118977-26-7

Basic information

• Product Name: PER-O-ACETYL-ALPHA-THIOPHENYL-N-ACETYLNEURAMINIC METHYL ESTER
• Synonyms: PER-O-ACETYL-ALPHA-THIOPHENYL-N-ACETYLNEURAMINIC METHYL ESTER;Methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thiophenyl-D-glycero-a-D-galacto-2-nonulopyranosylonate;N-Acetyl-2-S-phenyl-2-thio-alpha-neuraminic acid methyl ester 4,7,8,9-tetraacetate
• CAS NO: 118977-26-7
• Molecular Formula: C₂₆H₃₃NO₁₂S
• Molecular Weight: 583.60472
• Mol File: 118977-26-7.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 671.0±55.0 °C(Predicted)
• Appearance: /
• Density: 1.32±0.1 g/cm3(Predicted)
• PKA: 13.79±0.70(Predicted)
• CAS DataBase Reference: PER-O-ACETYL-ALPHA-THIOPHENYL-N-ACETYLNEURAMINIC METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: PER-O-ACETYL-ALPHA-THIOPHENYL-N-ACETYLNEURAMINIC METHYL ESTER(118977-26-7)
• EPA Substance Registry System: PER-O-ACETYL-ALPHA-THIOPHENYL-N-ACETYLNEURAMINIC METHYL ESTER(118977-26-7)

Safety Data

• Hazardous Substances Data: 118977-26-7(Hazardous Substances Data)

Usage

Uses

N-Acetyl-?2-?S-?phenyl-?2-?thio-4,?7,?8,?9-?tetraacetate-α-?neuraminic Acid Methyl Ester is a useful reagent for stereoselective synthesis of 2-thioglycosides of N-acetylneuraminic acid.

Upstream product

• 67670-69-3 N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester 
• 108-98-5 thiophenol 
• 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 
• 6931-68-6 methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate 
• 19342-33-7 N-acetyl neuraminic acid 
• 20298-35-5 N-acetylneuraminic acid methyl ester 
• 84380-10-9 4,7,8,9-tetra-O-acetyl-N-acetylneuraminic acid methyl ester 
• 108-24-7 acetic anhydride 
• 4551-15-9 phenylthiotrimethylsilane 
• 107020-85-9 (4S,5R,6R)-4-Acetoxy-5-acetylamino-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 930-69-8 sodium thiophenolate 

Downstream Products

• 121512-93-4 [methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)onate] phenyl sulfone 
• 178425-76-8 C₅₉H₆₄N₂O₂₇S 
• 197663-24-4 O--(2->6)-O-(2-acetamido-3,4-di-O-acetyl-2-deoxy-α-D-galactopyranosyl)-(1->3)-N-(trichloroethoxycarbonyl)-L-serine benzyl ester 
• 202865-04-1 Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(5,6-dichloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester 
• 202865-08-5 p-methoxyphenyl O-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosyl) onate]-(2->3)-(2,4-di-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glu... 
• 243136-85-8 5-azido-3-oxapentyl (methyl [5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl]onate)-(2->6)-(2,3-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-2-acetamido-3-O-acetyl-6-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 145387-35-5 methyl (phenyl 5-acetamido-3,5-dideoxy-2-thio-D-glycero-α-D-galactonon-2-ulopyranoside)onate 
• 934415-78-8 methyl (phenyl 5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-α-D-galactonon-2-ulopyranoside)onate 
• 934591-83-0 methyl (phenyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-α-D-galactonon-2-ulopyranoside)onate 
• 934592-18-4 methyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ylopyranosylonate-(2->6)-methyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 934592-07-1 methyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosylonate-(2->6)-methyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 929882-35-9 methyl [2-thiophenyl 7,8,9-tri-O-acetyl-4,5-O,N-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside]onate 

Relevant articles and documents

Concise Synthesis of 1-Thioalkyl Glycoside Donors by Reaction of Per-O-acetylated Sugars with Sodium Alkanethiolates under Solvent-Free Conditions

A relatively green method for synthesizing 1-thioalkyl glycosides has been developed, where sodium alkanethiolates were used to react with per-O-acetylated sugars instead of odorous alkyl mercaptans in the presence of BF3·Et2O without the use of solvents under mild conditions. Furthermore, we found that 1,2-trans-β-thioglycosides can be converted into corresponding 1,2-cis-α-thioglycosides in the presence of trifluoromethanesulfonic acid in nonpolar solvents under mild conditions. This provides a simple and efficient new approach for synthesizing challenging 1,2-cis-α-thioglycosides.

Triflic acid-mediated synthesis of thioglycosides

An efficient synthesis of thioglycosides from per-acetates in the presence of triflic acid is described. The developed protocol features high reaction rates and product yields. Some reactive sugar series give high efficiency in the presence of sub-stoichiometric trifluoromethanesulfonic acid (TfOH) in contrast to other known protocols that require multiple equivalents of Lewis acids to reach high conversion rates.

Chemical Synthesis and Enzymatic Testing of CMP-Sialic Acid Derivatives

The cycloSal approach has been used in the past for the synthesis of a range of phosphorylated bioconjugates. In those reports, cycloSal nucleotides were allowed to react with different phosphate nucleophiles. With glycopyranosyl phosphates as nucleophile