2-(trimethylsilyl)ethyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

Base Information

• Chemical Name: 2-(trimethylsilyl)ethyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS No.: 174392-90-6
• Molecular Formula: C₂₆H₃₁NO₇Si
• Molecular Weight: 497.62
• Mol file: 174392-90-6.mol

Synonyms:2-(trimethylsilyl)ethyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

Chemical Property of 2-(trimethylsilyl)ethyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(trimethylsilyl)ethyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

There total 1 articles about 2-(trimethylsilyl)ethyl 4,6-O-benzylidene-2-deoxy-2-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: 88.0%

benzaldehyde dimethyl acetal (1125-88-8) + 2-(trimethylsilyl)ethyl 2-deoxy-2-phthalimido-β-D-glucopyranoside (117252-99-0) → 2-(trimethylsilyl)ethyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (174392-90-6)

Guidance literature:

With iodine; In acetonitrile; at 20 ℃; for 1h;

DOI:10.1080/07328300802030837

Reference yield: 100.0%

ethyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside (125520-01-6) + 2-(trimethylsilyl)ethyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (174392-90-6) → 2-(trimethylsilyl)ethyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:

ethyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside; 2-(trimethylsilyl)ethyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside; In dichloromethane; at 20 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

With N-iodo-succinimide; silver trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1039/c8ob00316e

Reference yield: 96.0%

phenyl 2,3-di-O-benzyl-4,6-O-di-tert-butylsilylene-1-thio-β-L-galactopyranoside + 2-(trimethylsilyl)ethyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (174392-90-6) → 2-(trimethylsilyl)ethyl (2,3-di-O-benzyl-4,6-O-di-tert-butylsilylene-α-L-galactopyranosyl)-(1→3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:

phenyl 2,3-di-O-benzyl-4,6-O-di-tert-butylsilylene-1-thio-β-L-galactopyranoside; 2-(trimethylsilyl)ethyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside; With N-iodo-succinimide; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere; Molecular sieve;

With trifluorormethanesulfonic acid; In dichloromethane; at -20 ℃; for 0.5h; Inert atmosphere; Molecular sieve;

DOI:10.1039/d0ob01128b

upstream raw materials:

benzaldehyde dimethyl acetal

2-(trimethylsilyl)ethyl 2-deoxy-2-phthalimido-β-D-glucopyranoside

Downstream raw materials:

2-(trimethylsilyl)ethyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

2-trimethylsilylethyl 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

2-(trimethylsilyl)ethyl 3-O-allyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

2-(trimethylsilyl)ethyl 4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside