N-Acetyl-2-O-methyl-a-neuraminic Acid Methyl Ester 4,7,8,9-Tetraacetate

Base Information

• Chemical Name: N-Acetyl-2-O-methyl-a-neuraminic Acid Methyl Ester 4,7,8,9-Tetraacetate
• CAS No.: 73208-80-7
• Molecular Formula: C21H31NO13
• Molecular Weight: 505.4697
• Mol file: 73208-80-7.mol

Synonyms:N-Acetyl-2-O-methyl-Alpha-neuraminic Acid Methyl Ester 4,7,8,9-Tetraacetate;N-Acetyl-2-O-methyl-a-neuraminic Acid Methyl Ester 4,7,8,9-Tetraacetate;N-Acetyl-2-O-methyl-α-neuraminic Acid Methyl Ester 4,7,8,9-Tetraacetate;

Chemical Property of N-Acetyl-2-O-methyl-a-neuraminic Acid Methyl Ester 4,7,8,9-Tetraacetate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 593.702°C at 760 mmHg
• Flash Point: 312.86°C
• PSA: 179.06000
• Density: 1.298g/cm³
• LogP: -0.45520
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Dichloromethane, Ether, Ethyl Acetate, Methanol

Purity/Quality:

99% ^*data from raw suppliers

N-Acetyl-2-O-methyl-a-neuraminic acid methyl ester 4,7,8,9-tetraacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Intermediate for the synthesis of supressor T cell inducers

Technology Process of N-Acetyl-2-O-methyl-a-neuraminic Acid Methyl Ester 4,7,8,9-Tetraacetate

There total 2 articles about N-Acetyl-2-O-methyl-a-neuraminic Acid Methyl Ester 4,7,8,9-Tetraacetate 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: 56.0%

methanol (67-56-1) + methyl <1-phenyl-1H-tetrazol-5-yl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid>onate (125532-26-5,125532-27-6) → methyl N-acetyl-4,7,8,9-tetra-O-acetyl-2-deoxy-2,3-dehydro-D-neuraminate (73960-72-2,78918-92-0,108812-69-7,108812-70-0,108812-71-1) + methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-nonulopyranosid)onate (41521-03-3,56323-64-9,73208-80-7,88547-02-8,99395-95-6,99395-96-7,99395-97-8,140385-82-6,140385-83-7,140385-84-8)

Guidance literature:

With 4 A molecular sieve; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In acetonitrile; for 24h;

DOI:10.1016/0008-6215(90)80045-5

Reference yield: 10.0%

methanol (67-56-1) + methyl <1-phenyl-1H-tetrazol-5-yl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid>onate (125532-26-5,125532-27-6) → methyl N-acetyl-4,7,8,9-tetra-O-acetyl-2-deoxy-2,3-dehydro-D-neuraminate (73960-72-2,78918-92-0,108812-69-7,108812-70-0,108812-71-1) + methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-nonulopyranosid)onate (41521-03-3,56323-64-9,73208-80-7,88547-02-8,99395-95-6,99395-96-7,99395-97-8,140385-82-6,140385-83-7,140385-84-8)

Guidance literature:

With 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; 1) 0 deg C, 4h, 2) RT, 20h;

DOI:10.1016/0008-6215(90)80045-5

Reference yield: 81.0%

benzaldehyde dimethyl acetal (1125-88-8) + methyl [methyl 4,7,8,9-tetra-O-acetyl-5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-non-2-ulopyranoside]onate (73208-80-7) → C20H27NO9

Guidance literature:

methyl [methyl 4,7,8,9-tetra-O-acetyl-5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-non-2-ulopyranoside]onate; With methanol; sodium methylate; at 20 ℃; for 0.5h;

benzaldehyde dimethyl acetal; With camphor-10-sulfonic acid; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1002/ejoc.201901587

upstream raw materials:

methanol

methyl <1-phenyl-1H-tetrazol-5-yl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid>onate

methyl <1-phenyl-1H-tetrazol-5-yl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid>onate

Downstream raw materials:

methyl α-glycoside of D-neuraminic acid

methyl α-glycoside of D-neuraminic acid

methyl 3,5-dideoxy-5-(2-hydroxyacetamido)-D-glycero-α-D-galacto-non-2-ulopyranosidonic acid

Neu5AcαOMe

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