By Claude S. Hudson, etc.
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Extra resources for Advances in Carbohydrate Chemistry, Vol. 5
56) H. G . , and C. B. Hudson, J . Am. Chem. , 71, 3682 (1949). (5th) R. K. Ness, H. G. , and C. Hudson, J . Am. Chem. , in press. DESULFURIZATION BY RANEY NICKEL 19 Methanolysis of dihydrostreptomycin with subsequent acetylation of the products was found by Brink, Kuehl, Flynn and Folkers6' to give both anomeric forms of methyl pentaacetyldihydrostreptobiosaminide (LVI). Mercaptolysis of either of these anomers, followed by reacetylation, converted them into ethyl pentaacetylthiodihydrostreptobiosaminide (LVII) which was not isolated but immediately desulfurized to the acetylated anhydride LVIII, pentaacetyldihydrodesoxystreptobiosamine.
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 ? 2 Aq. EtOH Reflux 2 hrs. 57 61 15 Aq.
Physiol. , 931, 271 (1935). 31 SYNTHESIS OF SUCROSE Within the last few years some progress has been made toward a better understanding of the mechanisms involved in the biochemical synthesis of sucrose and other disaccharides. It is the purpose of the authors to discuss the presept state of knowledge of this subject. 11. STRUCTURE OF SUCROSE A completely satisfactory constitutional formula for sucrose was long a matter of controversy but there is now general agreement that this problem has been solved.