(3S,5S)-5-[(1R)-2-(benzyloxy)-1-hydroxyethyl]-3-isopropyldihydrofuran-2(3H)-one

Base Information

Chemical Name:(3S,5S)-5-[(1R)-2-(benzyloxy)-1-hydroxyethyl]-3-isopropyldihydrofuran-2(3H)-one
CAS No.:1056674-54-4
Molecular Formula:C₁₆H₂₂O₄
Molecular Weight:278.348
Hs Code.:

Synonyms:(3S,5S)-5-[(1R)-2-(benzyloxy)-1-hydroxyethyl]-3-isopropyldihydrofuran-2(3H)-one

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Chemical Property of (3S,5S)-5-[(1R)-2-(benzyloxy)-1-hydroxyethyl]-3-isopropyldihydrofuran-2(3H)-one

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Technology Process of (3S,5S)-5-[(1R)-2-(benzyloxy)-1-hydroxyethyl]-3-isopropyldihydrofuran-2(3H)-one

There total 18 articles about (3S,5S)-5-[(1R)-2-(benzyloxy)-1-hydroxyethyl]-3-isopropyldihydrofuran-2(3H)-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: 79.0%

: 1056674-45-3
(3S,5S)-5-((R)-1,2-dihydroxyethyl)-3-isopropyldihydrofuran-2(3H)-one

: 100-39-0
benzyl bromide

: 1056674-54-4
(3S,5S)-5-[(1R)-2-(benzyloxy)-1-hydroxyethyl]-3-isopropyldihydrofuran-2(3H)-one

Guidance literature:: (3S,5S)-5-((R)-1,2-dihydroxyethyl)-3-isopropyldihydrofuran-2(3H)-one; With di(n-butyl)tin oxide; In benzene; for 3h; Heating / reflux;

benzyl bromide; With tetrabutylammomium bromide; In benzene; at 80 ℃; Product distribution / selectivity;

Reference yield:

: 1000045-24-8
(2S,4E)-6-(benzyloxy)-2-isopropylhex-4-enoic acid

: 1056674-54-4
(3S,5S)-5-[(1R)-2-(benzyloxy)-1-hydroxyethyl]-3-isopropyldihydrofuran-2(3H)-one

Guidance literature:: With Oxone; Shi's ketone; tetra(n-butyl)ammonium hydrogensulfate; edetate disodium; potassium carbonate; In acetonitrile; at 0 ℃; for 9h;
DOI:10.1016/j.bmc.2013.03.022

Reference yield:

: 1056674-35-1
5,6-di-O-benzyl-2,3-dideoxy-D-glucono-1,4-lactone

: 1056674-54-4
(3S,5S)-5-[(1R)-2-(benzyloxy)-1-hydroxyethyl]-3-isopropyldihydrofuran-2(3H)-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / -60 °C

1.2: 1 h / -60 °C

2.1: hydrogen / palladium 10% on activated carbon / methanol / 2250.23 Torr

3.1: di(n-butyl)tin oxide / toluene / 4 h / Heating / reflux

3.2: 22 h / 90 °C

With hydrogen; di(n-butyl)tin oxide; lithium diisopropyl amide; palladium 10% on activated carbon; In tetrahydrofuran; methanol; toluene;