benzyl 6-O-[4-O-acetyl-3-O-(4-methoxybenzyl)-2-O-methyl-α-L-fucopyranosyl]-4-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Base Information

• Chemical Name: benzyl 6-O-[4-O-acetyl-3-O-(4-methoxybenzyl)-2-O-methyl-α-L-fucopyranosyl]-4-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS No.: 207917-29-1
• Molecular Formula: C₇₂H₇₆N₄O₁₇
• Molecular Weight: 1269.41
• Mol file: 207917-29-1.mol

Synonyms:benzyl 6-O-[4-O-acetyl-3-O-(4-methoxybenzyl)-2-O-methyl-α-L-fucopyranosyl]-4-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Chemical Property of benzyl 6-O-[4-O-acetyl-3-O-(4-methoxybenzyl)-2-O-methyl-α-L-fucopyranosyl]-4-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3-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 benzyl 6-O-[4-O-acetyl-3-O-(4-methoxybenzyl)-2-O-methyl-α-L-fucopyranosyl]-4-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

There total 11 articles about benzyl 6-O-[4-O-acetyl-3-O-(4-methoxybenzyl)-2-O-methyl-α-L-fucopyranosyl]-4-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3-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: 73.0%

ethyl 4-O-acetyl-3-O-(p-methoxybenzyl)-2-O-methyl-1-thio-β-L-fucopyranoside (146399-63-5) + benzyl 4-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (207917-28-0) → benzyl 6-O-[4-O-acetyl-3-O-(4-methoxybenzyl)-2-O-methyl-α-L-fucopyranosyl]-4-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (207917-29-1)

Guidance literature:

With 4 Angstroem MS; tetrabutylammomium bromide; copper(ll) bromide; In dichloromethane; at 20 ℃; for 72h;

DOI:10.1007/bf02495661

Reference yield:

6-deoxy-L-galactose (73-34-7,87-96-7,488-79-9,551-63-3,609-01-8,643-17-4,643-18-5,4164-09-4,6014-42-2,6155-36-8,6189-71-5,6696-41-9,6736-43-2,13224-93-6,22611-09-2,28161-49-1,28161-50-4,28161-52-6,45864-36-6,63814-64-2,71116-59-1,71116-61-5,72598-05-1,87936-88-7,87936-89-8,97466-79-0,116908-82-8,120442-60-6,123484-22-0,133576-32-6) → benzyl 6-O-[4-O-acetyl-3-O-(4-methoxybenzyl)-2-O-methyl-α-L-fucopyranosyl]-4-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (207917-29-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) Ac₂O, AcONa, 2.) Et₂O*BF₃, 3.) MeONa / 1.) 100 deg C, 2.) CH₂Cl₂, 8 h, 3.) MeOH, 20 deg C, 16 h

2: TsOH*H₂O / 24 h / 20 °C

3: KOH / dimethylsulfoxide / 0.5 h / 30 - 40 °C

4: 90percent aq. CF₃COOH / CHCl₃ / 0.25 h / 20 °C

5: 1.) Bu₂SnO, 2.) Et₄NBr / 1.) benzene, reflux, 2.) reflux

6: 95 percent / pyridine

7: 73 percent / Bu₄NBr, 4 Angstroem MS, CuBr₂ / CH₂Cl₂ / 72 h / 20 °C

With potassium hydroxide; 4 Angstroem MS; boron trifluoride diethyl etherate; tetraethylammonium bromide; tetrabutylammomium bromide; sodium methylate; sodium acetate; acetic anhydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; trifluoroacetic acid; copper(ll) bromide; In pyridine; dichloromethane; chloroform; dimethyl sulfoxide;

DOI:10.1007/bf02495661

Reference yield:

benzyl 3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (80035-35-4) → benzyl 6-O-[4-O-acetyl-3-O-(4-methoxybenzyl)-2-O-methyl-α-L-fucopyranosyl]-4-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (207917-29-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / Et₃N, DMAP / dimethylformamide / 0.5 h / 20 °C

2: 4 Angstroem MS, BF₃*Et₂O / acetonitrile; CH₂Cl₂ / 1 h / -40 °C

3: TsOH*H₂O / acetonitrile / 1 h / 50 °C

4: 73 percent / Bu₄NBr, 4 Angstroem MS, CuBr₂ / CH₂Cl₂ / 72 h / 20 °C

With dmap; 4 Angstroem MS; boron trifluoride diethyl etherate; tetrabutylammomium bromide; toluene-4-sulfonic acid; triethylamine; copper(ll) bromide; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1007/bf02495661

upstream raw materials:

ethyl 4-O-acetyl-3-O-(p-methoxybenzyl)-2-O-methyl-1-thio-β-L-fucopyranoside

benzyl 4-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

6-deoxy-L-galactose

benzyl 3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Downstream raw materials:

C₆₆H₇₆N₄O₁₆