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

Base Information

• Chemical Name: Methyl 4,7,8,9-tetra-O-acetyl-2-thio-N-acetyl-a-D-neuraminic acid methyl ester
• CAS No.: 116450-06-7
• Molecular Formula: C21H31 N O12 S
• Molecular Weight: 521.543
• Hs Code.: 29389090
• European Community (EC) Number: 634-215-1
• Nikkaji Number: J924.911G
• Wikidata: Q76416483
• Mol file: 116450-06-7.mol

Synonyms:116450-06-7;Methyl 4,7,8,9-tetra-O-acetyl-2-thio-N-acetyl-a-D-neuraminic acid methyl ester;methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-methylsulfanyl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate;alpha-Neuraminic acid, N-acetyl-2-S-methyl-2-thio-, methyl ester, 4,7,8,9-tetraacetate;W-200898;METHYL-4 7 8 9-TETRA-O-ACETYL-2-THIO -N-;N,4-O,7-O,8-O,9-O-Pentaacetyl-2-methylthio-2-deoxy-alpha-neuraminic acid methyl ester

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

Chemical Property:

• Melting Point: 80-84 °C
• Boiling Point: 609.9±55.0 °C(Predicted)
• PKA: 13.80±0.70(Predicted)
• PSA: 195.13000
• Density: 1.31±0.1 g/cm3(Predicted)
• LogP: 0.26140
• Storage Temp.: −20°C
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 15
• Exact Mass: 521.15669660
• Heavy Atom Count: 35
• Complexity: 833

Purity/Quality:

98%Min ^*data from raw suppliers

Methyl 4,7,8,9-tetra-O-acetyl-2-thio-N-acetyl-a-D-neuraminic acid methyl ester ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 45-46-23/24/25-36/37/38
• Safety Statements: 53-23-26-36/37/39-45

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)SC)OC(=O)C
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H](C[C@@](O[C@H]1[C@@H]([C@@H](COC(=O)C)OC(=O)C)OC(=O)C)(C(=O)OC)SC)OC(=O)C

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

There total 5 articles about Methyl 4,7,8,9-tetra-O-acetyl-2-thio-N-acetyl-a-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: 91.0%

2-Thiosialic acid methyl ester peracetate (104556-69-6) + methyl iodide (74-88-4) → methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate10,13 (116450-06-7)

Guidance literature:

2-Thiosialic acid methyl ester peracetate; With methanol; sodium; at -40 ℃; for 0.666667h;

methyl iodide; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/S0960-894X(00)00611-9

Reference yield:

N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester (67670-69-3) + sodium thiomethoxide (5188-07-8) → methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate (73960-72-2) + methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate10,13 (116450-06-7)

Guidance literature:

In acetonitrile; for 2h; Title compound not separated from byproducts;

DOI:10.1021/ja00084a003

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) → methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate10,13 (116450-06-7)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic anhydride, HCl / acetic acid / 16 h

2: acetonitrile / 2 h

With hydrogenchloride; acetic anhydride; In acetic acid; acetonitrile;

DOI:10.1021/ja00084a003

upstream raw materials:

N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester

sodium thiomethoxide

2-Thiosialic acid methyl ester peracetate

methyl iodide

Downstream raw materials:

methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

benzyl O--(2->3)-O-(2,6-di-O-benzyl-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside

benzyl O--(2->3)-O-(2,6-di-O-benzyl-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside