p-tolyl 2-O-(2,2-dimethyl-4 azidobutanoyl)-3-O-(4-oxopentanoyl)-4-O-benzyl-1-thio-α-L-rhamnopyranoside

Base Information

Chemical Name:p-tolyl 2-O-(2,2-dimethyl-4 azidobutanoyl)-3-O-(4-oxopentanoyl)-4-O-benzyl-1-thio-α-L-rhamnopyranoside
CAS No.:1431139-44-4
Molecular Formula:C₃₁H₃₉N₃O₇S
Molecular Weight:597.733
Hs Code.:

Synonyms:p-tolyl 2-O-(2,2-dimethyl-4 azidobutanoyl)-3-O-(4-oxopentanoyl)-4-O-benzyl-1-thio-α-L-rhamnopyranoside

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Chemical Property of p-tolyl 2-O-(2,2-dimethyl-4 azidobutanoyl)-3-O-(4-oxopentanoyl)-4-O-benzyl-1-thio-α-L-rhamnopyranoside

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Technology Process of p-tolyl 2-O-(2,2-dimethyl-4 azidobutanoyl)-3-O-(4-oxopentanoyl)-4-O-benzyl-1-thio-α-L-rhamnopyranoside

There total 3 articles about p-tolyl 2-O-(2,2-dimethyl-4 azidobutanoyl)-3-O-(4-oxopentanoyl)-4-O-benzyl-1-thio-α-L-rhamnopyranoside 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%

: 1431139-43-3
p-tolyl 2-O-(2,2-dimethyl-4-azidobutanoyl)-4-O-benzyl-1-thio-α-L-rhamnopyranoside

: 123-76-2
levulinic acid

: 1431139-44-4
p-tolyl 2-O-(2,2-dimethyl-4 azidobutanoyl)-3-O-(4-oxopentanoyl)-4-O-benzyl-1-thio-α-L-rhamnopyranoside

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃;
DOI:10.1021/ol4008475

Reference yield: 88.0%

: 2508-29-4
5-hydroxypentylamine

: 100-52-7
benzaldehyde

: 501-53-1,94274-21-2
benzyl chloroformate

: 1431139-44-4
p-tolyl 2-O-(2,2-dimethyl-4 azidobutanoyl)-3-O-(4-oxopentanoyl)-4-O-benzyl-1-thio-α-L-rhamnopyranoside

Guidance literature:: 5-hydroxypentylamine; benzaldehyde; In ethanol; at 20 - 50 ℃;

With sodium tetrahydroborate; In methanol; at 0 - 20 ℃;

benzyl chloroformate; With sodium hydrogencarbonate; In diethyl ether; water; at 0 - 20 ℃; for 14h;
DOI:10.1021/ol4008475

Reference yield:

: 1431139-42-2
p-tolyl 2-O-(2,2-dimethyl-4-azidobutanoyl)-3-O-p-methoxybenzyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

: 1431139-44-4
p-tolyl 2-O-(2,2-dimethyl-4 azidobutanoyl)-3-O-(4-oxopentanoyl)-4-O-benzyl-1-thio-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: para-thiocresol; trifluoroacetic acid / dichloromethane / 0 - 20 °C

2: dicyclohexyl-carbodiimide; dmap / dichloromethane / 20 °C

With dmap; para-thiocresol; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dichloromethane; 2: |Steglich Esterification;
DOI:10.1021/ol4008475