p-tolyl 6-O-benzyl-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: p-tolyl 6-O-benzyl-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside
• CAS No.: 959862-94-3
• Molecular Formula: C₂₈H₂₇NO₆S
• Molecular Weight: 505.591
• Mol file: 959862-94-3.mol

Synonyms:p-tolyl 6-O-benzyl-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property of p-tolyl 6-O-benzyl-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-tolyl 6-O-benzyl-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside

There total 2 articles about p-tolyl 6-O-benzyl-2-deoxy-2-N-phthalimido-1-thio-β-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: 82.0%

4-methylphenyl 4,6-O-benzylidene-2-deoxyl-1-thio-2-phthalimido-β-D-glucopyranoside (220645-16-9) → p-tolyl 6-O-benzyl-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside (959862-94-3)

Guidance literature:

With aluminum (III) chloride; trimethylamine-borane; In tetrahydrofuran; at 0 - 20 ℃; for 3h; regioselective reaction; Inert atmosphere;

DOI:10.1002/open.201300024

Reference yield: 73.0%

p-tolyl 4,6-O-benzylidene-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside → p-tolyl 6-O-benzyl-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside (959862-94-3)

Guidance literature:

p-tolyl 4,6-O-benzylidene-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside; With molecular sieve; sodium cyanoborohydride; In tetrahydrofuran; at 0 ℃; for 1h;

With hydrogenchloride; In tetrahydrofuran; diethyl ether; for 0.416667h; Further stages.;

DOI:10.1021/jo701694k

Reference yield: 93.0%

p-tolyl 6-O-benzyl-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside (959862-94-3) + p-tolyl 3-O-allyl-4,6-O-benzylidene-2-O-levulinoyl-1-thio-β-D-galactopyranoside → p-tolyl (3-O-allyl-4,6-O-benzylidene-2-O-levulinoyl-β-D-galactopyranosyl)-(1→4)-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Guidance literature:

p-tolyl 3-O-allyl-4,6-O-benzylidene-2-O-levulinoyl-1-thio-β-D-galactopyranoside; With silver trifluoromethanesulfonate; In dichloromethane; acetonitrile; at -78 ℃; for 0.25h; Molecular sieve;

With p-methylbenzenesulfenyl chloride; In dichloromethane; acetonitrile; at -78 ℃; Molecular sieve;

p-tolyl 6-O-benzyl-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside; With 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; acetonitrile; at -78 ℃; for 1h; stereoselective reaction; Molecular sieve;

DOI:10.1021/acs.orglett.7b03275

upstream raw materials:

4-methylphenyl 4,6-O-benzylidene-2-deoxyl-1-thio-2-phthalimido-β-D-glucopyranoside

Downstream raw materials:

p-tolyl (methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trichloroacetamido-D-glycero-α-D-galacto-2-nonulopyranosylonate-(2->3))-2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyl-(1->4)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

3-oxobutyl 6-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside

p-tolyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-6-O-benzyl-2-deoxy-2-phthalimido-1-thiol-β-D-glucopyranoside