(4S)-4-benzyl-4-(4',6'-di-O-acetyl-2',3'-dideoxy-α-D-erythro-2'-hexenopyranosyl)-2-phenyl-5(4H)-oxazolone

Base Information

Chemical Name:(4S)-4-benzyl-4-(4',6'-di-O-acetyl-2',3'-dideoxy-α-D-erythro-2'-hexenopyranosyl)-2-phenyl-5(4H)-oxazolone
CAS No.:1310709-57-9
Molecular Formula:C₂₆H₂₅NO₇
Molecular Weight:463.487
Hs Code.:

Synonyms:(4S)-4-benzyl-4-(4',6'-di-O-acetyl-2',3'-dideoxy-α-D-erythro-2'-hexenopyranosyl)-2-phenyl-5(4H)-oxazolone

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (4S)-4-benzyl-4-(4',6'-di-O-acetyl-2',3'-dideoxy-α-D-erythro-2'-hexenopyranosyl)-2-phenyl-5(4H)-oxazolone

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Technology Process of (4S)-4-benzyl-4-(4',6'-di-O-acetyl-2',3'-dideoxy-α-D-erythro-2'-hexenopyranosyl)-2-phenyl-5(4H)-oxazolone

There total 4 articles about (4S)-4-benzyl-4-(4',6'-di-O-acetyl-2',3'-dideoxy-α-D-erythro-2'-hexenopyranosyl)-2-phenyl-5(4H)-oxazolone 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: 90.0%

: 5874-61-3,21453-79-2,51127-19-6,75658-67-2
4-benzyl-2-phenyl-2-oxazolin-5-one

: 137122-02-2
1'-O-tert-butoxycarbonyl-4',6'-di-O-acetyl-2',3'-dideoxy-α-D-erythro-2'-hexenopyranoside

: 1310709-57-9
(4S)-4-benzyl-4-(4',6'-di-O-acetyl-2',3'-dideoxy-α-D-erythro-2'-hexenopyranosyl)-2-phenyl-5(4H)-oxazolone

Guidance literature:: With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; triethylamine; In tetrahydrofuran; at 20 ℃; for 2h; optical yield given as %de; diastereoselective reaction; Molecular sieve;
DOI:10.1021/jo2002962

Reference yield: 73.0%

: 5874-61-3,21453-79-2,51127-19-6,75658-67-2
4-benzyl-2-phenyl-2-oxazolin-5-one

: 137122-02-2
1'-O-tert-butoxycarbonyl-4',6'-di-O-acetyl-2',3'-dideoxy-α-D-erythro-2'-hexenopyranoside

: 1310709-57-9
(4S)-4-benzyl-4-(4',6'-di-O-acetyl-2',3'-dideoxy-α-D-erythro-2'-hexenopyranosyl)-2-phenyl-5(4H)-oxazolone

: 1310709-69-3
(4R)-4-benzyl-4-(4',6'-di-O-acetyl-2',3'-dideoxy-α-D-erythro-2'-hexenopyranosyl)-2-phenyl-5(4H)-oxazolone

Guidance literature:: With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triethylamine; 1,2-bis-(diphenylphosphino)ethane; In tetrahydrofuran; at 20 ℃; for 2.5h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/jo2002962

Reference yield:

: 2873-29-2
D-glucal triacetate

: 1310709-57-9
(4S)-4-benzyl-4-(4',6'-di-O-acetyl-2',3'-dideoxy-α-D-erythro-2'-hexenopyranosyl)-2-phenyl-5(4H)-oxazolone

Guidance literature:: Multi-step reaction with 2 steps

1.1: water; hydroquinone / 1 h / Darkness; Heating

1.2: 0.5 h

2.1: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; triethylamine / tetrahydrofuran / 2 h / 20 °C / Molecular sieve

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; water; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; triethylamine; hydroquinone; In tetrahydrofuran;
DOI:10.1021/jo2002962