phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• CAS No.: 159734-75-5
• Molecular Formula: C₅₄H₅₀N₂O₁₅S
• Molecular Weight: 999.061
• Mol file: 159734-75-5.mol

Synonyms:phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property of phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

There total 3 articles about phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-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: 83.0%

thiophenol (108-98-5) + 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate (412021-79-5) → phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (159734-75-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In 1,2-dichloro-ethane; at 20 ℃; for 116h;

DOI:10.1016/S0040-4020(01)01148-6

Reference yield: 80.0%

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride (130539-42-3,147157-97-9,177966-56-2) + phenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (159734-70-0) → phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (159734-75-5)

Guidance literature:

With bis(cyclopentadienyl)hafnium dichloride; silver perchlorate; In dichloromethane; at -78 - 20 ℃;

DOI:10.1021/ja00105a066

Reference yield:

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-D-glucopyranose → phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (159734-75-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 399 mg / K₂CO₃ / 1,2-dichloro-ethane / 20 h / 20 °C

2: 83 percent / 4 Angstroem molecular sieves; TMSOTf / 1,2-dichloro-ethane / 116 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; potassium carbonate; In 1,2-dichloro-ethane;

DOI:10.1016/S0040-4020(01)01148-6

upstream raw materials:

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride

phenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

thiophenol

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate