methyl (3,4,6-tri-O-acetyl-2-trichloroacetamino-2-deoxy-β-D-glucopyranosyl)-(1->2)-(3,4-di-O-allyl-α-L-rhamnopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl(1->3)]-4-O-benzyl-α-L-rhamnopyranoside

Base Information

• Chemical Name: methyl (3,4,6-tri-O-acetyl-2-trichloroacetamino-2-deoxy-β-D-glucopyranosyl)-(1->2)-(3,4-di-O-allyl-α-L-rhamnopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl(1->3)]-4-O-benzyl-α-L-rhamnopyranoside
• CAS No.: 247092-77-9
• Molecular Formula: C₇₄H₈₈Cl₃NO₂₂
• Molecular Weight: 1449.87
• Mol file: 247092-77-9.mol

Synonyms:methyl (3,4,6-tri-O-acetyl-2-trichloroacetamino-2-deoxy-β-D-glucopyranosyl)-(1->2)-(3,4-di-O-allyl-α-L-rhamnopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl(1->3)]-4-O-benzyl-α-L-rhamnopyranoside

Chemical Property of methyl (3,4,6-tri-O-acetyl-2-trichloroacetamino-2-deoxy-β-D-glucopyranosyl)-(1->2)-(3,4-di-O-allyl-α-L-rhamnopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl(1->3)]-4-O-benzyl-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (3,4,6-tri-O-acetyl-2-trichloroacetamino-2-deoxy-β-D-glucopyranosyl)-(1->2)-(3,4-di-O-allyl-α-L-rhamnopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl(1->3)]-4-O-benzyl-α-L-rhamnopyranoside

There total 9 articles about methyl (3,4,6-tri-O-acetyl-2-trichloroacetamino-2-deoxy-β-D-glucopyranosyl)-(1->2)-(3,4-di-O-allyl-α-L-rhamnopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl(1->3)]-4-O-benzyl-α-L-rhamnopyranoside 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:

3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-α/β-D-glucopyranose trichloroacetimidate (161545-19-3) + methyl (3,4-di-O-allyl-α-L-rhamnopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl(1->3)]-4-O-benzyl-α-L-rhamnopyranoside (247092-76-8) → methyl (3,4,6-tri-O-acetyl-2-trichloroacetamino-2-deoxy-β-D-glucopyranosyl)-(1->2)-(3,4-di-O-allyl-α-L-rhamnopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl(1->3)]-4-O-benzyl-α-L-rhamnopyranoside (247092-77-9)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 0 - 20 ℃; under 89 Torr;

DOI:10.1080/07328309908544033

Reference yield:

2,3,4,6-tetra-O-benzyl-α/β-D-glucopyranosyl bromide (67773-43-7) → methyl (3,4,6-tri-O-acetyl-2-trichloroacetamino-2-deoxy-β-D-glucopyranosyl)-(1->2)-(3,4-di-O-allyl-α-L-rhamnopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl(1->3)]-4-O-benzyl-α-L-rhamnopyranoside (247092-77-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dibutyltin oxide / toluene / 3 h / Heating

1.2: 36 percent / Et₃NI / CH₂Cl₂ / 96 h

2.1: 96 percent / TMSOTf / diethyl ether / 15 h / -78 - 20 °C

3.1: 98 percent / MeONa / CH₂Cl₂; methanol / 48 h / 20 °C

4.1: TMSOTf / acetonitrile / 0 - 20 °C / 89 Torr

With trimethylsilyl trifluoromethanesulfonate; sodium methylate; di(n-butyl)tin oxide; In methanol; diethyl ether; dichloromethane; toluene; acetonitrile; 1.1: Metallation / 1.2: Substitution / 2.1: Substitution / 3.1: Hydrolysis / 4.1: Substitution;

DOI:10.1080/07328309908544033

Reference yield:

methyl 4-O-benzyl-α-L-rhamnopyranoside (25019-69-6) → methyl (3,4,6-tri-O-acetyl-2-trichloroacetamino-2-deoxy-β-D-glucopyranosyl)-(1->2)-(3,4-di-O-allyl-α-L-rhamnopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl(1->3)]-4-O-benzyl-α-L-rhamnopyranoside (247092-77-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dibutyltin oxide / toluene / 3 h / Heating

1.2: 36 percent / Et₃NI / CH₂Cl₂ / 96 h

2.1: 96 percent / TMSOTf / diethyl ether / 15 h / -78 - 20 °C

3.1: 98 percent / MeONa / CH₂Cl₂; methanol / 48 h / 20 °C

4.1: TMSOTf / acetonitrile / 0 - 20 °C / 89 Torr

With trimethylsilyl trifluoromethanesulfonate; sodium methylate; di(n-butyl)tin oxide; In methanol; diethyl ether; dichloromethane; toluene; acetonitrile; 1.1: Metallation / 1.2: Substitution / 2.1: Substitution / 3.1: Hydrolysis / 4.1: Substitution;

DOI:10.1080/07328309908544033

upstream raw materials:

3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-α/β-D-glucopyranose trichloroacetimidate

methyl (3,4-di-O-allyl-α-L-rhamnopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl(1->3)]-4-O-benzyl-α-L-rhamnopyranoside

2,3,4,6-tetra-O-benzyl-α/β-D-glucopyranosyl bromide

methyl 4-O-benzyl-α-L-rhamnopyranoside

Downstream raw materials:

methyl (2-amino-2-deoxy-β-D-glucopyranosyl)-(1-> 2)-(3,4-di-O-allyl-α-L-rhamnopyranosyl)-(1-> 2)-[(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1-> 3)]-4-O-benzyl-α-L-rhamnopyranoside

methyl (2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1-> 2)-(3,4-di-O-allyl-α-L-rhamnopyranosyl)-(1-> 2)-[(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1-> 3)]-4-O-benzyl-α-L-rhamnopyranoside

methyl (2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl)-(1-> 2)-(3,4-di-O-allyl-α-L-rhamnopyranosyl)-(1-> 2)-[(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1-> 3)]-4-O-benzyl-α-L-rhamnopyranoside

methyl (2-deoxy-4,6-O-isopropylidene-2-trichloroacetamido-β-D-glucopyranosyl)-(1-> 2)-(3,4-di-O-allyl-α-L-rhamnopyranosyl)-(1-> 2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1-> 3)]-4-O-benzyl-α-L-rhamnopyranoside