(3S,5S,6S)-6-((E)-(S)-4-Benzyloxymethoxy-1-methyl-but-2-enyl)-3,5-dimethyl-tetrahydro-pyran-2-one

Base Information

Chemical Name:(3S,5S,6S)-6-((E)-(S)-4-Benzyloxymethoxy-1-methyl-but-2-enyl)-3,5-dimethyl-tetrahydro-pyran-2-one
CAS No.:103664-64-8
Molecular Formula:C₂₀H₂₈O₄
Molecular Weight:332.44
Hs Code.:

Synonyms:(3S,5S,6S)-6-((E)-(S)-4-Benzyloxymethoxy-1-methyl-but-2-enyl)-3,5-dimethyl-tetrahydro-pyran-2-one

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Chemical Property of (3S,5S,6S)-6-((E)-(S)-4-Benzyloxymethoxy-1-methyl-but-2-enyl)-3,5-dimethyl-tetrahydro-pyran-2-one

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Technology Process of (3S,5S,6S)-6-((E)-(S)-4-Benzyloxymethoxy-1-methyl-but-2-enyl)-3,5-dimethyl-tetrahydro-pyran-2-one

There total 27 articles about (3S,5S,6S)-6-((E)-(S)-4-Benzyloxymethoxy-1-methyl-but-2-enyl)-3,5-dimethyl-tetrahydro-pyran-2-one 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:

: 103563-42-4
(4S,5S,6S)-(E)-9-<(benzyloxy)methoxy>-4,6-dimethyl-7-nonen-5-olide

: 74-88-4
methyl iodide

: 103664-64-8
(3S,5S,6S)-6-((E)-(S)-4-Benzyloxymethoxy-1-methyl-but-2-enyl)-3,5-dimethyl-tetrahydro-pyran-2-one

: 103563-43-5
(3R,5S,6S)-6-((E)-(S)-4-Benzyloxymethoxy-1-methyl-but-2-enyl)-3,5-dimethyl-tetrahydro-pyran-2-one

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; Yield given. Yields of byproduct given;
DOI:10.1016/S0040-4039(00)89230-8

Reference yield:

: 103563-37-7
(3S,4S,5R)-(Z)-8-<(benzyloxy)methoxy>-3,5-dimethyl-3-(trimethylsilyl)-1,6-octadien-4-ol

: 103664-64-8
(3S,5S,6S)-6-((E)-(S)-4-Benzyloxymethoxy-1-methyl-but-2-enyl)-3,5-dimethyl-tetrahydro-pyran-2-one

Guidance literature:: Multi-step reaction with 8 steps

1: 94 percent / PPTS / CH₂Cl₂ / Ambient temperature

2: 1.) dicyclohexyl borane, 2.) H₂O₂ / 1.) THF, 0 deg C

3: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 °C

4: HCl / dioxane / Ambient temperature

5: KH / 1,2-dimethoxy-ethane / 0.5 h / Ambient temperature

6: 0.02N HCl / dioxane / 1 h / Ambient temperature

7: 92 percent / HgCl₂ / acetonitrile; tetrahydrofuran / 1 h / Ambient temperature; pH 7 phosphate buffer

8: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

With hydrogenchloride; oxalyl dichloride; bis(cyclohexanyl)borane; dihydrogen peroxide; pyridinium p-toluenesulfonate; potassium hydride; dimethyl sulfoxide; triethylamine; mercury dichloride; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; dichloromethane; acetonitrile;
DOI:10.1021/ja00277a028

Reference yield:

: 103590-67-6
[(2R,3S,4S)-1-[2-Benzyloxymethoxy-eth-(Z)-ylidene]-2,4-dimethyl-3-(tetrahydro-pyran-2-yloxy)-hex-5-enyl]-trimethyl-silane

: 103664-64-8
(3S,5S,6S)-6-((E)-(S)-4-Benzyloxymethoxy-1-methyl-but-2-enyl)-3,5-dimethyl-tetrahydro-pyran-2-one

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) dicyclohexyl borane, 2.) H₂O₂ / 1.) THF, 0 deg C

2: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 °C

3: HCl / dioxane / Ambient temperature

4: KH / 1,2-dimethoxy-ethane / 0.5 h / Ambient temperature

5: 0.02N HCl / dioxane / 1 h / Ambient temperature

6: 92 percent / HgCl₂ / acetonitrile; tetrahydrofuran / 1 h / Ambient temperature; pH 7 phosphate buffer

7: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

With hydrogenchloride; oxalyl dichloride; bis(cyclohexanyl)borane; dihydrogen peroxide; potassium hydride; dimethyl sulfoxide; triethylamine; mercury dichloride; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; dichloromethane; acetonitrile;
DOI:10.1021/ja00277a028