3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-β-D-galactosyl)-1,2-isopropylidene-sn-glycerol

Base Information

Chemical Name:3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-β-D-galactosyl)-1,2-isopropylidene-sn-glycerol
CAS No.:1446098-78-7
Molecular Formula:C₃₃H₃₉N₃O₇
Molecular Weight:589.689
Hs Code.:

Synonyms:3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-β-D-galactosyl)-1,2-isopropylidene-sn-glycerol

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Chemical Property of 3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-β-D-galactosyl)-1,2-isopropylidene-sn-glycerol

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Technology Process of 3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-β-D-galactosyl)-1,2-isopropylidene-sn-glycerol

There total 14 articles about 3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-β-D-galactosyl)-1,2-isopropylidene-sn-glycerol 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:

: 22323-82-6,36543-79-0
(S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol

: p-tolyl-6-azido-2,3,4-tri-O-benzyl-6-deoxy-1-thio-β-D-galactopyranoside

: 1446098-77-6
3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-galactosyl)-1,2-isopropylidene-sn-glycerol

: 1446098-78-7
3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-β-D-galactosyl)-1,2-isopropylidene-sn-glycerol

Guidance literature:: p-tolyl-6-azido-2,3,4-tri-O-benzyl-6-deoxy-1-thio-β-D-galactopyranoside; With N-iodo-succinimide; In diethyl ether; at 0 ℃; for 0.166667h; Molecular sieve; Inert atmosphere;

(S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol; With 2,6-di-tert-butyl-4-methylpyridine; trimethylsilyl trifluoromethanesulfonate; In diethyl ether; at 20 ℃; for 5h; Overall yield = 83 %; Overall yield = 115 mg; Inert atmosphere; Molecular sieve;
DOI:10.1016/j.carres.2013.02.008

Reference yield:

: O-(6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-galactosyl)trichloroacetimidate

: 22323-82-6,36543-79-0
(S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol

: 1446098-77-6
3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-galactosyl)-1,2-isopropylidene-sn-glycerol

: 1446098-78-7
3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-β-D-galactosyl)-1,2-isopropylidene-sn-glycerol

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In diethyl ether; at 0 ℃; for 0.5h; Overall yield = 86 %; Overall yield = 43.6 mg; Molecular sieve;
DOI:10.1016/j.carres.2013.02.008

Reference yield:

: (2S,3R,4S,5R,6R)-2-p-Tolylsulfanyl-6-trityloxymethyl-tetrahydro-pyran-3,4,5-triol

: 1446098-78-7
3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-β-D-galactosyl)-1,2-isopropylidene-sn-glycerol

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 6 h / 0 - 20 °C

2.1: acetic acid / ethanol / 16 h / 90 °C

3.1: dmap; triethylamine / dichloromethane / 5 h / 20 °C

4.1: sodium azide / N,N-dimethyl-formamide / 65 °C

5.1: N-iodo-succinimide / diethyl ether / 0.17 h / 0 °C / Molecular sieve; Inert atmosphere

5.2: 5 h / 20 °C / Inert atmosphere; Molecular sieve

With dmap; N-iodo-succinimide; sodium azide; sodium hydride; acetic acid; triethylamine; In diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.carres.2013.02.008