phenyl [3,4-di-O-benzyl-2-O-(p-methoxybenzyl)-α-L-rhamnopyranosyl]-(1→3)-2,3,6-tri-benzoyl-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl [3,4-di-O-benzyl-2-O-(p-methoxybenzyl)-α-L-rhamnopyranosyl]-(1→3)-2,3,6-tri-benzoyl-1-thio-β-D-glucopyranoside
• CAS No.: 1437303-55-3
• Molecular Formula: C₆₁H₅₈O₁₃S
• Molecular Weight: 1031.19
• Mol file: 1437303-55-3.mol

Synonyms:phenyl [3,4-di-O-benzyl-2-O-(p-methoxybenzyl)-α-L-rhamnopyranosyl]-(1→3)-2,3,6-tri-benzoyl-1-thio-β-D-glucopyranoside

Chemical Property of phenyl [3,4-di-O-benzyl-2-O-(p-methoxybenzyl)-α-L-rhamnopyranosyl]-(1→3)-2,3,6-tri-benzoyl-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl [3,4-di-O-benzyl-2-O-(p-methoxybenzyl)-α-L-rhamnopyranosyl]-(1→3)-2,3,6-tri-benzoyl-1-thio-β-D-glucopyranoside

There total 5 articles about phenyl [3,4-di-O-benzyl-2-O-(p-methoxybenzyl)-α-L-rhamnopyranosyl]-(1→3)-2,3,6-tri-benzoyl-1-thio-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: 82.0%

ethyl 3,4-di-O-benzyl-2-O-(p-methoxybenzyl)-1-thio-α-L-rhamnoside (1437303-53-1) + phenyl 2,3,6-tri-O-benzoyl-1-thio-β-D-glucopyranoside → phenyl [3,4-di-O-benzyl-2-O-(p-methoxybenzyl)-α-L-rhamnopyranosyl]-(1→3)-2,3,6-tri-benzoyl-1-thio-β-D-glucopyranoside (1437303-55-3)

Guidance literature:

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -35 ℃; for 1h; stereoselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1016/j.tetasy.2013.04.001

Reference yield:

benzoyl cyanide (613-90-1) → phenyl [3,4-di-O-benzyl-2-O-(p-methoxybenzyl)-α-L-rhamnopyranosyl]-(1→3)-2,3,6-tri-benzoyl-1-thio-β-D-glucopyranoside (1437303-55-3)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / dichloromethane / 0 - 20 °C

2: N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -35 °C / Inert atmosphere; Molecular sieve

With pyridine; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane;

DOI:10.1016/j.tetasy.2013.04.001

Reference yield:

ethyl 3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside (130847-19-7) → phenyl [3,4-di-O-benzyl-2-O-(p-methoxybenzyl)-α-L-rhamnopyranosyl]-(1→3)-2,3,6-tri-benzoyl-1-thio-β-D-glucopyranoside (1437303-55-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / N,N-dimethyl-formamide / 3 h / 20 °C

2: N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -35 °C / Inert atmosphere; Molecular sieve

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; sodium hydroxide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tetasy.2013.04.001

upstream raw materials:

ethyl 3,4-di-O-benzyl-2-O-(p-methoxybenzyl)-1-thio-α-L-rhamnoside

phenyl 2,3-bis-O-benzoyl-1-thio-β-D-glucopyranoside

benzoyl cyanide

ethyl 3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside

Downstream raw materials:

phenyl [3,4-di-O-benzyl-2-O-(p-methoxybenzyl)-α-L-rhamnopyranosyl]-(1→3)-2,3,6-tribenzyl-1-thio-β-D-glucopyranoside

2-(p-methoxyphenoxy) ethyl (3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→4)-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1→3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside