methyl (3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(4-methoxyphenyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate

Base Information

• Chemical Name: methyl (3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(4-methoxyphenyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate
• CAS No.: 273401-00-6
• Molecular Formula: C₄₂H₄₂Cl₃NO₁₈
• Molecular Weight: 955.15
• Mol file: 273401-00-6.mol

Synonyms:methyl (3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(4-methoxyphenyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate

Chemical Property of methyl (3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(4-methoxyphenyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(4-methoxyphenyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate

There total 2 articles about methyl (3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(4-methoxyphenyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate 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: 77.0%

methyl (4-methoxyphenyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate (181584-02-1) + phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-trichloroacetamido-β-D-galactopyranoside (198200-67-8) → methyl (3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(4-methoxyphenyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate (273401-00-6)

Guidance literature:

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/S0008-6215(99)00322-5

Reference yield:

phenyl 2-deoxy-1-thio-2-trichloroacetamido-β-D-galactopyranoside → methyl (3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(4-methoxyphenyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate (273401-00-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / pyridine / 20 °C

2: 77 percent / N-iodosuccinimide; 4 Angstroem molecular sieves; Me₃SiOTf / CH₂Cl₂ / 1 h / 20 °C

With pyridine; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; 1: Acetylation / 2: Etherification;

DOI:10.1016/S0008-6215(99)00322-5

Reference yield: 86.0%

methyl (3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(4-methoxyphenyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate (273401-00-6) → (2S,3S,4S,5R)-4,5-Bis-benzoyloxy-3-[(2S,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-2-yloxy]-6-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:

With ammonium cerium(IV) nitrate; In water; toluene; acetonitrile; at 20 ℃; for 0.75h;

DOI:10.1016/S0008-6215(00)00032-X

upstream raw materials:

methyl (4-methoxyphenyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate

phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-trichloroacetamido-β-D-galactopyranoside

Downstream raw materials:

methyl (3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-2,3-di-O-benzoyl-1-O-trichloroacetimidoyl-α-D-glucopyranuronate