120104-58-7

Basic information

• Product Name: 5-(Acetylamino)-2-chloro-2,5-dideoxy-3-S-phenyl-3-thio-D-erythro-α-L-gluco-2-nonulopyranosonic Acid Methyl Ester 4,7,8,9-Tetraacetate
• Synonyms: 5-(Acetylamino)-2-chloro-2,5-dideoxy-3-S-phenyl-3-thio-D-erythro-α-L-gluco-2-nonulopyranosonic Acid Methyl Ester 4,7,8,9-Tetraacetate;5-(Acetylamino)-2-chloro-2,5-dideoxy-3-S-phenyl-3-thio-D-erythro-a-L-gluco-2-nonulopyranosonic acid methyl ester 4,7,8,9-tetraacetate
• CAS NO: 120104-58-7
• Molecular Formula: C₂₆H₃₂ClNO₁₂S
• Molecular Weight: 618.04978
• Product Categories: Aromatics;Carbohydrates & Derivatives;Sulfur & Selenium Compounds
• Mol File: 120104-58-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 687.52°C at 760 mmHg
• Flash Point: 369.599°C
• Appearance: /
• Density: 1.37g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.555
• CAS DataBase Reference: 5-(Acetylamino)-2-chloro-2,5-dideoxy-3-S-phenyl-3-thio-D-erythro-α-L-gluco-2-nonulopyranosonic Acid Methyl Ester 4,7,8,9-Tetraacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(Acetylamino)-2-chloro-2,5-dideoxy-3-S-phenyl-3-thio-D-erythro-α-L-gluco-2-nonulopyranosonic Acid Methyl Ester 4,7,8,9-Tetraacetate(120104-58-7)
• EPA Substance Registry System: 5-(Acetylamino)-2-chloro-2,5-dideoxy-3-S-phenyl-3-thio-D-erythro-α-L-gluco-2-nonulopyranosonic Acid Methyl Ester 4,7,8,9-Tetraacetate(120104-58-7)

Safety Data

• Hazardous Substances Data: 120104-58-7(Hazardous Substances Data)

Usage

Uses

Intermediate in the preparation of STn epitope

InChI:InChI=1/C26H32ClNO12S/c1-13(29)28-20-22(21(38-16(4)32)19(37-15(3)31)12-36-14(2)30)40-26(27,25(34)35-6)24(23(20)39-17(5)33)41-18-10-8-7-9-11-18/h7-11,19-24H,12H2,1-6H3,(H,28,29)/t19-,20+,21-,22?,23+,24+,26+/m1/s1

Upstream product

• 108740-39-2 (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 
• 20298-34-4 methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosyl)onate 
• 73960-72-2 methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate 
• 931-59-9 benzenesulfenyl chloride 

Downstream Products

• 109681-25-6 methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 156726-98-6 Methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-3-(phenylthio)-D-erythro-β-L-gluco-2-nonulopyranosonate 
• 156726-99-7 Methyl onate 
• 133411-36-6 ethyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-β-L-gluco-2-nonulopyranosylonate)-(2->3)-2,4-di-O-acetyl-6-O-pivaloyl-β-D-galactopyranosyl-(1->4)-3-O-acetyl-2,6-di-O-pivaloyl-1-thio-β-D-glucopyranoside 
• 183019-40-1 (2R,3S,4R,5S,6R)-5-Acetylamino-4-benzoyloxy-6-((1R,2R)-3-benzoyloxy-1,2-dihydroxy-propyl)-2-fluoro-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 183019-39-8 (2R,3S,4R,5R,6R)-5-Acetylamino-6-((1R,2R)-3-benzoyloxy-1,2-dihydroxy-propyl)-2-fluoro-4-hydroxy-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 183019-41-2 (2R,3S,4R,5R,6R)-6-((1R,2R)-3-Acetoxy-1,2-dihydroxy-propyl)-5-acetylamino-2-fluoro-4-hydroxy-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 146788-04-7 (2R,3S,4R,5R,6R)-5-Acetylamino-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2-fluoro-4-hydroxy-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 146815-47-6 (2R,3S,4R,5R,6R)-5-Acetylamino-2-fluoro-4-hydroxy-3-phenylsulfanyl-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 133411-35-5 ethyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-β-L-gluco-2-nonulopyranosylonate)-(2->3)-6-O-pivaloyl-β-D-galactopyranosyl-(1->4)-2,6-di-O-pivaloyl-1-thio-β-D-glucopyranoside 
• 146815-49-8 Methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-S-phenyl-3-thio-β-D-erythro-L-gluco-2-nonulopyranosylonate)-(2->8)-(5-acetamido-4,7,9-tri-O-acetyl-5-deoxy-3-S-phenyl-3-thio-β-D-erythro-L-gluco-2-nonulopyranosyl)onate fluoride 
• 146788-06-9 (2R,3S,4R,5S,6R)-4-Acetoxy-5-acetylamino-6-((1R,2R)-1,3-diacetoxy-2-hydroxy-propyl)-2-fluoro-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 146815-48-7 (2R,3S,4R,5S,6R)-4-Acetoxy-6-[(S)-acetoxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-5-acetylamino-2-fluoro-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 146788-05-8 (2R,3S,4R,5S,6R)-4-Acetoxy-6-((1R,2R)-1-acetoxy-2,3-dihydroxy-propyl)-5-acetylamino-2-fluoro-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester 

Relevant articles and documents

An efficient short-step total synthesis of ganglioside GM3: Effective usage of the neighbouring group participation strategy

We have developed an efficient methodology for highly stereoselective sialylation using 3-position substituted sialic acids and have prepared 2a having a 3β-phenylthio group as a sialic donor. Glycosylation of suitably protected lactoside 3 with 2a gave only the α-sialyl trisaccharide 16 in good yield. Condensation of the azidosphingosine 4 with the acetate 17 using promotors, DMTST or NIS-TfOH, afforded the glycolipid 18, which was directly transformed to 20 by reduction with Bu3P and subsequent acylation with octadecanoic acid in the presence of WSC. Removal of the protecting groups generated ganglioside CM3 (1).

A New N-Acetylneuraminic Acid Donor for Highly Stereoselective α-Sialylation

The new sialyl donor 6 (prepared from N-acetylneuraminic acid in 44percent yield over six steps) effects clean α-sialylation of 2-(trimethylsilyl)ethyl 2,3,6,2',4',6'-hexabenzyl-β-D-lactoside in 67percent yield.