172316-09-5

Basic information

• Product Name: 2,4-di-O-benzyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide
• Synonyms: 2,4-di-O-benzyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide
• CAS NO: 172316-09-5
• Molecular Weight: 1328.44
• Mol File: 172316-09-5.mol

Chemical Properties

• CAS DataBase Reference: 2,4-di-O-benzyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-di-O-benzyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide(172316-09-5)
• EPA Substance Registry System: 2,4-di-O-benzyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide(172316-09-5)

Safety Data

• Hazardous Substances Data: 172316-09-5(Hazardous Substances Data)

Upstream product

• 1294354-20-3 2-O-benzyl-4,6-O-benzylidene-3-O-((4-methoxyphenyl)methyl)-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 
• 1365547-59-6 3,6-di-O-acetyl-2,4-di-O-benzyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 

Relevant articles and documents

A practical and efficient synthesis of complex-type biantennary heptasaccharide-asparagine conjugate, a-key building block for the synthesis of complex N-linked glycopeptides

The complex-type biantennary heptasaccharide-asparagine conjugate(2) of N-linked glycoproteins was synthesized from monosaccharide units 3, 4, 6, 7 and 8 in 7 steps with an overall yield of 18.4%.

Solid-phase synthesis of CD52 glycopeptide and an efficient route to Asn-core pentasaccharide conjugate

The intact peptide sequence (18) as well as its glycoform carrying an N- linked core pentasaccharide (1) of CD52 antigen were prepared by means of solid-phase synthesis employing Fmoc-amino acids and benzyl-protected oligosaccharide-asparagine conjugate (

Synthesis of fully O-benzylated N-linked core pentasaccharide glycosyl azide

The fully O-benzylated pentasaccharide glycosyl azide representing the common core structure of N-glycans was synthesized. The β-mannosidic linkage was created by C-2 epimerization of the initially introduced β-d-gluco-unit via DMSO/Ac2O oxidat

Synthesis of biantennary complex-type nonasaccharyl asn building blocks for solid-phase glycopeptide synthesis

The biantennary complex-type N-glycans bearing LacNAc and LacdiNAc as the nonreducing end motif were synthesized in a protected form suitable to use in the Fmoc solid-phase peptide synthesis studies. Two approaches for the nonasaccharide synthesis were examined by taking advantage of the highly β-selective glycosylation with GlcNTCA (N-phenyl)trifluoroacetimidate. An earlier approach, which involved the reaction of the trisaccharide donor (Gal-GlcNTCA-Man) and trisaccharide acceptor (Man-GlcNPhth2-N 3), produced a mixture of nonasaccharide isomers. On the other hand, mannosylation of the trisaccharide acceptor (Man-GlcNPhth2-N 3) stereoselectively afforded the known pentasaccharide (Man 3-GlcNPhth2-N3), which was reacted with the disaccharyl glycosyl donor (Gal-GlcNTCA or GalNTCA-GlcNTCA) to produce the desired nonasaccharide as a single stereoisomer. Selective dephthaloylation followed by N-acetylation furnished the GlcNAc2 functionality. The resulting nonasaccharyl azides were condensed with Fmoc-Asp(OPfp)-OBu t or Fmoc-Asp(OPfp)-OPac in the presence of Ph(CH3) 2P and HOOBt. Finally, the Zn reduction and cleavage of the tert-butyl ester or Zn reduction alone produced the targeted nonasaccharyl Asn building blocks.

6-Nitro-2-benzothiazolyl α-mannoside: A highly efficient mannosyl donor in constructing β-Man(1→4)GlcN linkage and its application to the synthesis of the pentasaccharide core of N-glycans

An efficient and concise synthesis of the β-Man(1→4)GlcN linkage that exists in N-linked glycans has been established. Direct β-mannosylations of the 4-OH group of glucosamine derivatives by using 6-nitro-2-benzothiazolyl 3,6-di-O-allyl-2,4-di-O-benzyl-α-