p-methoxyphenyl 4-O-acetyl-2,3-O-isopropylidene-alpha-L-rhamnopyranosyl-(1->3)-4,6-O-benzylidene-2-deoxy-N-phthalimido-β-D-glucopyranoside

Base Information

• Chemical Name: p-methoxyphenyl 4-O-acetyl-2,3-O-isopropylidene-alpha-L-rhamnopyranosyl-(1->3)-4,6-O-benzylidene-2-deoxy-N-phthalimido-β-D-glucopyranoside
• CAS No.: 1359721-35-9
• Molecular Formula: C₃₉H₄₁NO₁₃
• Molecular Weight: 731.753
• Mol file: 1359721-35-9.mol

Synonyms:p-methoxyphenyl 4-O-acetyl-2,3-O-isopropylidene-alpha-L-rhamnopyranosyl-(1->3)-4,6-O-benzylidene-2-deoxy-N-phthalimido-β-D-glucopyranoside

Chemical Property of p-methoxyphenyl 4-O-acetyl-2,3-O-isopropylidene-alpha-L-rhamnopyranosyl-(1->3)-4,6-O-benzylidene-2-deoxy-N-phthalimido-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-methoxyphenyl 4-O-acetyl-2,3-O-isopropylidene-alpha-L-rhamnopyranosyl-(1->3)-4,6-O-benzylidene-2-deoxy-N-phthalimido-β-D-glucopyranoside

There total 1 articles about p-methoxyphenyl 4-O-acetyl-2,3-O-isopropylidene-alpha-L-rhamnopyranosyl-(1->3)-4,6-O-benzylidene-2-deoxy-N-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: 86.0%

p-tolyl 4-O-acetyl-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside (851625-43-9) + 4-methoxyphenyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (138906-43-1) → p-methoxyphenyl 4-O-acetyl-2,3-O-isopropylidene-alpha-L-rhamnopyranosyl-(1->3)-4,6-O-benzylidene-2-deoxy-N-phthalimido-β-D-glucopyranoside (1359721-35-9)

Guidance literature:

With N-iodo-succinimide; lanthanum(lll) triflate; In dichloromethane; at 20 ℃; for 0.75h; stereoselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.tetasy.2011.11.016

Reference yield:

p-methoxyphenyl 4-O-acetyl-2,3-O-isopropylidene-alpha-L-rhamnopyranosyl-(1->3)-4,6-O-benzylidene-2-deoxy-N-phthalimido-β-D-glucopyranoside (1359721-35-9) → p-methoxyphenyl 3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranosyl-(1->3)-4,6-O-benzylidene-2-deoxy-N-phthalimido-β-D-glucopyranoside (1359721-40-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium methylate / methanol / 0.5 h / 20 °C

1.2: DOWEX 50W H+ resin

2.1: N-iodo-succinimide; lanthanum(lll) triflate / dichloromethane / 0.75 h / -50 °C / Molecular sieve; Inert atmosphere

With N-iodo-succinimide; sodium methylate; lanthanum(lll) triflate; In methanol; dichloromethane;

DOI:10.1016/j.tetasy.2011.11.016

Reference yield:

p-methoxyphenyl 4-O-acetyl-2,3-O-isopropylidene-alpha-L-rhamnopyranosyl-(1->3)-4,6-O-benzylidene-2-deoxy-N-phthalimido-β-D-glucopyranoside (1359721-35-9) → p-methoxyphenyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranosyl-(1->3)-2-deoxy-N-phthalimido-4,6-O-benzylidene-β-D-glucopyranoside (1359721-42-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium methylate / methanol / 0.5 h / 20 °C

1.2: DOWEX 50W H+ resin

2.1: N-iodo-succinimide; lanthanum(lll) triflate / dichloromethane / 0.75 h / -50 °C / Molecular sieve; Inert atmosphere

3.1: sodium methylate / methanol / 0.5 h / 20 °C

3.2: DOWEX 50W H+ resin

With N-iodo-succinimide; sodium methylate; lanthanum(lll) triflate; In methanol; dichloromethane;

DOI:10.1016/j.tetasy.2011.11.016

upstream raw materials:

p-tolyl 4-O-acetyl-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

4-methoxyphenyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

Downstream raw materials:

p-methoxyphenyl 3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranosyl-(1->3)-4,6-O-benzylidene-2-deoxy-N-phthalimido-β-D-glucopyranoside

p-methoxyphenyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranosyl-(1->3)-2-deoxy-N-phthalimido-4,6-O-benzylidene-β-D-glucopyranoside