2-(4',6'-di-O-acetyl-α-D-mannopyranosyl)-2-benzamido-(2S)-3-phenylpropanoic acid 1',2'-lactone

Base Information

Chemical Name:2-(4',6'-di-O-acetyl-α-D-mannopyranosyl)-2-benzamido-(2S)-3-phenylpropanoic acid 1',2'-lactone
CAS No.:1310709-61-5
Molecular Formula:C₂₆H₂₇NO₉
Molecular Weight:497.502
Hs Code.:

Synonyms:2-(4',6'-di-O-acetyl-α-D-mannopyranosyl)-2-benzamido-(2S)-3-phenylpropanoic acid 1',2'-lactone

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Chemical Property of 2-(4',6'-di-O-acetyl-α-D-mannopyranosyl)-2-benzamido-(2S)-3-phenylpropanoic acid 1',2'-lactone

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Technology Process of 2-(4',6'-di-O-acetyl-α-D-mannopyranosyl)-2-benzamido-(2S)-3-phenylpropanoic acid 1',2'-lactone

There total 2 articles about 2-(4',6'-di-O-acetyl-α-D-mannopyranosyl)-2-benzamido-(2S)-3-phenylpropanoic acid 1',2'-lactone 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: 78.0%

: 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

: 1310709-61-5
2-(4',6'-di-O-acetyl-α-D-mannopyranosyl)-2-benzamido-(2S)-3-phenylpropanoic acid 1',2'-lactone

Guidance literature:: With osmium(VIII) oxide; water; 4-methylmorpholine N-oxide; In acetone; tert-butyl alcohol; at 20 ℃; for 24h; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/jo2002962

Reference yield:

: 2873-29-2
D-glucal triacetate

: 1310709-61-5
2-(4',6'-di-O-acetyl-α-D-mannopyranosyl)-2-benzamido-(2S)-3-phenylpropanoic acid 1',2'-lactone

Guidance literature:: Multi-step reaction with 3 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

3.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone; tert-butyl alcohol / 24 h / 20 °C / Inert atmosphere

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; osmium(VIII) oxide; water; 4-methylmorpholine N-oxide; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; triethylamine; hydroquinone; In tetrahydrofuran; acetone; tert-butyl alcohol;
DOI:10.1021/jo2002962

Reference yield: 73.0%

: 1310709-61-5
2-(4',6'-di-O-acetyl-α-D-mannopyranosyl)-2-benzamido-(2S)-3-phenylpropanoic acid 1',2'-lactone

: 1310709-64-8
2-(α-D-C-mannopyranosyl)-(S)-N-benzoylphenylalanine methyl ester

Guidance literature:: 2-(4',6'-di-O-acetyl-α-D-mannopyranosyl)-2-benzamido-(2S)-3-phenylpropanoic acid 1',2'-lactone; With sodium methylate; In methanol; at 20 ℃; Inert atmosphere;

With hydrogenchloride; In methanol; water; Inert atmosphere;
DOI:10.1021/jo2002962