ethyl 2,3-dideoxy-4-O-(3'R,4'S)-(3'-methylazetidin-2'-on-4'-yl)-6-O-tosyl-α-D-erythro-hexopyranoside

Base Information

Chemical Name:ethyl 2,3-dideoxy-4-O-(3'R,4'S)-(3'-methylazetidin-2'-on-4'-yl)-6-O-tosyl-α-D-erythro-hexopyranoside
CAS No.:495379-11-8
Molecular Formula:C₁₉H₂₇NO₇S
Molecular Weight:413.492
Hs Code.:

Synonyms:ethyl 2,3-dideoxy-4-O-(3'R,4'S)-(3'-methylazetidin-2'-on-4'-yl)-6-O-tosyl-α-D-erythro-hexopyranoside

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Chemical Property of ethyl 2,3-dideoxy-4-O-(3'R,4'S)-(3'-methylazetidin-2'-on-4'-yl)-6-O-tosyl-α-D-erythro-hexopyranoside

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Technology Process of ethyl 2,3-dideoxy-4-O-(3'R,4'S)-(3'-methylazetidin-2'-on-4'-yl)-6-O-tosyl-α-D-erythro-hexopyranoside

There total 9 articles about ethyl 2,3-dideoxy-4-O-(3'R,4'S)-(3'-methylazetidin-2'-on-4'-yl)-6-O-tosyl-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: 75.0%

: 98-59-9
p-toluenesulfonyl chloride

: 495379-10-7
ethyl 2,3-dideoxy-4-O-(3'R,4'S)-(3'-methylazetidin-2'-on-4'-yl)-α-D-erythro-hexopyranoside

: 495379-11-8
ethyl 2,3-dideoxy-4-O-(3'R,4'S)-(3'-methylazetidin-2'-on-4'-yl)-6-O-tosyl-α-D-erythro-hexopyranoside

Guidance literature:: With pyridine; at 20 ℃; for 20h;
DOI:10.1016/S0008-6215(02)00139-8

Reference yield:

: 1189-71-5
isocyanate de chlorosulfonyle

: 495379-05-0
ethyl 2,3-dideoxy-6-O-tosyl-(Z)-4-O-propenyl-α-D-erythro-hexopyranoside

: 495379-11-8
ethyl 2,3-dideoxy-4-O-(3'R,4'S)-(3'-methylazetidin-2'-on-4'-yl)-6-O-tosyl-α-D-erythro-hexopyranoside

: ethyl 2,3-dideoxy-4-O-(3'S,4'R)-(3'-methylazetidin-2'-on-4'-yl)-6-O-tosyl-α-D-erythro-hexopyranoside

Guidance literature:: isocyanate de chlorosulfonyle; ethyl 2,3-dideoxy-6-O-tosyl-(Z)-4-O-propenyl-α-D-erythro-hexopyranoside; With sodium carbonate; In toluene; at -78 ℃;

With [(CH₃OC₂H₄O)2AlH₂]Na; In toluene; at -78 ℃; Title compound not separated from byproducts;
DOI:10.1016/S0008-6215(02)00139-8

Reference yield:

: 495378-93-3
ethyl 2,3-dideoxy-6-O-trityl-α-D-erythro-hexopyranoside

: 495379-11-8
ethyl 2,3-dideoxy-4-O-(3'R,4'S)-(3'-methylazetidin-2'-on-4'-yl)-6-O-tosyl-α-D-erythro-hexopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 72 percent / KOH; Bu₄NBr / toluene / 2 h

2.1: 86 percent / t-BuOK / dimethylsulfoxide / 1.5 h / 50 °C

3.1: Na₂CO₃ / toluene / 1.5 h / -78 °C

3.2: 54 percent / [(CH₃OC₂H₄O)2AlH₂]Na / toluene / 0.5 h / -78 °C

4.1: NH₃; Na / tetrahydrofuran / 0.42 h / -70 °C

5.1: 75 percent / pyridine / 20 h / 20 °C

With pyridine; potassium hydroxide; potassium tert-butylate; tetrabutylammomium bromide; ammonia; sodium; sodium carbonate; In tetrahydrofuran; dimethyl sulfoxide; toluene;
DOI:10.1016/S0008-6215(02)00139-8