A synthesis of abequose (3,6-Dideoxy-D-xylo-hexose)
The S-methyl 3-O-dithiocarbonates of 1,2:5,6-di-O-isopropylidene-α-D-galactofuranose and ?gulofuranose have been prepared and subsequently reduced with tributylstannane to 3-deoxy-1,2:5,6-di-O-isopropylidene-μ- D-xylo-hexofuranose. Partial hydrolysis of this compound led to the 5,6-diolwhich was deoxygenated at C 6 to form 3,6-dideoxy-1,2-O- isopropylidene-α-D-xylo-hexofuranose, and subsequently abequose on acid hydrolysis. A rationale has been proposed for the variations in hydrolysis of di-O-isopropylidene-α-D-hexofuranoses and derivatives to their 5,6-diols.
1984 ◽
Vol 49
(8)
◽
pp. 1780-1787
◽
Keyword(s):
1991 ◽
Vol 81
(1)
◽
pp. 51-54
◽
Keyword(s):
2017 ◽
Vol 4
(1)
◽
2020 ◽
Vol 26
(3)
◽
pp. 222-233
2012 ◽
Vol 11
(12)
◽
pp. 2313-2318
Keyword(s):