5-azidopentyl (2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Base Information

• Chemical Name: 5-azidopentyl (2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS No.: 190269-49-9
• Molecular Formula: C₅₆H₆₂N₄O₁₂
• Molecular Weight: 983.128
• Mol file: 190269-49-9.mol

Synonyms:5-azidopentyl (2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Chemical Property of 5-azidopentyl (2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-azidopentyl (2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

There total 12 articles about 5-azidopentyl (2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-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: 92.0%

C42H50N4O12 (1262971-58-3) + benzyl bromide (100-39-0) → 5-azidopentyl (2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (190269-49-9)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; for 6h;

DOI:10.1021/ja104657b

Reference yield: 84.0%

5-azido-1-pentanol (170220-11-8) + ethyl (2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (177358-21-3) → 5-azidopentyl (2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (190269-49-9)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; 3 A molecular sieve; In dichloromethane;

DOI:10.1016/S0008-6215(97)00013-X

Reference yield:

1 ,5-pentanediol (111-29-5) → 5-azidopentyl (2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (190269-49-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 45 percent / 2,4,6-collidine / CH₂Cl₂ / 4 h / -20 °C

2: 95 percent / PPh₃, HN₃, DEAD / tetrahydrofuran / 1.5 h / Ambient temperature

3: 97 percent / NaOMe / methanol / 48 h

4: 84 percent / 3A molecular sieves, NIS, TfOH / CH₂Cl₂

With 2,4,6-trimethyl-pyridine; N-iodo-succinimide; tris-(2-chloro-ethyl)-amine; trifluorormethanesulfonic acid; 3 A molecular sieve; sodium methylate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/S0008-6215(97)00013-X

upstream raw materials:

5-azido-1-pentanol

ethyl (2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

1 ,5-pentanediol

1-benzoyloxypentan-5-ol

Downstream raw materials:

5-azidopentyl (2,6-di-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside