methyl 2-(N-acetylacetamido)-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: methyl 2-(N-acetylacetamido)-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
• CAS No.: 581797-49-1
• Molecular Formula: C₃₂H₄₁NO₁₆
• Molecular Weight: 695.675
• Mol file: 581797-49-1.mol

Synonyms:methyl 2-(N-acetylacetamido)-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

Chemical Property of methyl 2-(N-acetylacetamido)-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-(N-acetylacetamido)-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

There total 1 articles about methyl 2-(N-acetylacetamido)-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-4,6-O-benzylidene-2-deoxy-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: 94.0%

methyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside (98856-39-4) + acetyl chloride (75-36-5) → methyl 2-(N-acetylacetamido)-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (581797-49-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine;

DOI:10.1021/ol034669x

Reference yield: 80.0%

methyl 2-(N-acetylacetamido)-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (581797-49-1) → methyl 2-(N-acetylacetamido)-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-6-O-benzyl-2-deoxy-β-D-glucopyranoside (581797-50-4)

Guidance literature:

With hydrogenchloride; sodium cyanoborohydride; In diethyl ether;

DOI:10.1021/ol034669x

Reference yield:

methyl 2-(N-acetylacetamido)-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (581797-49-1) → methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(β-D-galactopyranosyl)-4-O-(α-L-rhamnopyranosyl)-β-D-glucopyranoside (581797-52-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / sodium cyanoborohydride; molecular sieves 4 Angstroem; hydrochloric acid / tetrahydrofuran; diethyl ether / 0 °C

2: 91 percent / triethylsilyltrifluoromethanesulfonate; molecular sieves 4 Angstroem / CH₂Cl₂ / 2 h / -78 - 20 °C

3: 100 percent / sodium methoxide / methanol / 0.5 h / 20 °C

With hydrogenchloride; 4 A molecular sieve; triethylsilyl trifluoromethyl sulfonate; sodium methylate; sodium cyanoborohydride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1021/jo050707+

upstream raw materials:

methyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

acetyl chloride

Downstream raw materials:

methyl 2-(N-acetylacetamido)-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-6-O-benzyl-2-deoxy-β-D-glucopyranoside

methyl 2-acetamido-6-O-benzyl-4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-3-O-(β-D-galactopyranosyl)-β-D-glucopyranoside

methyl 2-(N-acetylacetamido)-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-6-O-benzyl-4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-β-D-glucopyranoside

methyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(β-D-galactopyranosyl)-4-O-(α-L-rhamnopyranosyl)-β-D-glucopyranoside