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

Base Information

• Chemical Name: 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
• CAS No.: 862980-92-5
• Molecular Formula: C₅₉H₇₁NO₂₀
• Molecular Weight: 1114.21
• Mol file: 862980-92-5.mol

Synonyms: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

Chemical Property of 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

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

There total 3 articles about 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 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: 82.0%

ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside (116514-50-2,128962-63-0,131545-02-3,136758-06-0,99409-34-4,116391-11-8) + 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) → 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 (862980-92-5)

Guidance literature:

With 4 A molecular sieve; methyl trifluoromethanesulfonate; In diethyl ether; at 20 ℃; for 18h;

DOI:10.1021/jo050707+

Reference yield:

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) → 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 (862980-92-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 20 °C

2: 80 percent / sodium cyanoborohydride; molecular sieves 4 Angstroem; hydrochloric acid / tetrahydrofuran; diethyl ether / 0 °C

3: 82 percent / methyl trifluoromethanesulfonate; molecular sieves 4 Angstroem / diethyl ether / 18 h / 20 °C

With hydrogenchloride; 4 A molecular sieve; sodium cyanoborohydride; N-ethyl-N,N-diisopropylamine; methyl trifluoromethanesulfonate; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo050707+

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-(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 (862980-92-5)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 82 percent / methyl trifluoromethanesulfonate; molecular sieves 4 Angstroem / diethyl ether / 18 h / 20 °C

With hydrogenchloride; 4 A molecular sieve; sodium cyanoborohydride; methyl trifluoromethanesulfonate; In tetrahydrofuran; diethyl ether;

DOI:10.1021/jo050707+

upstream raw materials:

ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside

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

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

Downstream raw materials:

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