Benzyl 2-Acetamido-2-deoxy-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-4,6-benzylidene-α-D-glucopyranoside

Base Information

• Chemical Name: Benzyl 2-Acetamido-2-deoxy-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-4,6-benzylidene-α-D-glucopyranoside
• CAS No.: 196941-73-8
• Molecular Formula: C49H53NO10
• Molecular Weight: 815.9458
• Mol file: 196941-73-8.mol

Synonyms:Benzyl 2-Acetamido-2-deoxy-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-4,6-benzylidene-α-D-glucopyranoside;PhenylMethyl 2-(AcetylaMino)-2-deoxy-3-O-[6-deoxy-2,3,4-tris-O-(phenylMethyl)-α-L-galactopyranosyl]-4,6-O-(phenylMethylene)-α-D-glucopyranoside

Chemical Property of Benzyl 2-Acetamido-2-deoxy-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-4,6-benzylidene-α-D-glucopyranoside

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 902.014°C at 760 mmHg
• PKA: 13.97±0.70(Predicted)
• Flash Point: 499.32°C
• PSA: 115.66000
• Density: 1.273g/cm³
• LogP: 8.27350

Purity/Quality:

98%Min ^*data from raw suppliers

Benzyl2-Acetamido-2-deoxy-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-4,6-benzylidene-α-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Benzyl 2-Acetamido-2-deoxy-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-4,6-benzylidene-α-D-glucopyranoside

There total 7 articles about Benzyl 2-Acetamido-2-deoxy-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-4,6-benzylidene-α-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: 87.5%

→ benzyl-2-acetamido-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (196941-73-8)

Guidance literature:

Reference yield: 76.0%

benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (78246-81-8) + 2-Pyridyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside (126330-74-3) → benzyl 2-acetamido-4,6-O-benzylidene-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-α-D-glucopyranoside (196941-73-8)

Guidance literature:

With methyl iodide; In dichloromethane; at 50 ℃; for 60h;

DOI:10.1039/a704310d

Reference yield:

benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (78246-81-8) + ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside (116514-50-2,128962-63-0,131545-02-3,136758-06-0,99409-34-4,116391-11-8) → benzyl 2-acetamido-4,6-O-benzylidene-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-α-D-glucopyranoside (196941-73-8)

Guidance literature:

ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside; With tetrabutylammomium bromide; copper(ll) bromide; In dichloromethane; N,N-dimethyl-formamide; at 21 ℃; for 4h; Molecular sieve;

benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside; In dichloromethane; N,N-dimethyl-formamide; at 21 ℃; for 64h; Molecular sieve;

DOI:10.1007/s11172-015-0990-7

upstream raw materials:

(2S,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-2-methyl-6-methylsulfanyl-tetrahydro-pyran

benzyl 4,6-O-benzylidene-2-acetylamino-2-deoxy-α-D-glucopyranoside

benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

2-Pyridyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside

Downstream raw materials:

2-acetamido-2-deoxy-3-O-(α-L-fucopyranosyl)-D-glucose

Refernces

• 1、 Baba,Iwata,Hamajima,Ikami,Ishida,Hasegawa,Kiso. "A convenient and efficient synthesis of sialyl Lewis X.". . p. 590 - 592. Retrieved 2007/10/03.
• 2、 Mereyala, Hari Babu,Gurrala, Srinivas Reddy,Gadikota, Rajendrakumar Reddy. "Stereoselective synthesis of α-O-fucosylated serine, threonine, tyrosine and saccharides". . p. 3179 - 3182. Retrieved 2007/10/03.