By Claude S. Hudson, etc.
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Extra resources for Advances in Carbohydrate Chemistry, Vol. 5
63 55 4 Abs. EtOH Reflux 1 hr. 78 55 10 8 Abs. EtOH Reflux 2 hrs. Abs. EtOH Reflux 4 hrs. 59 56 U 28 6 - 6 6 - - - 95 % EtOH Reflux 1 hr. 95% EtOH Reflux 1 hr. - I P 81 78 85 59 17 Aq. EtOH Reflux 2 hrs. 95 59 28 80% EtOH Reflux 2 hrs. 47 60 - s 57, 58 50 50 Reflux 2 hrs. - g 47 Aq. 7 6o - 4 ! 3w M I5 N c4 00 111. Ganhydro-wglucitol tetraacetate l-Thiocyan~l-desoxy-2,4: 3,5dimethyiene-~,bxycxylitol to l-desoxy-2,4: 3, 5dimethylene-~,~-xyfitol -Continued)- - TEE SUGAR SERIES Rotw of Ni D Temp. compoulu Yield Refer% m - 3 2 ?
70, 1751 (1948). (27) W. Z. Hassid, M. Doudoroff, H. A. Barker and W. H. Dore, J. Am. Chem. , 68, 1465 (1946). (28) M. Doudoroff, W. Z. Haasid and H. A. Barker, J. Bid. , 168,733 (1947). (29) W. Z. Hassid, M. Doudoroff, H. A. Barker and W. H. Dore, J . Am. Chem. , 67, 1394 (1945). (30) W. Z. Hassid, M. Doudoroff, A. L. Potter and H. A. Barker, J. Am. Chem. , 70, 306 (1948). 36 W. Z. HASSID AND M. DOUDOROFF in the rate of utilization of the D-glucose-l-phosphate is observed. However, when the same amount of L-arabinose is added to a similar mixture, with the exception that the D-fructose concentration is so selected as to give a maximum rate of sucrose formation, the total rate of D-glucose-lphosphate utilization is decreased.
J . Am. Chem. , 69, 706 (1947). 24 HEWITT G. , AND NELBON K. RICHTMYER bHIOAc LXXXI bHpOAc I1 7 . 70 The final step, namely, the reduction of the two 6-iodo-6-desoxy-D-glucose tetraacetates (LXXXII) in high yield, proved to be particularly difficult and a variety of methods were studied. Highest yields were obtained when LXXXII was allowed to react with thiourea to form the S-substituted isothiuronium iodide (LXXXIII) which was then desulfurized with Raney nickel. In actual practice the 6-iodo derivative was refluxed briefly in amyl alcohol with thiourea and &EL- hHasCNHri 4H LXXXIII AH' LXXXIV then desulfurized directly; under these conditions the yields of bdesoxy compounds from the a- and 8-isomers were 55 and 70% respectively.