methyl (2R,4S,5R,6R)-5-acetamido-4-acetyloxy-2-chloro-6-[(1S,2S)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate

Base Information

• Chemical Name: methyl (2R,4S,5R,6R)-5-acetamido-4-acetyloxy-2-chloro-6-[(1S,2S)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS No.: 67670-69-3
• Molecular Formula: C20H28ClNO12
• Molecular Weight: 509.895
• European Community (EC) Number: 804-091-5
• Mol file: 67670-69-3.mol

Synonyms:67670-69-3;A929830;N-Acetyl-2-chloro-2-deoxy-?-neuraminic Acid Methyl Ester 4,7,8,9-Tetraacetate

Chemical Property of methyl (2R,4S,5R,6R)-5-acetamido-4-acetyloxy-2-chloro-6-[(1S,2S)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate

Chemical Property:

• Vapor Pressure: 1.53E-13mmHg at 25°C
• Boiling Point: 582.1°C at 760 mmHg
• Flash Point: 305.9°C
• PSA: 169.83000
• Density: 1.34g/cm³
• LogP: 0.13720
• Storage Temp.: Freezer
• Solubility.: Chloroform, Dichloromethane,
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 14
• Exact Mass: 509.1300030
• Heavy Atom Count: 34
• Complexity: 817

Purity/Quality:

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

N-Acetyl-2-chloro-2-deoxyneuraminic acid methyl ester 4,7,8,9-tetraacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 38

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)Cl)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)Cl)OC(=O)C
• Uses: Versatile sialic acid intermediate for the preparation of neuraminic acid derivatives. N-acetylneuraminic acid is often present as the terminal sugar of glycoproteins. Intermediate in the preparation of neuraminic acid derivatives

Technology Process of methyl (2R,4S,5R,6R)-5-acetamido-4-acetyloxy-2-chloro-6-[(1S,2S)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate

There total 34 articles about methyl (2R,4S,5R,6R)-5-acetamido-4-acetyloxy-2-chloro-6-[(1S,2S)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate 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: 100.0%

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) → N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester (67670-69-3)

Guidance literature:

With methanol; acetyl chloride; In dichloromethane; Large scale reaction;

DOI:10.1016/j.carres.2010.01.005

Reference yield: 100.0%

N-acetylneuraminic acid methyl ester (20298-35-5,22900-11-4,100678-43-1,109121-98-4,109122-00-1,119241-60-0,119241-61-1,119241-62-2) + acetyl chloride (75-36-5) → N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester (67670-69-3)

Guidance literature:

at 26 ℃; for 12h;

DOI:10.1021/ja00227a031

Reference yield: 100.0%

(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) → N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester (67670-69-3)

Guidance literature:

With hydrogenchloride; In dichloromethane; for 14h;

DOI:10.1021/jo035312+

upstream raw materials:

Methyl 5-acetamido-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosonate

acetyl chloride

N-acetylneuraminic acid methyl ester

(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

Downstream raw materials:

Methyl (3-methoxyphenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate

methyl (4-nitrophenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-oxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate

Methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate

Methyl-6-O-(4,7,8,9-tetra-O-acetyl-5-acetylamino-3,5-didesoxy-D-glycero-β-D-galakto-2-nonulopyranosidonsaeure-methylester)-2,3,4-tri-O-benzyl-β-D-glucopyranosid