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

Base Information

• Chemical Name: 3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-1,2-O-isopropylidene-sn-glycerol
• CAS No.: 1192755-03-5
• Molecular Formula: C₃₃H₃₉N₃O₇
• Molecular Weight: 589.689
• Mol file: 1192755-03-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 20 articles about 3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-1,2-O-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: 88.0%

6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosyl trichloroacetimidate (1383449-98-6) + (S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol (22323-82-6,36543-79-0) → 3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-1,2-O-isopropylidene-sn-glycerol (1192755-03-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In diethyl ether; at 0 ℃; for 0.5h; optical yield given as %de; Inert atmosphere; Molecular sieve;

DOI:10.1016/j.carres.2012.04.005

Reference yield: 46.0%

(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-β-D-glucosyl)-N,2,2-tri-(p-chlorophenyl)ethanimidoate + (S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol (22323-82-6,36543-79-0) → 3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-1,2-O-isopropylidene-sn-glycerol (1192755-03-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.carres.2009.05.022

Reference yield:

(S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol (22323-82-6,36543-79-0) + p-tolyl 6-azido-2,3,4-tri-O-benzyl-6-deoxy-1-thio-β-D-glucopyranoside → 3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-1,2-O-isopropylidene-sn-glycerol (1192755-03-5) + 3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-β-D-glucopyranosyl)-1,2-O-isopropylidene-sn-glycerol (1383450-02-9)

Guidance literature:

p-tolyl 6-azido-2,3,4-tri-O-benzyl-6-deoxy-1-thio-β-D-glucopyranoside; With N-iodo-succinimide; In diethyl ether; at 20 ℃; for 0.166667h; Inert atmosphere; Molecular sieve;

(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 72h; optical yield given as %de; Inert atmosphere; Molecular sieve;

DOI:10.1016/j.carres.2012.04.005

upstream raw materials:

(S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol

6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosyl trichloroacetimidate

p-tolyl 2,3,4-tri-O-benzyl-6-O-p-tosyl-1-thio-β-D-glucopyranoside

((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-p-tolylsulfanyl-tetrahydro-pyran-2-yl)-methanol

Downstream raw materials:

3-O-(6'-azido-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-sn-glycerol

1,2-di-O-palmitoyl-3-O-(N-palmitoyl-6'-amino-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-sn-glycerol

1,2-di-O-octanoyl-3-O-(N-octanoyl-6'-amino-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-sn-glycerol

1,2-di-O-hydrocinnamoyl-3-O-(N-hydrocinnamoyl-6'-amino-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucopyranosyl)-sn-glycerol