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

Base Information

• Chemical Name: p-tolyl 2-deoxy-2-N-phthalimido-3-O-tert-butyldimethylsilyl-4-O-benzyl-1-thio-β-D-glucopyranoside
• CAS No.: 909795-60-4
• Molecular Formula: C₃₄H₄₁NO₆SSi
• Molecular Weight: 619.854
• Mol file: 909795-60-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about p-tolyl 2-deoxy-2-N-phthalimido-3-O-tert-butyldimethylsilyl-4-O-benzyl-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: 77.0%

p-tolyl 2-deoxy-2-N-phthalimido-3-O-tert-butyldimethylsilyl-4,6-O-benzyl-1-thio-β-D-glucopyranoside → p-tolyl 2-deoxy-2-N-phthalimido-3-O-tert-butyldimethylsilyl-4-O-benzyl-1-thio-β-D-glucopyranoside (909795-60-4)

Guidance literature:

With di-n-butylboryl trifluoromethanesulfonate; borane; In tetrahydrofuran; at 0 ℃; for 3h;

DOI:10.1002/chem.200600290

Reference yield:

p-tolyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (905266-84-4) → p-tolyl 2-deoxy-2-N-phthalimido-3-O-tert-butyldimethylsilyl-4-O-benzyl-1-thio-β-D-glucopyranoside (909795-60-4)

Guidance literature:

With borane-THF; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 - 0 ℃; for 4h;

DOI:10.1016/j.carres.2006.01.007

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → p-tolyl 2-deoxy-2-N-phthalimido-3-O-tert-butyldimethylsilyl-4-O-benzyl-1-thio-β-D-glucopyranoside (909795-60-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / 4 Angstroem molecular sieves; 2,6 lutidine / CH₂Cl₂ / 4 h / 0 °C

2: 0.39 g / BH₃*THF; trimethylsiyl triflate / CH₂Cl₂ / 4 h / -20 - 0 °C

With 2,6-dimethylpyridine; borane-THF; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane;

DOI:10.1016/j.carres.2006.01.007

upstream raw materials:

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

t-butyldimethylsiyl triflate

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

Downstream raw materials:

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