,2S,3R,4R,5S)-2-Allyloxy-1-hydroxymethyl-4-(4-methoxy-benzyloxy)-6-oxa-bicyclo[3.1.0]hexan-3-ol

Guidance literature:: Multi-step reaction with 8 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

8: 73 percent / L-(+)-DET; Ti(OiPr)4; TBHP / CH₂Cl₂ / -20 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; osmium(VIII) oxide; N-methyl-2-indolinone; diethyl (2R,3R)-tartrate; 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 / 8: Sharpless epoxidation;
DOI:10.1016/j.tetlet.2004.07.087