Methyl5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate

Base Information

• Chemical Name: Methyl5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate
• CAS No.: 73960-72-2
• Molecular Formula: C20H27NO12
• Molecular Weight: 473.434
• Mol file: 73960-72-2.mol

Synonyms:Methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate;

Chemical Property of Methyl5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate

Chemical Property:

• Melting Point: 126-127°C
• Boiling Point: 571.8 °C at 760 mmHg
• PKA: 13.69±0.70(Predicted)
• Flash Point: 299.6 °C
• PSA: 169.83000
• Density: 1.31 g/cm³
• LogP: -0.30410

Purity/Quality:

98%Min ^*data from raw suppliers

Methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Methyl5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate

There total 125 articles about Methyl5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate 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: 95.0%

(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) → methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate (73960-72-2)

Guidance literature:

In dichloromethane; at 420 ℃; under 48.7549 - 67.5068 Torr; Pyrolysis;

DOI:10.1021/jo900224t

Reference yield: 95.0%

N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester (67670-69-3) → methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate (73960-72-2)

Guidance literature:

With disodium hydrogenphosphate; In acetonitrile; for 3h; Heating;

DOI:10.1055/s-2006-950354

Reference yield: 95.0%

(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) → methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate (73960-72-2)

Guidance literature:

(4S,5R,6R)-4-Acetoxy-5-acetylamino-2-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester; With dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In dichloromethane; at -20 ℃; for 2h;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at -20 - 20 ℃;

DOI:10.1248/cpb.48.163

upstream raw materials:

cyclohexylmethyl trimethylsilyl ether

benzyl 2,6-di-O-benzyl-β-D-galactopyranoside

methyl (ethyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosid)onate

O-ethyl S-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)onate] dithiocarbonate

Downstream raw materials:

2,3-dehydro-2-deoxy-N-acetylneuraminic acid

methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate

5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonic acid

(3R,4R,5S,6R)-4-Acetoxy-5-acetylamino-2-chloro-3-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Refernces

• 1、 Shpirt,Kononov,Torgov,Shibaev. "Selective formation of α-glycosyl phosphate from N-acetylneuraminic acid glycosyl chloride [2]". . p. 481 - 482. Retrieved 2005.
• 2、 Kulikova, Nadezhda Yu.,Shpirt, Anna M.,Kononov, Leonid O.. "A facile synthesis of N-acetylneuraminic acid glycal". . p. 4113 - 4114. Retrieved 2006.
• 3、 Sengupta, Prabal,Misra, Anup Kumar,Suzuki, Misa,Fukuda, Minoru,Hindsgaul, Ole. "Chemoenzymatic synthesis of sialylated oligosaccharides for their evaluation in a polysialyltransferase assay". . p. 6037 - 6042. Retrieved 2003.
• 4、 Asressu, Kesatebrhan Haile,Chang, Chun-Wei,Lam, Sarah,Wang, Cheng-Chung. "Donor-Reactivity-Controlled Sialylation Reactions". . p. 4525 - 4530. Retrieved 2021/08/09.
• 5、 Manna, Tapasi,Misra, Anup Kumar. "Synthesis of the sialylated pentasaccharide repeating unit of the capsular polysaccharide of Streptococcus group B type VI". . . Retrieved 2021/03/29.