benzyl 6-deoxy-3,4-O-isopropylidene-2-O-(α-L-rhamnopyranosyl)-α-L-talopyranoside

Base Information

• Chemical Name: benzyl 6-deoxy-3,4-O-isopropylidene-2-O-(α-L-rhamnopyranosyl)-α-L-talopyranoside
• CAS No.: 88819-10-7
• Molecular Formula: C₂₂H₃₂O₉
• Molecular Weight: 440.491
• Mol file: 88819-10-7.mol

Synonyms:benzyl 6-deoxy-3,4-O-isopropylidene-2-O-(α-L-rhamnopyranosyl)-α-L-talopyranoside

Chemical Property of benzyl 6-deoxy-3,4-O-isopropylidene-2-O-(α-L-rhamnopyranosyl)-α-L-talopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 6-deoxy-3,4-O-isopropylidene-2-O-(α-L-rhamnopyranosyl)-α-L-talopyranoside

There total 4 articles about benzyl 6-deoxy-3,4-O-isopropylidene-2-O-(α-L-rhamnopyranosyl)-α-L-talopyranoside 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:

α-D-rhamnopyranose (643-17-4) → benzyl 6-deoxy-3,4-O-isopropylidene-2-O-(α-L-rhamnopyranosyl)-α-L-talopyranoside (88819-10-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / pyridine / Ambient temperature

2: 88 percent / HBr in acetic acid / CH₂Cl₂ / 3 h / 0 °C

3: 1.)silver triflate, 1,1,3,3-tetramethylurea / 1.) CH₂Cl₂, -20 deg C, 1 h; 2.) CH₂Cl₂, room temp.

With hydrogen bromide; silver trifluoromethanesulfonate; tetramethylurea; In pyridine; dichloromethane;

DOI:10.1016/0008-6215(83)84006-3

Reference yield:

1,2,3,4-tetra-O-acetyl-L-rhamnopyranose (1187858-70-3) → benzyl 6-deoxy-3,4-O-isopropylidene-2-O-(α-L-rhamnopyranosyl)-α-L-talopyranoside (88819-10-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / HBr in acetic acid / CH₂Cl₂ / 3 h / 0 °C

2: 1.)silver triflate, 1,1,3,3-tetramethylurea / 1.) CH₂Cl₂, -20 deg C, 1 h; 2.) CH₂Cl₂, room temp.

With hydrogen bromide; silver trifluoromethanesulfonate; tetramethylurea; In dichloromethane;

DOI:10.1016/0008-6215(83)84006-3

Reference yield:

benzyl 6-deoxy-3,4-O-isopropylidene-α-L-talopyranoside (88818-94-4) + 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl bromide (5158-64-5,14227-85-1,16741-27-8,24404-52-2,24877-07-4,36807-84-8,39524-38-4,41881-45-2,60978-06-5,69483-13-2,69980-52-5,75247-28-8,75247-29-9,80483-13-2,80483-14-3,89301-86-0,96648-29-2,108942-35-4,108942-38-7,138514-69-9) → benzyl 6-deoxy-3,4-O-isopropylidene-2-O-(α-L-rhamnopyranosyl)-α-L-talopyranoside (88819-10-7)

Guidance literature:

With silver trifluoromethanesulfonate; tetramethylurea; Yield given. Multistep reaction; 1.) CH₂Cl₂, -20 deg C, 1 h; 2.) CH₂Cl₂, room temp.;

DOI:10.1016/0008-6215(83)84006-3

upstream raw materials:

benzyl 6-deoxy-3,4-O-isopropylidene-α-L-talopyranoside

2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl bromide

α-D-rhamnopyranose

1,2,3,4-tetra-O-acetyl-L-rhamnopyranose

Downstream raw materials:

benzyl 6-deoxy-3,4-O-isopropylidene-2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-L-talopyranoside

benzyl 6-deoxy-2-O-(α-L-rhamnopyranosyl)-α-L-talopyranoside