methyl 2-acetamido-4-O-acetyl-6-O-benzyl-3-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-β-D-galactopyranoside

Base Information

• Chemical Name: methyl 2-acetamido-4-O-acetyl-6-O-benzyl-3-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-β-D-galactopyranoside
• CAS No.: 130257-44-2
• Molecular Formula: C₃₁H₄₁NO₁₆
• Molecular Weight: 683.664
• Mol file: 130257-44-2.mol

Synonyms:

Chemical Property of methyl 2-acetamido-4-O-acetyl-6-O-benzyl-3-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-acetamido-4-O-acetyl-6-O-benzyl-3-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-β-D-galactopyranoside

There total 5 articles about methyl 2-acetamido-4-O-acetyl-6-O-benzyl-3-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-β-D-galactopyranoside 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:

2,3,4-Tri-O-acetyl-β-D-glucopyranuronic acid methylester (3082-95-9,72692-06-9,73464-50-3) → methyl 2-acetamido-4-O-acetyl-6-O-benzyl-3-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-β-D-galactopyranoside (130257-44-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / 1,8-diazabicyclo5.4.0>undec-7-ene / 1,2-dichloro-ethane / 1 h / Ambient temperature

2: 72 percent / 1) activated powdered 4 Angstroem molecular sieves, 2) trimethylsilyl trifluoromethanesulfonate / 1) toluene, room temperature, 2) dichloromethane, -2O deg C, 1 h,

3: 82 percent / 24 h / Ambient temperature

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1,2-dichloro-ethane;

DOI:10.1016/0008-6215(90)84259-W

Reference yield:

(2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester (7355-18-2) → methyl 2-acetamido-4-O-acetyl-6-O-benzyl-3-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-β-D-galactopyranoside (130257-44-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / dibutyltin oxide / methanol / 0.75 h / 55 °C

2: 74 percent / 1,8-diazabicyclo5.4.0>undec-7-ene / 1,2-dichloro-ethane / 1 h / Ambient temperature

3: 72 percent / 1) activated powdered 4 Angstroem molecular sieves, 2) trimethylsilyl trifluoromethanesulfonate / 1) toluene, room temperature, 2) dichloromethane, -2O deg C, 1 h,

4: 82 percent / 24 h / Ambient temperature

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; di(n-butyl)tin oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; 1,2-dichloro-ethane;

DOI:10.1016/0008-6215(90)84259-W

Reference yield:

methyl 4-O-acetyl-2-azido-6-O-benzyl-2-deoxy-β-D-galactopyranoside (109914-58-1) → methyl 2-acetamido-4-O-acetyl-6-O-benzyl-3-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-β-D-galactopyranoside (130257-44-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / 1) activated powdered 4 Angstroem molecular sieves, 2) trimethylsilyl trifluoromethanesulfonate / 1) toluene, room temperature, 2) dichloromethane, -2O deg C, 1 h,

2: 82 percent / 24 h / Ambient temperature

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve;

DOI:10.1016/0008-6215(90)84259-W

upstream raw materials:

methyl 4-O-acetyl-2-azido-6-O-benzyl-2-deoxy-β-D-galactopyranoside

2,3,4-Tri-O-acetyl-β-D-glucopyranuronic acid methylester

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

(2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester