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

Base Information

• Chemical Name: ethyl 3,4-di-O-benzyl-2-O-(p-methoxybenzyl)-1-thio-α-L-rhamnoside
• CAS No.: 1437303-53-1
• Molecular Formula: C₃₀H₃₆O₅S
• Molecular Weight: 508.679
• Mol file: 1437303-53-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about ethyl 3,4-di-O-benzyl-2-O-(p-methoxybenzyl)-1-thio-α-L-rhamnoside 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: 92.0%

ethyl 3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside (130847-19-7) + p-methoxybenzyl chloride (824-94-2) → ethyl 3,4-di-O-benzyl-2-O-(p-methoxybenzyl)-1-thio-α-L-rhamnoside (1437303-53-1)

Guidance literature:

With sodium hydroxide; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1016/j.tetasy.2013.04.001

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: 82.0%

ethyl 3,4-di-O-benzyl-2-O-(p-methoxybenzyl)-1-thio-α-L-rhamnoside (1437303-53-1) + 5-(benzyloxycarbonylamino)pentyl 4,6-O-benzylidene-2-deoxy-2-N-phthalimido-β-D-glucopyranoside → 5-(benzyloxycarbonylamino)pentyl (3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-β-D-glucopyranoside

Guidance literature:

ethyl 3,4-di-O-benzyl-2-O-(p-methoxybenzyl)-1-thio-α-L-rhamnoside; 5-(benzyloxycarbonylamino)pentyl 4,6-O-benzylidene-2-deoxy-2-N-phthalimido-β-D-glucopyranoside; In diethyl ether; dichloromethane; at 20 ℃; for 1h; Molecular sieve; Inert atmosphere;

With N-iodo-succinimide; silica-gel-supported sulfuric acid; In diethyl ether; dichloromethane; at -30 - 0 ℃; for 1h; stereoselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.tetlet.2018.12.019

upstream raw materials:

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

p-methoxybenzyl chloride

Downstream raw materials:

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