3-azido-1-O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)propanol

Base Information

• Chemical Name: 3-azido-1-O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)propanol
• CAS No.: 548477-86-7
• Molecular Formula: C₃₁H₃₂N₄O₇
• Molecular Weight: 572.618
• Mol file: 548477-86-7.mol

Synonyms:3-azido-1-O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)propanol

Chemical Property of 3-azido-1-O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)propanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-azido-1-O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)propanol

There total 3 articles about 3-azido-1-O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)propanol 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: 71.0%

3-azidopropyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (675856-93-6) → 3-azido-1-O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)propanol (548477-86-7)

Guidance literature:

With triethylsilane; trifluorormethanesulfonic acid; In dichloromethane; at -78 ℃; for 0.333333h;

DOI:10.1080/07328300500308113

Reference yield:

Ethyl 4,6-O-benzylidene-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside → 3-azido-1-O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)propanol (548477-86-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / 1-benzenesulfinylpiperidine; trifluoromethanesulfonic anhydride; tri-tert-butylpyrimidine / molecular sieves 3 Angstroem / CH₂Cl₂ / -60 - 0 °C

2: 71 percent / triethylsilane; trifluoromethanesulfonic acid / CH₂Cl₂ / 0.33 h / -78 °C

With triethylsilane; 1-benzenesulfinyl piperidine; trifluorormethanesulfonic acid; 2,4,5-tri-tert-butylpyrimidine; trifluoromethanesulfonic acid anhydride; 3 A molecular sieve; In dichloromethane;

DOI:10.1080/07328300500308113

Reference yield:

2-((6S,7R,8aS)-8-benzyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione (129519-27-3) → 3-azido-1-O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)propanol (548477-86-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 2,4,6-tri-tert-butylpyrimidine; Ph₂SO; trifluoromethanesulfonic anhydride / CH₂Cl₂ / 0.08 h / -60 °C

1.2: 84 percent / CH₂Cl₂ / -60 - -10 °C

2.1: 127 mg / triethylsilane; TfOH / CH₂Cl₂ / 0.33 h / -78 °C

With triethylsilane; trifluorormethanesulfonic acid; 1,1'-sulfinylbisbenzene; trifluoromethanesulfonic acid anhydride; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane;

DOI:10.1016/j.tet.2003.11.084

upstream raw materials:

3-azidopropyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

2-((6S,7R,8aS)-8-benzyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione