Carbohydrate research p. 125 - 134 (1988)
Update date:2022-08-04
Topics:
Walker
Ehler
Unkefer
2-Deoxy-D-arabino-[6-13C]hexose (10), to be used to test the stability of 2-deoxy-D-arabino-hexose 6-phosphate in brain tissue, was prepared. 2-Deoxy-D-arabino-hexose was labeled at C-6 because of the large difference in chemical shift between C-6 in the free sugar and C-6 in the 6-phosphate. The synthetic scheme resembled that used for the synthesis of D-[6-13C]glucose that involved the removal of C-6 from D-glucose followed by its replacement with 13C. The protected derivative methyl 2-deoxy-alpha-D-arabino-hexofuranoside was prepared, using trifluoroacetic acid in methanol. This was treated with periodate, which cleaves only between C-5 and C-6, to afford an aldehyde which reacted directly with K13CN to give a mixture of the D-arabino and L-xylo nitriles. The enriched nitriles were reduced with hydrogen in the presence of 5% Pd-carbon catalyst to a mixture of 6-aldehydo sugars. These were reduced with NaBH4 to a mixture of the two labeled methyl furanosides. Acid hydrolysis followed by ion-exchange chromatography on AG-50(Ca2+) resin at 65 degrees gave 10 in an overall yield of 16% from K13CN.
View MoreShanghai Forever Biotech Co., Ltd.
Contact:+86-21-69734790
Address:Room 5017/5019、5022、5024 of Technology Innovation Centre, No.1155, Gongyuan East Rd, QingPu District, Shanghai China.
Jiaxing Anrui Material Technology Co., Ltd.
Contact:86-573-82651652 13305832579
Address:Room 407, Technology Building, 1369 Chennan Road, Jiaxing City, Zhejiang, China
Shanghai Zhihua ChemTech Co., Ltd.
Contact:+86-13774313779
Address:Room 817 Suite B 3333 Shenjiang Road
Contact:+44 (0)2036089360-31
Address:Chanceryhouse,Chancery Lan
Xi'an North Information Industry Co., Ltd. Weilv Chemical Department
Contact:+86-29-88156413
Address:Jixiang Road 99 Xi'an Shaanxi Province
Doi:10.1007/BF00962780
(1988)Doi:10.1016/S0040-4039(00)82113-9
(1988)Doi:10.1039/b903375k
(2009)Doi:10.1248/cpb.37.221
(1989)Doi:10.1002/jhet.5570300132
(1993)Doi:10.1039/c8ob00455b
(2018)