Carbohydrate Research p. 291 - 304 (1988)
Update date:2022-08-05
Topics:
Baer, Hans H.
Williams, Ursula
Radatus, Bruno
Chemical reactions to open the cyclopropane ring in (1R)-1,2-dideoxy-3,4:5,6-di-O-isopropylidene-1,2-C-methylene-1-nitro-D-mannitol (1) were investigated.Catalytic hydrogenation over Pd-C produced the corresponding 1-amino compound, isolated as its N-acetyl derivative, but failed to cleave the ring.However, ring opening succeeded by nucleophilic addition of sodium thiophenoxide to 1, giving 1,2-dideoxy-3,4:5,6-di-O-isopropylidene-1-nitro-2-C-(phenylthio)methyl-D-mannitol.The latter reacted further with thiophenoxide to furnish phenyl 2-deoxy-3,4:5,6-di-O-isopropylidene-2-C-(phenylthio)methyl-D-mannothiohydroximate.Raney nickel converted both of these thio sugar derivatives into the same product, namely, 1-acetamido-1,2-dideoxy-3,4:5,6-di-O-isopropylidene-2-C-methyl-D-mannitol.The use of these transformations for the design of stereospecific syntheses of chiral isoalkyl structures is proposed.
View Morewebsite:http://www.finerchem.com
Contact:+86-531-88989536
Address:New Material Industry Park, Jinan Ciyt, China
Changzhou LanXu Chemical Co.,ltd.(expird)
Contact:86-0519-86330911,13656129734,15261186386
Address:Room 524, Depart.Chemical, Changzhou Science and Eductaion town, Jiangsu, China;Factory: Haian Fine Chemical Industry Park,Nantong,Jiangsu,China
Suzhou Chiral Pharmaceuticals Co., Ltd.
Contact:86-0512-63197058
Address:Building A, No. 2358, Chang'an Road, Wujiang Science Park
Lonzeal Pharmaceuticals Co., Ltd.
website:http://www.lonzeal.com
Contact:+86-13381011962
Address:RM 801, Yue MOMA, No. 26 Anningzhuang Rd. Haidian District, Beijing, China
Contact:+86-22-26358246
Address:601-4-20, Fujiayuan, Tiantai Road, Hebei District, Tianjin, China
Doi:10.1134/S1070363208060236
(2008)Doi:10.1016/S0040-4039(00)80169-0
(1988)Doi:10.1039/c39880000232
(1988)Doi:10.1016/j.tetlet.2009.04.010
(2009)Doi:10.1016/j.jorganchem.2009.02.008
(2009)Doi:10.1021/om900168y
(2009)