2,2-bis(benzyloxymethyl)-1,3-bis(3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranosyl-oxy)-propane butane 1N,4N'-dioyl amide

Base Information

• Chemical Name: 2,2-bis(benzyloxymethyl)-1,3-bis(3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranosyl-oxy)-propane butane 1N,4N'-dioyl amide
• CAS No.: 592529-48-1
• Molecular Formula: C₄₇H₆₀N₂O₂₀
• Molecular Weight: 972.995
• Mol file: 592529-48-1.mol

Synonyms:2,2-bis(benzyloxymethyl)-1,3-bis(3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranosyl-oxy)-propane butane 1N,4N'-dioyl amide

Chemical Property of 2,2-bis(benzyloxymethyl)-1,3-bis(3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranosyl-oxy)-propane butane 1N,4N'-dioyl amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-bis(benzyloxymethyl)-1,3-bis(3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranosyl-oxy)-propane butane 1N,4N'-dioyl amide

There total 1 articles about 2,2-bis(benzyloxymethyl)-1,3-bis(3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranosyl-oxy)-propane butane 1N,4N'-dioyl amide 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: 42.0%

methanol (67-56-1) + succinoyl dichloride (543-20-4) + 2,2-bis(benzyloxymethyl)-1,3-bis(3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranosyl-oxy)-propane → 2,2-bis(benzyloxymethyl)-1,3-bis(3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranosyl-oxy)-propane butane 1N,4N'-dioyl amide (592529-48-1) + 2,2-bis(benzyloxymethyl)-1-[3,4,6-tri-O-acetyl-2-deoxy-2-(3-methyloxycarbonyl-propanamido)-β-D-glucopyranosyl-oxy]-3-[3,4,6-tri-O-acetyl-2-deoxy-2-(3-carboxyl-propanamido)-β-D-glucopyranosyloxy]-propane + 2,2-bis(benzyloxymethyl)-1,3-bis[3,4,6-tri-O-acetyl-2-deoxy-2-(3-methyloxycarbonyl-propanamido)-β-D-glucopyranosyl-oxy]-propane

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 13h;

DOI:10.1016/S0008-6215(03)00129-0

Reference yield: 92.0%

2,2-bis(benzyloxymethyl)-1,3-bis(3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranosyl-oxy)-propane butane 1N,4N'-dioyl amide (592529-48-1) → 2,2-bis(benzyloxymethyl)-1,3-bis(2-amino-2-deoxy-β-D-glucopyranosyl-oxy)-propane butane 1N,4N'-dioyl amide (592529-54-9)

Guidance literature:

With water; triethylamine; In methanol; at 20 ℃; for 24h;

DOI:10.1016/S0008-6215(03)00129-0

Reference yield:

2,2-bis(benzyloxymethyl)-1,3-bis(3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranosyl-oxy)-propane butane 1N,4N'-dioyl amide (592529-48-1) → 2,2-bis-benzyloxymethyl-1-(O-2-acetamido-2-deoxy-β-D-glucopyranosyl-oxy)-3-[O-β-D-galactopyranosyl-(1->4)-(2-amino-2-deoxy-β-D-glucopyranosyl-oxy)]-propane butane-1N,4N'-dioyl amide

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / water; triethylamine / methanol / 24 h / 20 °C

2: 20 percent / bovine milk D-GlcNAc β-(1->4)-galactosyltransferase; UDP-glucose-4-epimerase; sodium cacodylate / MnCl2 / H2O / 96 h / 37 °C / pH 7.4 / Enzymatic reaction

With bovine milk D-GlcNAc β-(1->4)-galactosyltransferase; UDP-glucose-4-epimerase; water; sodium cacodylate; triethylamine; manganese(ll) chloride; In methanol; water;

DOI:10.1016/S0008-6215(03)00129-0

upstream raw materials:

methanol

succinoyl dichloride

Downstream raw materials:

2,2-bis(benzyloxymethyl)-1,3-bis(2-amino-2-deoxy-β-D-glucopyranosyl-oxy)-propane butane 1N,4N'-dioyl amide

2,2-bis(benzyloxymethyl)-1,3-bis[O-β-D-galactopyranosyl-(1->4)-(2-amino-2-deoxy-β-D-glucopyranosyl-oxy)]-propane butane 1N,4N'-dioyl amide

2,2-bis(benzyloxymethyl)-1,3-bis-[O-β-D-galactopyranosyl-(1->4)-(2-amino-2-deoxy-3-O-α-L-fucopyranosyl-β-D-glucopyranosyloxy)]-propane butane 1N,4N'-dioyl amide