Journal of Organic Chemistry p. 5348 - 5353 (1986)
Update date:2022-07-29
Topics:
Warm, Aleksander
Vogel, Pierre
The ''naked sugars'' are optically pure synthetic intermediates.Their advantage compared with natural sugars is that they possess a number of unsubstituted carbon atoms that can be substituted stereospecifically through direct procedures. (1S,2R,4S)-2-<(-)-Camphanoyloxy>-7-oxabicyclo<2.2.1>hept-5-ene-2-carbonitrile ((+)-1) is an example of a ''nuked sugar''.Electrophilic reagents add to the C(5), C(6) double bond, giving the corresponding adducts where the electrophile substitutes the exo position of C(6) and the nucleophile the endo position at C(5).This principle was used to prepare (1R,4R,5R)-5-endo-chloro-7-oxa-2-bicyclo<2.2.1>heptanone (13), which was monomethylated stereoselectively in the exo position at C(3), giving (+)-(1R,3S,4R,5R)-5-endo-chloro-3-exo-methyl-7-oxa-2-bicyclo<2.2.1>heptanone (14).The latter was transformed stereospecifically indo L-daunosamine (3-amino-2,3,6-trideoxy-L-lyxo-hexose).The (-)-camphanic acid used to engender asymmetry was recovered at an early stage of the synthesis.
View MoreHangzhou Hysen Pharma co.,Ltd.
website:http://www.hysenpharma.cn/
Contact:0086-571-88298791
Address:#701,Gudun Road Hangzhou
Contact:+86-531-58668191 58668193 58668196 58661173
Address:No 55,Beixiaoxinzhuang West Street,Jinan City, Shandong Province
Feis International Trade Co,. Ltd
Contact:13961823444-18235944442
Address:Wuxi jiangsu
Nantong Advance Chemical Co., Ltd
Contact:86-13818730908
Address:Fine Chemical Industry Garden,Beixin Town,Qidong
Shanghai Gsyn Chemical Co.,Ltd.
Contact:86-021-67158290
Address:86-021-67158291
Doi:10.1002/anie.200603394
(2007)Doi:10.1021/ja804078v
(2008)Doi:10.1016/S0040-4020(01)87569-4
(1986)Doi:10.1021/jm8002153
(2008)Doi:10.1016/j.tetasy.2008.07.003
(2008)Doi:10.1039/c7cc06881f
(2017)