ethyl 2,3,6-trideoxy-4-O-p-methoxybenzyl-6-C-(4'-vinyloxyazetidin-2'-on-1'-yl)-α-D-erythro-hexopyranoside

Base Information

Chemical Name:ethyl 2,3,6-trideoxy-4-O-p-methoxybenzyl-6-C-(4'-vinyloxyazetidin-2'-on-1'-yl)-α-D-erythro-hexopyranoside
CAS No.:495379-07-2
Molecular Formula:C₂₁H₂₉NO₆
Molecular Weight:391.464
Hs Code.:

Synonyms:ethyl 2,3,6-trideoxy-4-O-p-methoxybenzyl-6-C-(4'-vinyloxyazetidin-2'-on-1'-yl)-α-D-erythro-hexopyranoside

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Chemical Property of ethyl 2,3,6-trideoxy-4-O-p-methoxybenzyl-6-C-(4'-vinyloxyazetidin-2'-on-1'-yl)-α-D-erythro-hexopyranoside

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Technology Process of ethyl 2,3,6-trideoxy-4-O-p-methoxybenzyl-6-C-(4'-vinyloxyazetidin-2'-on-1'-yl)-α-D-erythro-hexopyranoside

There total 5 articles about ethyl 2,3,6-trideoxy-4-O-p-methoxybenzyl-6-C-(4'-vinyloxyazetidin-2'-on-1'-yl)-α-D-erythro-hexopyranoside 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: 52.0%

: 4-vinyloxyazetidin-2-one

: ethyl 2,3-dideoxy-4-O-p-methoxybenzyl-6-O-triflyl-α-D-erythro-hexopyranoside

: 495379-07-2
ethyl 2,3,6-trideoxy-4-O-p-methoxybenzyl-6-C-(4'-vinyloxyazetidin-2'-on-1'-yl)-α-D-erythro-hexopyranoside

Guidance literature:: With n-butyllithium; tetra(n-butyl)ammonium hydrogensulfate; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h;
DOI:10.1016/S0008-6215(02)00139-8

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 495379-07-2
ethyl 2,3,6-trideoxy-4-O-p-methoxybenzyl-6-C-(4'-vinyloxyazetidin-2'-on-1'-yl)-α-D-erythro-hexopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 70 percent / KOH; Bu₄NBr / toluene / 2.33 h

2: 83 percent / TBAF / tetrahydrofuran / 20 h

3: 2,6-lutidine / CH₂Cl₂ / 0.17 h / -20 °C

4: 52 percent / Bu₄NHSO₄; BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

With 2,6-dimethylpyridine; potassium hydroxide; n-butyllithium; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; tetra(n-butyl)ammonium hydrogensulfate; In tetrahydrofuran; hexane; dichloromethane; toluene;
DOI:10.1016/S0008-6215(02)00139-8

Reference yield:

: 495379-00-5
ethyl 2,3-dideoxy-4-O-p-methoxybenzyl-α-D-erythro-hexopyranoside

: 495379-07-2
ethyl 2,3,6-trideoxy-4-O-p-methoxybenzyl-6-C-(4'-vinyloxyazetidin-2'-on-1'-yl)-α-D-erythro-hexopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 2,6-lutidine / CH₂Cl₂ / 0.17 h / -20 °C

2: 52 percent / Bu₄NHSO₄; BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

With 2,6-dimethylpyridine; n-butyllithium; tetra(n-butyl)ammonium hydrogensulfate; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1016/S0008-6215(02)00139-8