ethyl {(4R,6S)-6-[(S)-2-(benzyloxy)-1-methylethyl]-2-phenyl-1,3-dioxan-4-yl}acetate

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Chemical Name:ethyl {(4R,6S)-6-[(S)-2-(benzyloxy)-1-methylethyl]-2-phenyl-1,3-dioxan-4-yl}acetate
CAS No.:263011-60-5
Molecular Formula:C₂₄H₃₀O₅
Molecular Weight:398.499
Hs Code.:

Synonyms:ethyl {(4R,6S)-6-[(S)-2-(benzyloxy)-1-methylethyl]-2-phenyl-1,3-dioxan-4-yl}acetate

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Chemical Property of ethyl {(4R,6S)-6-[(S)-2-(benzyloxy)-1-methylethyl]-2-phenyl-1,3-dioxan-4-yl}acetate

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Technology Process of ethyl {(4R,6S)-6-[(S)-2-(benzyloxy)-1-methylethyl]-2-phenyl-1,3-dioxan-4-yl}acetate

There total 6 articles about ethyl {(4R,6S)-6-[(S)-2-(benzyloxy)-1-methylethyl]-2-phenyl-1,3-dioxan-4-yl}acetate 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: 79.0%

: 100-52-7
benzaldehyde

: 263011-59-2
ethyl (E)-(5S,6S)-7-(benzyloxy)-5-hydroxy-6-methylhept-2-enoate

: 263011-60-5
ethyl {(4R,6S)-6-[(S)-2-(benzyloxy)-1-methylethyl]-2-phenyl-1,3-dioxan-4-yl}acetate

Guidance literature:: With potassium tert-butylate; In tetrahydrofuran; at 0 ℃;
DOI:10.1016/S0040-4039(99)02169-3

Reference yield:

: 100-52-7
benzaldehyde

: 263011-59-2
ethyl (E)-(5S,6S)-7-(benzyloxy)-5-hydroxy-6-methylhept-2-enoate

: C₂₄H₃₀O₅

: 263011-60-5
ethyl {(4R,6S)-6-[(S)-2-(benzyloxy)-1-methylethyl]-2-phenyl-1,3-dioxan-4-yl}acetate

Guidance literature:: With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 0.75h; optical yield given as %de;
DOI:10.1055/s-2008-1067219

Reference yield:

: 81520-05-0
[(2R,3R)-3-((S)-2-Benzyloxy-1-methyl-ethyl)-oxiranyl]-methanol

: 263011-60-5
ethyl {(4R,6S)-6-[(S)-2-(benzyloxy)-1-methylethyl]-2-phenyl-1,3-dioxan-4-yl}acetate

Guidance literature:: Multi-step reaction with 4 steps

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

2: diphenylselenide; sodium borohydride; acetic acid / ethanol / 1 h / 0 °C

3: NaH / tetrahydrofuran / 0 °C

4: 79 percent / t-BuOK / tetrahydrofuran / 0 °C

With sodium tetrahydroborate; oxalyl dichloride; diphenylselenide; potassium tert-butylate; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; 1: Oxidation / 2: Reduction / 3: Alkylation / 4: Cyclization;
DOI:10.1016/S0040-4039(99)02169-3