(4R)-3-benzyl-4-[(1S,2E)-1,4-dihydroxybut-2-enyl]-4-(hydroxymethyl)oxazolidin-2-one

Base Information

Chemical Name:(4R)-3-benzyl-4-[(1S,2E)-1,4-dihydroxybut-2-enyl]-4-(hydroxymethyl)oxazolidin-2-one
CAS No.:1382153-90-3
Molecular Formula:C₁₅H₁₉NO₅
Molecular Weight:293.32
Hs Code.:

Synonyms:(4R)-3-benzyl-4-[(1S,2E)-1,4-dihydroxybut-2-enyl]-4-(hydroxymethyl)oxazolidin-2-one

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Chemical Property of (4R)-3-benzyl-4-[(1S,2E)-1,4-dihydroxybut-2-enyl]-4-(hydroxymethyl)oxazolidin-2-one

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Technology Process of (4R)-3-benzyl-4-[(1S,2E)-1,4-dihydroxybut-2-enyl]-4-(hydroxymethyl)oxazolidin-2-one

There total 9 articles about (4R)-3-benzyl-4-[(1S,2E)-1,4-dihydroxybut-2-enyl]-4-(hydroxymethyl)oxazolidin-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:

: C₁₅H₁₇NO₅

: 1382153-90-3
(4R)-3-benzyl-4-[(1S,2E)-1,4-dihydroxybut-2-enyl]-4-(hydroxymethyl)oxazolidin-2-one

Guidance literature:: With sodium tetrahydroborate; In ethanol; at 0 - 20 ℃; for 0.5h; Inert atmosphere;
DOI:10.1016/j.tetasy.2012.04.012

Reference yield:

: 1382153-84-5
(5R,6S,8S,9R)-6-(acetoxymethyl)-1-benzyl-8,9-dihydroxy-3,7-dioxa-1-azaspiro [4.4]nonan-2-one

: 1382153-90-3
(4R)-3-benzyl-4-[(1S,2E)-1,4-dihydroxybut-2-enyl]-4-(hydroxymethyl)oxazolidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: benzoic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C / Inert atmosphere

2.2: 1.5 h / 0 - 20 °C

3.1: sodium periodate / methanol; water / 0.5 h / 20 °C / Inert atmosphere

4.1: sodium tetrahydroborate / ethanol / 0.5 h / 0 - 20 °C / Inert atmosphere

With sodium tetrahydroborate; sodium periodate; diisobutylaluminium hydride; benzoic acid; In methanol; ethanol; dichloromethane; water; toluene; 1.1: Wittig reaction;
DOI:10.1016/j.tetasy.2012.04.012

Reference yield:

: 1382153-82-3
(3aR,4'S,5S,6aR)-5-(acetoxymethyl)-3'-benzyl-2,2-dimethyldihydro-3aH-spiro[furo[2,3-d][1,3]dioxole-6,4'-oxazolidin]-2'-one

: 1382153-90-3
(4R)-3-benzyl-4-[(1S,2E)-1,4-dihydroxybut-2-enyl]-4-(hydroxymethyl)oxazolidin-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: water; trifluoroacetic acid / 8.5 h / 20 °C / Inert atmosphere

2.1: benzoic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C / Inert atmosphere

3.2: 1.5 h / 0 - 20 °C

4.1: sodium periodate / methanol; water / 0.5 h / 20 °C / Inert atmosphere

5.1: sodium tetrahydroborate / ethanol / 0.5 h / 0 - 20 °C / Inert atmosphere

With sodium tetrahydroborate; sodium periodate; water; diisobutylaluminium hydride; benzoic acid; trifluoroacetic acid; In methanol; ethanol; dichloromethane; water; toluene; 2.1: Wittig reaction;
DOI:10.1016/j.tetasy.2012.04.012