8-phenylmethyloxy-3,6-dioxaoctyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: 8-phenylmethyloxy-3,6-dioxaoctyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranoside
• CAS No.: 1391835-76-9
• Molecular Formula: C₃₉H₅₅NO₂₀
• Molecular Weight: 857.86
• Mol file: 1391835-76-9.mol

Synonyms:8-phenylmethyloxy-3,6-dioxaoctyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranoside

Chemical Property of 8-phenylmethyloxy-3,6-dioxaoctyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-phenylmethyloxy-3,6-dioxaoctyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranoside

There total 5 articles about 8-phenylmethyloxy-3,6-dioxaoctyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-acetyl-2-acetamido-2-deoxy-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: 56.2%

triethylene glycol monobenzyl ether (55489-58-2,1201808-31-2) + acetic anhydride (108-24-7) + 3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-2-iodo-α-D-manno-pyranosyl azide (188426-25-7) → 8-phenylmethyloxy-3,6-dioxaoctyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranoside (1391835-76-9)

Guidance literature:

triethylene glycol monobenzyl ether; 3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-2-iodo-α-D-manno-pyranosyl azide; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere; Molecular sieve;

With triphenylphosphine; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

acetic anhydride; stereoselective reaction; Further stages;

DOI:10.1016/j.tet.2012.06.035

Reference yield:

hexa-O-acetyl-D-lactal (51450-24-9) → 8-phenylmethyloxy-3,6-dioxaoctyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranoside (1391835-76-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium azide; Iodine monochloride / acetonitrile / 0.5 h / 0 °C

2.1: dichloromethane / 0.5 h / 0 °C / Inert atmosphere; Molecular sieve

2.2: 0 - 20 °C / Inert atmosphere

With sodium azide; Iodine monochloride; In dichloromethane; acetonitrile;

DOI:10.1016/j.tet.2012.06.035

Reference yield:

benzyl bromide (100-39-0) → 8-phenylmethyloxy-3,6-dioxaoctyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranoside (1391835-76-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: silver(l) oxide / dichloromethane / 2 h / Inert atmosphere

2.1: dichloromethane / 0.5 h / 0 °C / Inert atmosphere; Molecular sieve

2.2: 0 - 20 °C / Inert atmosphere

With silver(l) oxide; In dichloromethane;

DOI:10.1016/j.tet.2012.06.035

upstream raw materials:

hexa-O-acetyl-D-lactal

triethylene glycol monobenzyl ether

acetic anhydride

3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-2-iodo-α-D-manno-pyranosyl azide