2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranosyl N-tosyl benzimidate

Base Information

• Chemical Name: 2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranosyl N-tosyl benzimidate
• CAS No.: 1393471-68-5
• Molecular Formula: C₃₄H₃₂N₂O₁₂S
• Molecular Weight: 692.7
• Mol file: 1393471-68-5.mol

Synonyms:2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranosyl N-tosyl benzimidate

Chemical Property of 2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranosyl N-tosyl benzimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranosyl N-tosyl benzimidate

There total 1 articles about 2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranosyl N-tosyl benzimidate 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%

N-(tolylsulfonyl)benzimidoyl chloride (4513-27-3) + 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose (72858-55-0,90405-21-3,90405-42-8,124362-60-3,144221-86-3) → 2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranosyl N-tosyl benzimidate (1393471-68-5)

Guidance literature:

With potassium carbonate; In acetone; at 20 ℃; for 2h; optical yield given as %de; stereoselective reaction;

DOI:10.1055/s-0031-1290920

Reference yield: 95.0%

p–tolyl 2,3-O-isopropylidene-1-thio-α-L-rhammopyranoside (903906-55-8) + 2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranosyl N-tosyl benzimidate (1393471-68-5) → tolyl O-(2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->4)-2,3-di-O-isopropylidene1-thio-α-L-rhamnopyranoside (1393471-89-0)

Guidance literature:

p-tolyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside; 2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranosyl N-tosyl benzimidate; In dichloromethane; for 0.5h; Molecular sieve; Inert atmosphere;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 2h; Molecular sieve; Inert atmosphere;

DOI:10.1055/s-0031-1290920

Reference yield: 93.0%

2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranosyl N-tosyl benzimidate (1393471-68-5) + 4-methoxy-phenol (150-76-5) → 4-methoxylphenzyl 2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranoside (138906-41-9)

Guidance literature:

2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranosyl N-tosyl benzimidate; 4-methoxy-phenol; In dichloromethane; for 0.5h; Molecular sieve; Inert atmosphere;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 2h; Molecular sieve; Inert atmosphere;

DOI:10.1055/s-0031-1290920

upstream raw materials:

N-(tolylsulfonyl)benzimidoyl chloride

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose

Downstream raw materials:

tolyl O-(2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->4)-2,3-di-O-isopropylidene1-thio-α-L-rhamnopyranoside

4-methoxylphenzyl 2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranoside

Refernces