132377-68-5Relevant academic research and scientific papers
Synthesis of taxoids II. Synthesis and antitumor activity of water-soluble taxoids
Harada, Naoyuki,Ozaki, Kunihiko,Yamaguchi, Tetsuo,Arakawa, Hiroaki,Ando, Akira,Oda, Kouji,Nakanishi, Noriyuki,Ohashi, Motoaki,Hashiyama, Tomiki,Tsujihara, Kenji
, p. 241 - 258 (2007/10/03)
Synthesis of novel taxoid water-soluble prodrugs that have 2′-substituted amino acid derivatives with spacer is described. Enantioselective synthesis of the C-13 side chains proceeded through the asymmetric dihydroxylation. Several compounds had good solubility in saline and showed potent antitumor activity against B16 melanoma in mice.
Selective Transformations of threo-2,3-Dihydroxy Esters
Fleming, Paul R.,Sharpless, K. Barry
, p. 2869 - 2875 (2007/10/02)
Two highly regio- and stereoselective transformations of threo-2,3-dihydroxy esters have been developed.In the first reaction, the α-hydroxy group is converted into a sulfonate group (tosylate or nosylate); the α-tosylates and α-nosylates are then subjected to basic conditions (K2CO3/ROH) to give erythro glycidic esters in high yield.The α-nosylates are also suitable electrophiles for azides, giving access to erythro-α-azido-β-hydroxy esters.The second reaction involves conversion of the diol esters to acetoxy bromo esters.The β-subsituent plays a key role in determining the regiochemistry since cases with β-alkyl substituents afford β-acetoxy-α-bromo esters exclusively, whereas a β-phenyl substitutent directs formation of the α-acetoxy-β-bromo ester.The acetoxy bromo esters can subsequently be converted to the threo glycidic esters (via the bromohydrin esters); selective hydrogenolysis of the bromine substituent can also be achieved.
