402948-42-9

Basic information

• Product Name: methyl [phenyl 5-(2,2,2-trichloroethoxycarbonylamino)-3,5-dideoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid]onate
• Synonyms: methyl [phenyl 5-(2,2,2-trichloroethoxycarbonylamino)-3,5-dideoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid]onate
• CAS NO: 402948-42-9
• Molecular Weight: 548.826
• Mol File: 402948-42-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: methyl [phenyl 5-(2,2,2-trichloroethoxycarbonylamino)-3,5-dideoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid]onate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl [phenyl 5-(2,2,2-trichloroethoxycarbonylamino)-3,5-dideoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid]onate(402948-42-9)
• EPA Substance Registry System: methyl [phenyl 5-(2,2,2-trichloroethoxycarbonylamino)-3,5-dideoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid]onate(402948-42-9)

Safety Data

• Hazardous Substances Data: 402948-42-9(Hazardous Substances Data)

Upstream product

• 66065-85-8 succinimidyl 2,2,2-trichloroethyl carbonate 
• 118977-25-6 methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycerol-β-D-galactonon-2-ulopyranoside)onate 
• 367922-37-0 (2R,4S,5R,6R)-5-Amino-4-hydroxy-2-phenylsulfanyl-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 

Relevant articles and documents

Synthetic study of α(2,8) oligosialoside using N-Troc sialyl N-phenyltrifluoroimidate

An effective approach for the synthesis of oligo-α(2,8) sialosides using N-Troc sialyl donors is described. Glycosylation of N-Troc sialoside with N-Troc sialyl N-phenyltrifluoroimidate and phosphites smoothly proceeded to provide α(2,8) disialosides in g

One-pot synthesis of sialo-containing glycosyl amino acids by use of an N-trichloroethoxycarbonyl-β-thiophenyl sialoside

We describe an efficient synthesis of 2,6- and 2,3-sialyl T antigens linked to serine in a one-pot glycosylation. We first investigated the glycosidation of thiosialosides by varying the N-protecting group. Modification of the C-5 amino group of β-thiosialosides into the N-9-fluorenylmethoxycarbonyl, N-2,2,2-trichloroethoxycarbonyl (N-Troc), and N-trichloroacetyl derivatives enhanced the reactivity of these compounds towards glycosidation. Addition of a minimum amount of 3 A molecular sieves was also effective in improving the yield of α-linked sialosides. Next, we conducted one-pot syntheses of the glycosyl amino acids by using the N-Troc sialyl donor. The N-Troc derivative can be converted into the N-acetyl derivative without racemization of the amino acids. Branched-type one-pot glycosylation, initiated by regioselective glycosylation of the 3,6-dihydroxy galactoside with the N-Troc-β-thiophenyl sialoside, provided the protected 2,6-sialyl T antigen in good yield. Linear-type one-pot glycosylation, initiated by chemoselective glycosylation of galactosyl fluoride with the N-Troc-β-thiophenyl sialoside, afforded the protected 2,3-sialyl T antigen in excellent yield. Both protected glycosyl amino acids were converted into the fully deprotected 2,6- and 2,3-sialyl T antigens linked to serine in good yields.

Synthesis of a sialic acid dimer derivative, 2′α-O-benzyl Neu5Ac-α-(2→5)Neu5Gc

The preparation of a disaccharide 2, Neu5Ac-α-(2→5)Neu5Gc having a α-benzyl protecting group at the reducing end, by the coupling of the easily accessible building units 4 and 5 is described. Subsequent deprotection of the coupling adduct led to the isolation of the target compound 2 in high yield.