100938-57-6

Basic information

• Product Name: (2S,3R)-2-Amino-3-((2S,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-butyric acid benzyl ester
• Synonyms: (2S,3R)-2-Amino-3-((2S,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-butyric acid benzyl ester
• CAS NO: 100938-57-6
• Molecular Weight: 538.552
• Mol File: 100938-57-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (2S,3R)-2-Amino-3-((2S,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-butyric acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R)-2-Amino-3-((2S,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-butyric acid benzyl ester(100938-57-6)
• EPA Substance Registry System: (2S,3R)-2-Amino-3-((2S,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-butyric acid benzyl ester(100938-57-6)

Safety Data

• Hazardous Substances Data: 100938-57-6(Hazardous Substances Data)

Upstream product

• 67673-39-6 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl bromide 
• 73724-48-8 N-(fluoren-9-ylmethoxycarbonyl)-L-threonine benzyl ester 
• 213331-76-1 (2S,3R)-3-((3aR,4R,6S,7R,7aR)-7-Azido-2,2-dimethyl-4-triisopropylsilanyloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester 
• 218291-41-9 N^α-fluoren-9-ylmethoxycarbonyl-O-(2-azido-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester 
• 67817-37-2 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl chloride 
• 67817-41-8 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl chloride 

Downstream Products

• 129432-11-7 N-<2-(4-pyridyl)ethoxycarbonyl>-L-alanyl-L-alanyl-O-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester 
• 100929-13-3 N-<2-(4-pyridyl)ethoxycarbonyl>-L-seryl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-seryl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester 
• 218291-45-3 C₅₈H₇₀N₄O₂₃ 
• 129415-19-6 C₄₅H₆₃N₅O₂₃ 
• 100929-15-5 N,O-diacetyl-L-seryl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galctopyranosyl)-L-seryl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-threonine benzylester 
• 1436867-96-7 C₂₀H₃₃N₃O₁₀ 
• 1426832-53-2 c[L-aspartyl-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-threonyl] 
• 1426832-55-4 C₄₈H₅₇N₃O₁₆ 

Relevant articles and documents

α-Selective glycosylation affords mucin-related GalNAc amino acids and diketopiperazines active on Trypanosoma cruzi

This work addresses the synthesis and biological evaluation of glycosyl diketopiperazines (DKPs) cyclo[Asp-(αGalNAc)Ser] 3 and cyclo[Asp-(αGalNAc)Thr] 4 for the development of novel anti-trypanosomal agents and Trypanosoma cruzi trans-sialidase (TcTS) inhibitors. The target compounds were synthetized by coupling reactions between glycosyl amino acids αGalNAc-Ser 7 or αGalNAc-Thr 8 and the amino acid (O-tBu)-Asp 17, followed by one-pot deprotection-cyclisation reaction in the presence of 20% piperidine in DMF. The protected glycosyl amino acid intermediates 7 and 8 were, in turn, obtained by α-selective, HgBr2-catalysed glycosylation reactions of Fmoc-Ser/Thr benzyl esters 12/14 with αGalN3Cl 11, being, subsequently, fully deprotected for comparative biological assays. The DKPs 3 and 4 showed relevant anti-trypanosomal effects (IC50 282-124 μM), whereas glycosyl amino acids 1 and 2 showed better TcTS inhibition (57-79%) than the corresponding DKPs (13-25%).

Synthesis of glycopeptides with the TN and T antigen structures, and their coupling to bovine serum albumin.

Glycopeptides with TN and T antigen structures that represent the N-terminal tripeptide of asialoglycophorin with blood-group M specificity have been synthesized using fluorenylmethoxycarbonyl (Fmoc) and 2-pyridylethoxycarbonyl (Pyoc) groups for amino pro