Phenyl 4,7,8,9-tetra-O-acetyl-2-thio-N-acetyl-D-neuraminic acid methyl ester

Base Information

• Chemical Name: Phenyl 4,7,8,9-tetra-O-acetyl-2-thio-N-acetyl-D-neuraminic acid methyl ester
• CAS No.: 155155-64-9
• Molecular Formula: C26H33 N O12 S
• Molecular Weight: 583.614
• DSSTox Substance ID: DTXSID10471287
• Nikkaji Number: J1.308.194H
• Mol file: 155155-64-9.mol

Synonyms:155155-64-9;Phenyl 4,7,8,9-tetra-O-acetyl-2-thio-N-acetyl-D-neuraminic acid methyl ester;Methyl (Phenyl 5-Acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate;methyl (4S,5R,6R)-5-acetamido-4-acetyloxy-2-phenylsulfanyl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate;Methyl 5-Acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-S-phenyl-2-thio-D-glycero-D-galacto-2-nonulopyranosylonate;Neuraminic acid, N-acetyl-2-S-phenyl-2-thio-, methyl ester, 4,7,8,9-tetraacetate;Phenyl 4,7,8,9-tetra-O-acetyl-2-thio-N-acetyl-a-D-neuraminic acid methyl ester;METHYL (PHENYL 5-ACETAMIDO-4,7,8,9-TETRA-O-ACETYL-3,5-DIDEOXY-2-THIO-D-GLYCERO-D-GALACTO-2-NONULOPYR;Neu5Ac[1Me,4789Ac]-SPh;DTXSID10471287;CS-0154022;M1706;T71847;W-201398;N-Acetyl-2-phenylthioneuraminic acid, methyl ester, 4,7,8,9-tetraacetate;Methyl phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-galacto-non-2-ulopyranosidonate;Methyl(Phenyl5-Acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate

Chemical Property of Phenyl 4,7,8,9-tetra-O-acetyl-2-thio-N-acetyl-D-neuraminic acid methyl ester

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 183 °C
• Refractive Index: -121 ° (C=1, CHCl3)
• Boiling Point: 670.995oC at 760 mmHg
• PKA: 13.79±0.70(Predicted)
• Flash Point: 359.605oC
• PSA: 195.13000
• Density: 1.329g/cm3
• LogP: 1.69070
• Storage Temp.: Freezer
• Solubility.: soluble in Chloroform
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 16
• Exact Mass: 583.17234666
• Heavy Atom Count: 40
• Complexity: 952

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl 5-Acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-S-phenyl-2-thio-D-glycero-D-galacto-2-nonulopyranosylonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C(CC(OC1C(C(COC(=O)C)OC(=O)C)OC(=O)C)(C(=O)OC)SC2=CC=CC=C2)OC(=O)C
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H](CC(O[C@H]1[C@@H]([C@@H](COC(=O)C)OC(=O)C)OC(=O)C)(C(=O)OC)SC2=CC=CC=C2)OC(=O)C
• Uses: Methyl 5-Acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-S-phenyl-2-thio-D-glycero-D-galacto-2-nonulopyranosylonate (CAS# 155155-64-9) is a useful building block used in the preparation of ganglioside GM3 analogs.

Technology Process of Phenyl 4,7,8,9-tetra-O-acetyl-2-thio-N-acetyl-D-neuraminic acid methyl ester

There total 3 articles about Phenyl 4,7,8,9-tetra-O-acetyl-2-thio-N-acetyl-D-neuraminic 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: 89.0%

methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate (6931-68-6,72690-21-2,74006-95-4,108740-37-0,108740-38-1,108740-39-2,119241-63-3,119241-64-4,119241-65-5,147129-72-4,147129-73-5,73208-82-9) + thiophenol (108-98-5) → (4S,5R,6R)-4-Acetoxy-5-acetylamino-2-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (155155-64-9)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1016/j.tetlet.2007.08.088

Reference yield: 56.0%

methyl acetochloroneuraminate (59367-09-8) + diphenyldisulfane (882-33-7) → (4S,5R,6R)-4-Acetoxy-5-acetylamino-2-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (155155-64-9)

Guidance literature:

diphenyldisulfane; With zinc(II) chloride; zinc; In acetonitrile; at 70 ℃; for 0.75h;

methyl acetochloroneuraminate; In acetonitrile; at 70 ℃; for 1h;

DOI:10.1016/j.tetlet.2005.11.074

Reference yield:

(1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate (108740-39-2,6931-68-6,72690-21-2,73208-82-9,108740-37-0,108740-38-1,119241-63-3,119241-64-4,119241-65-5,147129-72-4,147129-73-5,74006-95-4) + thiophenol (108-98-5) → (4S,5R,6R)-4-Acetoxy-5-acetylamino-2-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (155155-64-9)

Guidance literature:

With boron trifluoride diethyl etherate;

DOI:10.1023/a:1024855917480

upstream raw materials:

(1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate

thiophenol

methyl acetochloroneuraminate

diphenyldisulfane

Downstream raw materials:

2-(Trimethylsilyl)ethyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(1->6)-O-(2-acetamido-2-deoxy-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)...

(2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-[(2R,4aR,6R,7R,8R,8aS)-7-hydroxy-2-phenyl-6-(2-trimethylsilanyl-ethoxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

5-azidopentyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-(2->3)-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Refernces

• 1、 Mukherjee, Chinmoy,Tiwari, Pallavi,Misra, Anup Kumar. "Synthesis of thio- and selenoglycosides by cleavage of dichalconides in the presence of zinc/zinc chloride and reaction with glycosyl bromides". . p. 441 - 445. Retrieved 2007/10/03.