Elsevier
Carbohydrate Research
,  volume 155 ,  pages 131-140

Chemical synthesis of the desialylated human Cad-antigenic determinant

Giorgio Catelani 1
, 
Alberto M. Marra 1
, 
Françoise Paquet 2
, 
Pierre Sinaÿ 2
1
 
2
 
Laboratoire de Biochimie Structurale, U.A. 499, U.F.R. de Sciences Fondamentales et Appliquées, B.P. 6759, 45067 Orléans France | 
Publication type: Journal Article
Publication date: 1986-11-01
Elsevier
scimago Q3
wos Q2
SJR: 0.423
CiteScore: 4.0
Impact factor: 2.5
ISSN: 00086215, 1873426X
Organic Chemistry
Biochemistry
General Medicine
Analytical Chemistry
Abstract
Benzyl 2-azido-2-deoxy-beta-D-galactopyranoside was converted into benzyl 2-azido-4,6-O-benzyl-2-deoxy-beta-D-galactopyranoside via benzylidenation, p-methoxybenzylation, acid hydrolysis, benzylation, and selective oxidation. Condensation of 1,2,3,4,6-penta-O-acetyl-beta-D-galactopyranose with benzyl 2-azido-4,6-di-O-benzyl-2-deoxy-beta-D-galactopyranoside in the presence of trimethylsilyl triflate gave crystalline benzyl 2-azido-4,6-di-O-benzyl-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-beta-D-ga lactopyranosyl)-beta-D-galactopyranoside (76%), which was converted into benzyl 2-azido-4,6-di-O-benzyl-2-deoxy-3-O-(2,6-di-O-benzyl-beta-D-galactopy ranosyl)-beta-D-galactopyranoside and condensed with 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl bromide in the presence of silver silicate on alumina and molecular sieve 4 A to give 61% of benzyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-beta-D-galactopyranosyl)-(1----4)- O-(2,6-di- O-benzyl-beta-D-galactopyranosyl)-(1----3)-2-azido-4,6-di-O-benzyl-2-deo xy- beta-D-galactopyranoside. Reduction with sodium borohydride followed by N-acetylation, O-deacetylation, and catalytic hydrogenolysis then gave O-(2-acetamido-2-deoxy-beta-D-galactopyranosyl)-(1----4)-O-beta-D-gal actopyranosyl-(1----3)-2-acetamido-2-deoxy-D-galactopyranose, the desialylated human Cad-antigenic determinant.
Found 
Found 

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GOST Copy
Catelani G. et al. Chemical synthesis of the desialylated human Cad-antigenic determinant // Carbohydrate Research. 1986. Vol. 155. pp. 131-140.
GOST all authors (up to 50) Copy
Catelani G., Marra A. M., Paquet F., Sinaÿ P. Chemical synthesis of the desialylated human Cad-antigenic determinant // Carbohydrate Research. 1986. Vol. 155. pp. 131-140.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/s0008-6215(00)90139-3
UR - https://doi.org/10.1016/s0008-6215(00)90139-3
TI - Chemical synthesis of the desialylated human Cad-antigenic determinant
T2 - Carbohydrate Research
AU - Catelani, Giorgio
AU - Marra, Alberto M.
AU - Paquet, Françoise
AU - Sinaÿ, Pierre
PY - 1986
DA - 1986/11/01
PB - Elsevier
SP - 131-140
VL - 155
PMID - 2431777
SN - 0008-6215
SN - 1873-426X
ER -
BibTex
Cite this
BibTex (up to 50 authors) Copy
@article{1986_Catelani,
author = {Giorgio Catelani and Alberto M. Marra and Françoise Paquet and Pierre Sinaÿ},
title = {Chemical synthesis of the desialylated human Cad-antigenic determinant},
journal = {Carbohydrate Research},
year = {1986},
volume = {155},
publisher = {Elsevier},
month = {nov},
url = {https://doi.org/10.1016/s0008-6215(00)90139-3},
pages = {131--140},
doi = {10.1016/s0008-6215(00)90139-3}
}