192929-31-0Relevant academic research and scientific papers
Synthesis of 2-deoxy-2-C-alkyl glycal and glycopyranosides from 2-hydroxy glycal ester
Daskhan, Gour Chand,Jayaraman, Narayanaswamy
experimental part, p. 2185 - 2191 (2012/06/01)
A method to convert 2-hydroxy glycal ester to the corresponding 2-deoxy-2-C-alkyl glycal in a facile manner, through key reactions including (i) C-allylation at C-1, (ii) Wittig reaction, and (iii) Cope rearrangement of a 1,5-diene derivative, is reported. The α-anomer of the 1,5-diene derivative underwent Cope rearrangement to afford 2-deoxy-2-C-glycal derivative, whereas the β-anomer was found to be unreactive. Employing this sequence, 3,4,6-tri-O-benzyl-2-O-acetyl-1,5-anhydro-d-arabino-hex-1-enitol was transformed to 3,4,6-tri-O-benzyl-2-deoxy-2-C-alkyl-1,5-anhydro-d-arabino-hex-1-enitol. 2-Deoxy-2-C-alkyl glycal derivative is a suitable glycosyl donor to prepare 2-deoxy-2-C-alkyl glycosides, mediated through haloglycosylation and a subsequent dehalogenation. A number of 2-deoxy-2-C-alkyl glycosides, with both glycosyl and nonglycosyl moieties at the reducing end, are thus prepared from the glycal.
Synthesis of fused pyran-carbahexopyranoses as glycosidase inhibitors
Doddi, Venkata Ramana,Kancharla, Pavan K.,Reddy, Y. Suman,Kumar, Amit,Vankar, Yashwant D.
body text, p. 606 - 612 (2009/05/11)
Synthesis of polyhydroxylated oxabicyclo[4,4,0]decanes, which constitute a new family of annulated carbasugars, has been accomplished in a stereoselective manner by employing readily available 1,2-anhydro-3,4,6-tri-O-benzyl-α-d-glycopyranoses.
Cytotoxic effects of C-glycosides in HOS and HeLa cell lines
Sanhueza, Carlos A.,Mayato, Carlos,Machin, Ruben P.,Padron, Jose M.,Dorta, Rosa L.,Vazquez, Jesus T.
, p. 3676 - 3681 (2008/02/05)
Fifty-two C-glycosides were synthesized and their in-vitro antiproliferative activity screened against human cervical carcinoma (HeLa) and osteosarcoma (HOS) cell lines. Nine of them had growth inhibitions (GI50 values) below 10 μM, the C-gluco
Antiproliferation and apoptosis induced by C-glycosides in human leukemia cancer cells
Sanhueza, Carlos A.,Mayato, Carlos,Garcia-Chicano, Maria,Diaz-Penate, Raquel,Dorta, Rosa L.,Vazquez, Jesus T.
, p. 4223 - 4227 (2007/10/03)
A large series of alkyl C-glycosides was synthesized from d-glucal or d-galactal. These compounds were screened against the human promyelocytic leukemia cell line (HL60), showing significant activity and apoptosis. Up to 13 C-glucopyranosides, but no C-ga
Multifunctionalized α,β-cyclopentenones from C-2 and C-4-ulopyranosyl compounds: A stereospecific rearrangement initiated by base
Zou,Wang,Lacroix,Wu,Jennings
, p. 223 - 231 (2007/10/03)
Base treatment of O-benzyl protected C-2- or C-4-ulopyranosyl compounds (4α, 4β, and 11) by either 10% Et3N or 1% K2CO3 in MeOH initiated a β elimination to afford α,β-unsaturated C-ulopyranosyl compounds (5α, 5β, and 12), which further rearranged in a stereocontrolled manner to multifunctionalized α,β-cyclopentenones (6 and 14) in 70-80% yield. Both C-α- and C-β-2-ulosides (5α and 5β) produced the same cyclopentenone 6, indicating that a 1,2-enolate is formed prior to the cleavage of the C-5-O bond. Because 6 is racemic, it was probably formed by the intramolecular cycloaldolization of two equally populated enantiomeric intermediates. When treated with 90% Et3N in MeOH, 5α yielded almost exclusively 15 (isomer of 6), which was formed by a migration of the double bond in 5α during the previously described rearrangement. Thus either 6 or 15 was the major product, depending on the base used.
