benzyl [(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid)-(2-> 3)-β-D-galactopyranosyl]-(1->-3)-2-acetamido-2-deoxy-α-D-galactopyranoside

Base Information

• Chemical Name: benzyl [(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid)-(2-> 3)-β-D-galactopyranosyl]-(1->-3)-2-acetamido-2-deoxy-α-D-galactopyranoside
• CAS No.: 290810-88-7
• Molecular Formula: C₃₂H₄₈N₂O₁₉
• Molecular Weight: 764.735
• Mol file: 290810-88-7.mol

Synonyms:benzyl [(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid)-(2-> 3)-β-D-galactopyranosyl]-(1->-3)-2-acetamido-2-deoxy-α-D-galactopyranoside

Chemical Property of benzyl [(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid)-(2-> 3)-β-D-galactopyranosyl]-(1->-3)-2-acetamido-2-deoxy-α-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl [(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid)-(2-> 3)-β-D-galactopyranosyl]-(1->-3)-2-acetamido-2-deoxy-α-D-galactopyranoside

There total 9 articles about benzyl [(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid)-(2-> 3)-β-D-galactopyranosyl]-(1->-3)-2-acetamido-2-deoxy-α-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: 72.0%

CMP-β-D-sialic acid disodium salt + (2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranosyl)-O-benzyl glycoside (3554-96-9) → benzyl [(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid)-(2-> 3)-β-D-galactopyranosyl]-(1->-3)-2-acetamido-2-deoxy-α-D-galactopyranoside (290810-88-7)

Guidance literature:

With α2,3OST Spodoptera frugiperda from rat liver; Triton X-100; In various solvent(s); at 37 ℃; pH=6;

DOI:10.1039/b514918e

Reference yield: 52.0%

C57H74N2O26 → benzyl [(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid)-(2-> 3)-β-D-galactopyranosyl]-(1->-3)-2-acetamido-2-deoxy-α-D-galactopyranoside (290810-88-7)

Guidance literature:

C₅₇H₇₄N₂O₂₆; With pyridine; lithium iodide; at 120 - 125 ℃; for 8h;

With acetic acid; In water; at 60 - 65 ℃; for 6h;

With sodium methylate; In methanol; at 20 ℃; for 24h;

DOI:10.1016/S0008-6215(00)00080-X

Reference yield:

benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>3)-2-acetamido-2-deoxy-α-D-galactopyranoside (90754-57-7,60831-31-4) → benzyl [(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid)-(2-> 3)-β-D-galactopyranosyl]-(1->-3)-2-acetamido-2-deoxy-α-D-galactopyranoside (290810-88-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 95 percent / pyridine / 12 h / 0 - 25 °C

2.1: 99 percent / CH₃ONa / methanol; CH₂Cl₂ / 0.33 h / -10 - -5 °C / pH 10

3.1: 73 percent / p-TsOH / acetonitrile / 8 h / 20 °C

4.1: 42 percent / NIS; 4 Angstroem-MS; TfOH / CH₂Cl₂; acetonitrile / 2 h / -45 - -40 °C

5.1: 78 percent / pyridine; DMAP / 12 h / 20 °C

6.1: LiI; pyridine / 8 h / 120 - 125 °C

6.2: HOAc / H₂O / 6 h / 60 - 65 °C

6.3: 52 percent / CH₃ONa / methanol / 24 h / 20 °C

With pyridine; dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 Angstroem-MS; sodium methylate; toluene-4-sulfonic acid; lithium iodide; In methanol; dichloromethane; acetonitrile; 1.1: Acylation / 2.1: Deacetylation / 3.1: Etherification / 4.1: Substitution / 5.1: Acylation / 6.1: Hydrolysis / 6.2: ether cleavage / 6.3: Deacetylation;

DOI:10.1016/S0008-6215(00)00080-X

upstream raw materials:

(2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranosyl)-O-benzyl glycoside

benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>3)-2-acetamido-2-deoxy-α-D-galactopyranoside

benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranoside

2,2-Dimethyl-propionic acid (2R,3R,4R,5R,6S)-5-acetylamino-6-benzyloxy-3-hydroxy-4-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester