2,4,7,8,9-Pentaacetyl-D-N-acetylglycolylneuraminic Acid Methyl Ester

Base Information

• Chemical Name: 2,4,7,8,9-Pentaacetyl-D-N-acetylglycolylneuraminic Acid Methyl Ester
• CAS No.: 118865-38-6
• Molecular Formula: C24H33 N O16
• Molecular Weight: 591.52
• Mol file: 118865-38-6.mol

Synonyms:D-glycero-D-galacto-2-Nonulopyranosonicacid, 5-[[(acetyloxy)acetyl]amino]-3,5-dideoxy-, methyl ester,2,4,7,8,9-pentaacetate

Chemical Property of 2,4,7,8,9-Pentaacetyl-D-N-acetylglycolylneuraminic Acid Methyl Ester

Chemical Property:

• Refractive Index: 1.505
• Boiling Point: 650.5±55.0 °C(Predicted)
• PKA: 11.74±0.70(Predicted)
• PSA: 222.43000
• Density: 1.35±0.1 g/cm3(Predicted)
• LogP: -0.99530
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, DMSO, Methanol

Purity/Quality:

97% ^*data from raw suppliers

2,4,7,8,9-Pentaacetyl-D-N-acetylglycolylneuraminic Acid Methyl Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2,4,7,8,9-Pentaacetyl-D-N-acetylglycolylneuraminic Acid Methyl Ester (cas# 118865-38-6) is a compound useful in organic synthesis.

Technology Process of 2,4,7,8,9-Pentaacetyl-D-N-acetylglycolylneuraminic Acid Methyl Ester

There total 1 articles about 2,4,7,8,9-Pentaacetyl-D-N-acetylglycolylneuraminic Acid Methyl Ester 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:

methanol (67-56-1) + 5-glycolylamido-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosylonic acid (80124-69-2) + acetic anhydride (108-24-7) → methyl (5-acetoxyacetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosyl)onate (118865-38-6)

Guidance literature:

With Amberlite IR-120 (H⁺) resin; Yield given. Multistep reaction; 1.) 2 d, 40 deg C, 2.) Py, room temperature, overnight;

DOI:10.1271/bbb.59.1091

Reference yield: 87.0%

thiophenol (108-98-5) + methyl (5-acetoxyacetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosyl)onate (118865-38-6) → methyl (phenyl 5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranoside)onate (299179-54-7)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; for 3h; Ambient temperature;

DOI:10.1271/bbb.59.1091

Reference yield:

methyl (5-acetoxyacetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosyl)onate (118865-38-6) → 2-(trimethylsilyl)ethyl O-(methyl 5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-6-O-benzoyl-β-D-galactopyranoside (170452-86-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / BF₃*OEt₂ / CH₂Cl₂ / 3 h / Ambient temperature

2: 54 percent / 1.) 3 Aengstroem molecular sieves, 2.) N-iodosuccinimide, trifluoromethanesulfonic acid / acetonitrile / 1.) 5 h, room temperature, room temperature to -35 deg C, 2.) -35 deg C, 4 h

With N-iodo-succinimide; trifluorormethanesulfonic acid; 3 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; acetonitrile;

DOI:10.1271/bbb.59.1091

upstream raw materials:

methanol

5-glycolylamido-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosylonic acid

acetic anhydride

Downstream raw materials:

methyl (phenyl 5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranoside)onate

2-(trimethylsilyl)ethyl O-(methyl 5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-6-O-benzoyl-β-D-galactopyranoside

methyl O-(methyl 5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-2,4,6-tri-O-benzoyl-1-thio-β-D-galactopyranoside

O-(methyl 5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-1-O-acetyl-2,4,6-tri-O-benzoyl-β-D-galactopyranose

Refernces