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In like fashion methyl 2-methylthio-3-methyl-4,6-benzylidene-a-~-altroside (LXII) was hydrogenolyzed (LXIII). CaHh HAOR IIAOH I HCO- Shortly after the above work appeared, Bolliger and Prinseoreported a similar synthesis leading to a 3- rather than a 2-desoxy derivative. Methyl 2,3-anhydro-4,6-benzylidene-a-~-mannovide (LXIV), upon treatment with sodium thiomethoxide, was converted into methyl 3-methylthio-4,6-benzylidene-a-~-altroside(LXV) which, after desulfurization and rebenzylidenation, gave methyl 3-desoxy-4,6-benzylidene-a-~-mannoside (LXVI).

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. EtOH Reflux 2 hrs. 96 61 r3 d 2 Aq.

Z. , 13, 641 (1938). 8. Most of the unreacted D-xylose waa separated by crystallization, leaving a sirup consisting chiefly of D-xyloketose. 40 W. 2. HASSID AND M. 88 A disaccharide consisting of glucopyranose and xyloketofuranose glycosidically united through positions 1 and 2 of the aldose and ketose monosaccharides, respectively, would possess three adjacent free hydroxyls on carbon atoms 2, 3, and 4 in the glucose residue and two free hydroxyls on carbon atoms 3 and 4 in the xyloketose residue.

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