isopropyl 3,4,6-tri-O-benzyl-α-D-glucopyranoside

Base Information

• Chemical Name: isopropyl 3,4,6-tri-O-benzyl-α-D-glucopyranoside
• CAS No.: 170428-27-0
• Molecular Formula: C₃₀H₃₆O₆
• Molecular Weight: 492.612
• Mol file: 170428-27-0.mol

Synonyms:isopropyl 3,4,6-tri-O-benzyl-α-D-glucopyranoside

Chemical Property of isopropyl 3,4,6-tri-O-benzyl-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of isopropyl 3,4,6-tri-O-benzyl-α-D-glucopyranoside

There total 8 articles about isopropyl 3,4,6-tri-O-benzyl-α-D-glucopyranoside 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: 77.0%

2-methoxy-2-(S)-phenyl-(3,4,6-tri-O-benzyl-1,2-dideoxy-β-D-glucopyranoso)[1,2-e]-1,4-oxathiane (R)-S-oxide (1197820-03-3) + isopropyl alcohol (67-63-0,8013-70-5) → isopropyl 3,4,6-tri-O-benzyl-α-D-glucopyranoside (170428-27-0)

Guidance literature:

2-methoxy-2-(S)-phenyl-(3,4,6-tri-O-benzyl-1,2-dideoxy-β-D-glucopyranoso)[1,2-e]-1,4-oxathiane (R)-S-oxide; With 1,2,3-trimethoxybenzene; trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; at -30 - -10 ℃; 4 ? molecular sieves; Inert atmosphere;

isopropyl alcohol; With N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; at -10 - 50 ℃; Inert atmosphere;

With methanol; boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1039/b913308a

Reference yield: 57.0%

C33H38O7S (1359734-73-8) + isopropyl alcohol (67-63-0,8013-70-5) → isopropyl 3,4,6-tri-O-benzyl-α-D-glucopyranoside (170428-27-0)

Guidance literature:

C₃₃H₃₈O₇S; With 1,2,3-trimethoxybenzene; trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -30 - 20 ℃; for 0.166667h; Inert atmosphere; Molecular sieve;

isopropyl alcohol; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 24h; Inert atmosphere;

With boron trifluoride diethyl etherate; In methanol; dichloromethane; at 20 ℃; for 0.5h; optical yield given as %de; Inert atmosphere;

DOI:10.1016/j.carres.2011.07.020

Reference yield: 44.0%

chlorotitanium(IV) triisopropoxide + 3,4,6-tri-O-benzyl-D-glucal epoxide (74372-90-0) + methyl-2,3,4-tri-O-benzyl-6,7-dideoxy-6,6,7,7-tetradehydro-α-D-glucoheptopyranoside (161663-92-9) → methyl 7-deoxy-2,3,4-tri-O-benzyl-7-(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-α-D-gluco-hept-6-ynopyranoside (195724-14-2) + isopropyl 3,4,6-tri-O-benzyl-α-D-glucopyranoside (170428-27-0)

Guidance literature:

methyl-2,3,4-tri-O-benzyl-6,7-dideoxy-6,6,7,7-tetradehydro-α-D-glucoheptopyranoside; With n-butyllithium; In tetrahydrofuran; hexane; at -50 ℃; for 0.333333h;

chlorotitanium(IV) triisopropoxide; In tetrahydrofuran; hexane; at -50 ℃; for 0.25h;

3,4,6-tri-O-benzyl-D-glucal epoxide; In tetrahydrofuran; hexane; at -50 - -20 ℃;

DOI:10.1081/CAR-120026458

upstream raw materials:

3-(tetrahydropyran-2'-yloxy)propyne

3,4,6-tri-O-benzyl-D-glucal epoxide

methyl-2,3,4-tri-O-benzyl-6,7-dideoxy-6,6,7,7-tetradehydro-α-D-glucoheptopyranoside

trimethylsilylacetylene

Downstream raw materials:

isopropyl-α-D-glucopyranoside

Refernces

• 1、 Padungros, Panuwat,Alberch, Laura,Wei, Alexander. "Glycosyl dithiocarbamates: β-selective couplings without auxiliary groups". . p. 2611 - 2624. Retrieved 2014/04/17.
• 2、 Fascione, Martin A.,Adshead, Sophie J.,Stalford, Susanne A.,Kilner, Colin A.,Leach, Andrew G.,Turnbull, W. Bruce. "Stereoselective glycosylation using oxathiane glycosyl donors". supporting information; experimental part. p. 5841 - 5843. Retrieved 2010/01/31.