120104-58-7

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

• 120123-60-6 (2S,3S,4R,5S,6R)-4-Acetoxy-5-acetylamino-3-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 156726-99-7 Methyl onate 
• 195193-39-6 (2R,3S,4R,5S,6R)-4-Acetoxy-5-acetylamino-2-methylsulfanyl-3-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 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 
• 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 

Relevant academic research and scientific papers

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).

Highly stereoselective α-sialylation. Synthesis of GM3-saccharide and a bis-sialic acid unit

The novel sialyl donor methyl [ethyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-thio-3-(phenylthio)-2,3,5-trideox y-D-erythro-α-L-gluco-2-nonulopyranosid]onate (6) was synthesized in six steps from N-acetylneuraminic acid in an overall yield of 47%. Donor 6 was shown to be superior to conventional sialyl donors in that the sialylation yields were higher, even with sterically hindered and unreactive sialyl acceptors, and the α/β-selectivity was virtually complete.

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.

Efficient Synthesis of 2α-Glycoside od N-Acetylneuraminic Acid via Phenylsulfenyl Chloride Adduct of 2-Deoxy-2,3-dehydro-N-acetylneuraminic Acid Methyl Ester Tetra-O-acetate

Phenylsulfenyl chloride adds to a 2-deoxy-2,3-dehydro-N-acetylneuraminic acid derivative to give predominantly the corresponding 2-chloro-3β-phenylthio derivative, which is an excellent glycosyl donor for the preparation of α-glycosides of sialic acid.