144002-21-1

Basic information

• Product Name: dibenzyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosidonate) phosphite
• Synonyms: dibenzyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosidonate) phosphite
• CAS NO: 144002-21-1
• Molecular Weight: 735.679
• Mol File: 144002-21-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: dibenzyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosidonate) phosphite(CAS DataBase Reference)
• NIST Chemistry Reference: dibenzyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosidonate) phosphite(144002-21-1)
• EPA Substance Registry System: dibenzyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosidonate) phosphite(144002-21-1)

Safety Data

• Hazardous Substances Data: 144002-21-1(Hazardous Substances Data)

Upstream product

• 84380-10-9 4,7,8,9-tetra-O-acetyl-N-acetylneuraminic acid methyl ester 
• 67746-43-4 dibenzyl N,N-diethylphosphoramidite 
• 19342-33-7 N-acetyl neuraminic acid 
• 20298-35-5 N-acetylneuraminic acid methyl ester 
• 6813-81-6 N-acetyl neuraminic acid 
• 108549-23-1 Dibenzyl N,N-diisopropylphosphoramidite 

Downstream Products

• 256426-89-8 4-acetoxy-5-acetylamino-2-[3-benzyloxy-2-(4-benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-4-yloxy]-6-(1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 1198096-97-7 C₄₀H₄₉NO₁₆ 
• 1416144-38-1 C₄₀H₄₉NO₁₆ 
• 906650-43-9 C₇₀H₈₀N₂O₂₃S 
• 215028-96-9 C₃₆H₄₅NO₁₈S 
• 221344-11-2 (1S,2S,4R,5S)-4-[(2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-methoxycarbonyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-yloxy]-5-hydroxy-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester 
• 216172-40-6 C₅₅H₆₅N₅O₂₁ 
• 156124-96-8 Methyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-3)-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)>-2,6-di-O-benzyl-β-D-glucopyrano... 
• 144002-22-2 methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-O-dibenzyloxyphosphoryl-3,5-dideoxy-β-D-glycero-D-galacto-non-2-ulopyranosonate 

Relevant articles and documents

Revealing Functional Significance of Interleukin-2 Glycoproteoforms Enabled by Expressed Serine Ligation

Naturally occurring interleukin-2 (IL-2) is a pleiotropic glycoprotein that regulates immune responses by controlling the differentiation and homeostasis of T cells. Non-glycosylated IL-2 has been used in clinical settings for three decades. However, the function of the O-glycan of native IL-2 remains elusive. Herein, to stress this issue, we report a highly efficient semi-synthesis of homogeneous glycosylated IL-2 with various glycoproteoforms on a multi-milligram scale. The glycopeptide fragment was prepared by chemical synthesis and then merged with recombinant fragment via a serine ligation to generate the desired glycoprotein in a single operation. Biological evaluation of the homogenous glycoprotein library reveals that the activity of IL-2 in activating individual T cell subset is glycan dependent, thus highlighting the possibility of further improving current clinical medicine.

A Total Synthesis of the Methyl Glycoside of Ganglioside GM

The total synthesis of the methyl glycoside of GM1 (1b) has been accomplished. The key step in the synthesis involves the sulfonamidoglycosidation reaction, which is used to create a β-linkage leading to a GalNAc residue joined to the C4 hydroxyl group of a galactose unit of a C3 sialylated lactosyl moiety. The "proximal hydroxyl" directing effect, which has been postulated before, manifests in this context as well leading to the preponderant formation of the β-glycoside. Together with asialo GM1 and other substructures, the GM1 methyl glycoside has been submitted for biological assays as potential ligands for bacterial and viral infection sites.

β-Sialyl phosphite and phosphoramidite: Synthesis and application to the chemoenzymatic synthesis of CMP-sialic acid and sialyl oligosaccharides

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