3,6-di-O-benzyl-4-O-(chloroacetyl)-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-3-O-benzyl-2-deoxy-6-O-(p-methoxyphenyl)-2-phthalimido-β-D-glucopyranosyl azide

Base Information

• Chemical Name: 3,6-di-O-benzyl-4-O-(chloroacetyl)-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-3-O-benzyl-2-deoxy-6-O-(p-methoxyphenyl)-2-phthalimido-β-D-glucopyranosyl azide
• CAS No.: 182923-95-1
• Molecular Formula: C₅₈H₅₂ClN₅O₁₄
• Molecular Weight: 1078.53
• Mol file: 182923-95-1.mol

Synonyms:

Chemical Property of 3,6-di-O-benzyl-4-O-(chloroacetyl)-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-3-O-benzyl-2-deoxy-6-O-(p-methoxyphenyl)-2-phthalimido-β-D-glucopyranosyl azide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,6-di-O-benzyl-4-O-(chloroacetyl)-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-3-O-benzyl-2-deoxy-6-O-(p-methoxyphenyl)-2-phthalimido-β-D-glucopyranosyl azide

There total 15 articles about 3,6-di-O-benzyl-4-O-(chloroacetyl)-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-3-O-benzyl-2-deoxy-6-O-(p-methoxyphenyl)-2-phthalimido-β-D-glucopyranosyl azide 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:

ethyl 3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (560129-48-8) + 3-O-benzyl-2-deoxy-6-O-(p-methoxyphenyl)-2-phthalimido-β-D-glucopyranosyl azide (182923-92-8) → 3,6-di-O-benzyl-4-O-(chloroacetyl)-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-3-O-benzyl-2-deoxy-6-O-(p-methoxyphenyl)-2-phthalimido-β-D-glucopyranosyl azide (182923-95-1)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at -35 - -30 ℃; for 0.5h; Molecular sieve;

DOI:10.1002/ejoc.201200468

Reference yield:

3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride (182923-79-1) + 3-O-benzyl-2-deoxy-6-O-(p-methoxyphenyl)-2-phthalimido-β-D-glucopyranosyl azide (182923-92-8) → 3,6-di-O-benzyl-4-O-(chloroacetyl)-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-3-O-benzyl-2-deoxy-6-O-(p-methoxyphenyl)-2-phthalimido-β-D-glucopyranosyl azide (182923-95-1)

Guidance literature:

With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1016/0040-4039(96)01394-9

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) → 3,6-di-O-benzyl-4-O-(chloroacetyl)-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-3-O-benzyl-2-deoxy-6-O-(p-methoxyphenyl)-2-phthalimido-β-D-glucopyranosyl azide (182923-95-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / Na(CN)BH₃, mol. sieves 4 Angstroem / tetrahydrofuran / 0 °C

2: 95 percent / pyridine / CH₂Cl₂ / 0 °C

3: 91 percent / HF-pyridine, NBS / CH₂Cl₂ / 0 °C

4: BF₃*Et₂O, mol. sieves 4 Angstroem / CH₂Cl₂

With pyridine; N-Bromosuccinimide; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium cyanoborohydride; pyridine hydrogenfluoride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0040-4039(96)01394-9

upstream raw materials:

3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride

3-O-benzyl-2-deoxy-6-O-(p-methoxyphenyl)-2-phthalimido-β-D-glucopyranosyl azide

4-methoxy-phenol

ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Downstream raw materials:

3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-3-O-benzyl-2-deoxy-6-O-(p-methoxyphenyl)-2-phthalimido-β-D-glucopyranosyl azide