1030385-81-9

Basic information

• Product Name: 1-O-(3β-acetoxy-lup-20(29)-ene-28-oyl)-2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl
• Synonyms: 1-O-(3β-acetoxy-lup-20(29)-ene-28-oyl)-2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl
• CAS NO: 1030385-81-9
• Molecular Weight: 1077.32
• Mol File: 1030385-81-9.mol

Chemical Properties

• CAS DataBase Reference: 1-O-(3β-acetoxy-lup-20(29)-ene-28-oyl)-2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl(CAS DataBase Reference)
• NIST Chemistry Reference: 1-O-(3β-acetoxy-lup-20(29)-ene-28-oyl)-2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl(1030385-81-9)
• EPA Substance Registry System: 1-O-(3β-acetoxy-lup-20(29)-ene-28-oyl)-2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl(1030385-81-9)

Safety Data

• Hazardous Substances Data: 1030385-81-9(Hazardous Substances Data)

Upstream product

• 10376-50-8 3-O-acetylbetulinic acid 
• 183901-63-5 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate 

Relevant articles and documents

SACCHARIDE LUPANE DERIVATIVES, THEIR USE AND PHARMACEUTICAL COMPOSITIONS CONTAINING THESE DERIVATIVES

This invention relates to saccharide lupane derivatives of general formula (I), wherein R denotes substituent independently selected from the group comprising hydrogen, hydroxy, amino, mercapto, alkyloxy, alkyl and saccharide group, R′ denotes substituent independently selected from the group comprising hydrogen, hydroxy, alkyl, carboxyl, acyl and saccharide group, wherein at least one of R and R′ contains a saccharide group. A further object relates to these compounds for use as medicaments and growth regulators. This invention further includes pharmaceutical compositions containing said derivatives.

Synthesis of lupane-type saponins bearing mannosyl and 3,6-branched trimannosyl residues and their evaluation as anticancer agents

The saponins modified with mono- or trimannosyl residues can provide a convenient means of delivering drugs to certain human cells via interactions with mannose receptors. In the study reported therein, we developed a convenient approach for the synthesis of 3-O-mannoside and branched trimannoside derivatives of the saponin lupeol and of C-28 acyl esters of 3-O-acetyl-betulinic acid bearing the same mannosyl entities. Lupeol and 3-O-acetyl-betulinic acid were mannosylated with tetra-O-benzoyl- or tetra-O-acetyl-α-d-mannopyranosyl trichloroacetimidates. De-esterification followed by regioselective dimannosylation of the unprotected monosaccharide derivatives with 2 equiv of tetra-O-benzoyl-α-d-mannopyranosyl trichloroacetimidate selectively yielded O-3,O-6-linked trimannosides. The cytotoxic activity of selected lupane-type saponins (derivatives of lupeol, betulinic acid, and betulin) toward normal human fibroblasts and various cancer cell lines was also compared.