p-tolyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: p-tolyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• CAS No.: 905266-84-4
• Molecular Formula: C₃₄H₃₉NO₆SSi
• Molecular Weight: 617.838
• Mol file: 905266-84-4.mol

Synonyms:p-tolyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property of p-tolyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-tolyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

There total 1 articles about p-tolyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-2-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: 85.0%

t-butyldimethylsiyl triflate (69739-34-0) + 4-methylphenyl 4,6-O-benzylidene-2-deoxyl-1-thio-2-phthalimido-β-D-glucopyranoside (220645-16-9) → p-tolyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (905266-84-4)

Guidance literature:

With 2,6-dimethylpyridine; 4 A molecular sieve; In dichloromethane; at 0 ℃; for 4h;

DOI:10.1016/j.carres.2006.01.007

Reference yield: 74.0%

p-tolyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (905266-84-4) + p-tolyl 3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside (807361-23-5) → p-tolyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Guidance literature:

p-tolyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside; With p-methylbenzenesulfenyl chloride; 4 A molecular sieve; silver trifluoromethanesulfonate; In diethyl ether; at -70 ℃; for 0.25h;

p-tolyl 3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside; In diethyl ether; at -10 ℃; for 2h;

DOI:10.1016/j.carres.2006.01.007

Reference yield: 45.0%

p-tolyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (905266-84-4) + 2-[(2S,3R,4R,5S,6R)-6-Benzyloxymethyl-5-hydroxy-4-(4-methoxy-benzyloxy)-2-p-tolylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione + methyl 3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside (97242-79-0) + p-tolyl 3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside (807361-23-5) → C55H56N2O12Si + C84H83N3O19Si + C84H85N3O20Si + C113H112N4O26Si

Guidance literature:

p-tolyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside; p-tolyl 3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside; With p-methylbenzenesulfenyl chloride; 4 A molecular sieve; silver trifluoromethanesulfonate; TTBP; In diethyl ether; at -70 - -20 ℃; for 2h;

2-[(2S,3R,4R,5S,6R)-6-Benzyloxymethyl-5-hydroxy-4-(4-methoxy-benzyloxy)-2-p-tolylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione; With 4 A molecular sieve; silver trifluoromethanesulfonate; In diethyl ether; at -20 ℃; for 1.83333h;

methyl 3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside; With p-methylbenzenesulfenyl chloride; 4 A molecular sieve; In diethyl ether; at -70 - -20 ℃; for 1.58333h;

DOI:10.1016/j.carres.2006.01.007

upstream raw materials:

t-butyldimethylsiyl triflate

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

Downstream raw materials:

p-tolyl 2-deoxy-2-N-phthalimido-3-O-tert-butyldimethylsilyl-4-O-benzyl-1-thio-β-D-glucopyranoside

p-tolyl 4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside