(2S,3S,4R,5R,6R)-5-Methoxy-6-[(2R,4R,5R)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4-dimethyl-heptane-1,3-diol

Base Information

Chemical Name:(2S,3S,4R,5R,6R)-5-Methoxy-6-[(2R,4R,5R)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4-dimethyl-heptane-1,3-diol
CAS No.:474333-89-6
Molecular Formula:C₂₂H₃₆O₆
Molecular Weight:396.524
Hs Code.:

Synonyms:(2S,3S,4R,5R,6R)-5-Methoxy-6-[(2R,4R,5R)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4-dimethyl-heptane-1,3-diol

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Chemical Property of (2S,3S,4R,5R,6R)-5-Methoxy-6-[(2R,4R,5R)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4-dimethyl-heptane-1,3-diol

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Technology Process of (2S,3S,4R,5R,6R)-5-Methoxy-6-[(2R,4R,5R)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4-dimethyl-heptane-1,3-diol

There total 9 articles about (2S,3S,4R,5R,6R)-5-Methoxy-6-[(2R,4R,5R)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4-dimethyl-heptane-1,3-diol 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:

: 18295-66-4
1-ethoxy-1-(trimethylsiloxy)ethene

: C₃₀H₄₂O₇

: (2R,3R,4S,5S,6S)-5-Methoxy-6-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4-dimethyl-heptane-1,3-diol

: 474333-89-6
(2S,3S,4R,5R,6R)-5-Methoxy-6-[(2R,4R,5R)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4-dimethyl-heptane-1,3-diol

Guidance literature:: 1-ethoxy-1-(trimethylsiloxy)ethene; C₃₀H₄₂O₇; With (N-p-tolylsulfonyl)(1,3,2-oxazaborolidin-5-ones)(C₆H₅CH₂); In dichloromethane; at -60 ℃; for 24h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 18h; Further stages. Title compound not separated from byproducts.;
DOI:10.1021/jo025944g

Reference yield:

: tert-Butyl-((1S,2S)-2-[(2R,4R,5R)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-1-{(R)-1-[(2S,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-ethyl}-propoxy)-dimethyl-silane

: 474333-89-6
(2S,3S,4R,5R,6R)-5-Methoxy-6-[(2R,4R,5R)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4-dimethyl-heptane-1,3-diol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 87 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2.5 h / 20 °C

2.1: 93 percent / KHMDS / tetrahydrofuran; toluene / 15 h / 0 - 20 °C

3.1: (4S)-4-benzyl-2-phenyl-3-tosyl-1,3,2-oxazaborolidin-5-one / CH₂Cl₂ / 24 h / -60 °C

3.2: tetrabutylammonium fluoride / tetrahydrofuran / 18 h / 20 °C

With tetrabutyl ammonium fluoride; potassium hexamethylsilazane; (N-p-tolylsulfonyl)(1,3,2-oxazaborolidin-5-ones)(C₆H₅CH₂); In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/jo025944g

Reference yield:

: (2R,3R,4S)-2-[(2S,4R,5S)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-4-[(2R,4R,5R)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-pentan-3-ol

: 474333-89-6
(2S,3S,4R,5R,6R)-5-Methoxy-6-[(2R,4R,5R)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4-dimethyl-heptane-1,3-diol

Guidance literature:: Multi-step reaction with 2 steps

1.1: 93 percent / KHMDS / tetrahydrofuran; toluene / 15 h / 0 - 20 °C

2.1: (4S)-4-benzyl-2-phenyl-3-tosyl-1,3,2-oxazaborolidin-5-one / CH₂Cl₂ / 24 h / -60 °C

2.2: tetrabutylammonium fluoride / tetrahydrofuran / 18 h / 20 °C

With potassium hexamethylsilazane; (N-p-tolylsulfonyl)(1,3,2-oxazaborolidin-5-ones)(C₆H₅CH₂); In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/jo025944g