ethyl 2-(4',6'-di-O-benzyl-2',3'-dideoxy-β-D-erythro-hex-2'-enopyranosyl)-2-nitro-2-(ethoxycarbonyl)acetate

Base Information

Chemical Name:ethyl 2-(4',6'-di-O-benzyl-2',3'-dideoxy-β-D-erythro-hex-2'-enopyranosyl)-2-nitro-2-(ethoxycarbonyl)acetate
CAS No.:119367-04-3
Molecular Formula:C₂₇H₃₁NO₉
Molecular Weight:513.544
Hs Code.:

Synonyms:ethyl 2-(4',6'-di-O-benzyl-2',3'-dideoxy-β-D-erythro-hex-2'-enopyranosyl)-2-nitro-2-(ethoxycarbonyl)acetate

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Chemical Property of ethyl 2-(4',6'-di-O-benzyl-2',3'-dideoxy-β-D-erythro-hex-2'-enopyranosyl)-2-nitro-2-(ethoxycarbonyl)acetate

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Technology Process of ethyl 2-(4',6'-di-O-benzyl-2',3'-dideoxy-β-D-erythro-hex-2'-enopyranosyl)-2-nitro-2-(ethoxycarbonyl)acetate

There total 5 articles about ethyl 2-(4',6'-di-O-benzyl-2',3'-dideoxy-β-D-erythro-hex-2'-enopyranosyl)-2-nitro-2-(ethoxycarbonyl)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: 93.0%

: 603-67-8
diethyl nitromalonate

: 113019-35-5
phenyl 4,6-di-O-benzyl-2,3-dideoxy-α,β-D-erythro-hex-2-enopyranoside

: 119367-04-3
ethyl 2-(4',6'-di-O-benzyl-2',3'-dideoxy-β-D-erythro-hex-2'-enopyranosyl)-2-nitro-2-(ethoxycarbonyl)acetate

Guidance literature:: With 1,4-di(diphenylphosphino)-butane; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; at 60 ℃; for 6h;
DOI:10.1021/jo00269a026

Reference yield:

: 62398-09-8
Acetic acid (2R,3S,6R)-2-acetoxymethyl-6-phenoxy-3,6-dihydro-2H-pyran-3-yl ester

: 119367-04-3
ethyl 2-(4',6'-di-O-benzyl-2',3'-dideoxy-β-D-erythro-hex-2'-enopyranosyl)-2-nitro-2-(ethoxycarbonyl)acetate

Guidance literature:: Multi-step reaction with 3 steps

1: MeONa / methanol / 0.5 h / 25 °C

2: 1.) KOH / dimethylsulfoxide / 1.) 0 deg C, 15 min, 2.) room temp., 14 h

3: 93 percent / Pd(dba)2/1,4-bis(diphenylphosphino)butane (dppb) / tetrahydrofuran / 6 h / 60 °C

With potassium hydroxide; sodium methylate; 1,4-di(diphenylphosphino)-butane; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; methanol; dimethyl sulfoxide;
DOI:10.1021/jo00269a026

Reference yield:

: 95843-67-7
2,3-Didehydro-2,3-didesoxy-α-D-erythro-(phenyl-hexosid)

: 119367-04-3
ethyl 2-(4',6'-di-O-benzyl-2',3'-dideoxy-β-D-erythro-hex-2'-enopyranosyl)-2-nitro-2-(ethoxycarbonyl)acetate

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) KOH / dimethylsulfoxide / 1.) 0 deg C, 15 min, 2.) room temp., 14 h

2: 93 percent / Pd(dba)2/1,4-bis(diphenylphosphino)butane (dppb) / tetrahydrofuran / 6 h / 60 °C

With potassium hydroxide; 1,4-di(diphenylphosphino)-butane; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; dimethyl sulfoxide;
DOI:10.1021/jo00269a026