Sorbopyranose 1.2- 0-isopropylidene-4-0-methyl

In the sorbose series 3-methyl-D-sorbo8e14 has been synthesized, as well as the aforementioned 4-methyl-8 derivative the latter compound was obtained in a series of reactions from D-fructose derivatives through l,2-isopropylidene-3,4-anhydro-D-psicose. In the earlier study8 the configuration of the 4-methyl ketohexose was shown to be that of a D-sorbopyranose by methylation of l,2-isopropylidene-4-methyl-D-sorbose (VI) to the trimethyl derivative (LXV) which was hydrolyzed to 3,4,5-trimethyl-D-sorbose (LXVI). The latter compound, on oxidation, gave derivatives of levorotatory dimethoxysuccinic acid (LXVIII) and xylo-trimethoxyglutaric acid (LXVII). 

Ohle and Just synthesized l,2-0-isopropylidene-4-0-methyl-j8-D-sorbopyranose (99) from l,2-0-isopropylidene-3-0-p-tolylsulfonyl-j8-D-fructopyranose (97) by successive Walden inversions involving 3,4-anhydro-l,2-0-isopropylidene-j3-D-psicopyranose (98) as the intermediate (see Scheme XV). 

Acetyl-l,3,4,5-tetra-0-benz yl-a-L-sorbopyranose, S-60 2-0-Acetyl-l,3,4,5-tetra-0-benz yl-p-L-sorbopyranose, S-60 l-Amino-l-deoxy-2,3 4,6-di-0-isopropylidene-a-L-sorbofuranose, A-334 6-Amino-6-deoxy-2,3-0-isopropylidene-l-0-methyl-a-L-sorbofuranose,... 

Isopropylidene-3,4,5-tri-O -mesyl-a-L-sorbopyranose, S-60 Methyl 5-acetamido-1,3-0-benzylidene-5-deoxy-a-L-sorbopyranoside,... 

P-D-Fructopyranose a-D-sorbopyranose l,2 2,l -dianhydride, F-77 P-D-Fructopyranose a-L-sorbopyranose l,2 2,l -dianhydride, F-78 Isopropyl 3,4,6-tri-O -acetyl-2-bromo-2-deoxy-p-D-glucopyranoside, B-74 Methyl 4,5-anhydro-2,3-0-isopropylidene-D-ribonate, A-691 Methyl 4,7-anhydro-5,6,8-tri-0-benzyl-2,3-dideoxy-2,2,3,3-tetradehydro-D-o/fro -octonoate, M-212 Methyl 4,7-anhydro-5,6,8-tri-0-benzyl-2,3-dideoxy-2,2,3,3-tetradehydro-D-o//o-octonoate, M-212 Methyl 3,5-anhydro-p-D-xylofuranoside, A-728 Methyl 2-bromo-2-deoxy-4,6-0-benzylidene-p-D-glucopyranoside, B-74 Methyl 2-bromo-2-deoxy-p-D-glucopyranoside, B-74 Methyl 3,4,6-tri-O-acetyl-2-bromo-2-deoxy-p-D-glucopyranoside, B-74 v-Octose l,T-Anhydro, 0-17... 

Acetamido-3,5-di-0-acetyI-4-deoxy-l,2-0-isopropylidene-4-C-methyl-p-D-psicopyranose, A-321 4-Acetamido-3,5-di-0-acetyI-4-deoxy-l,2-0-isopropylidene-a-L-sorbopyranose, A-335... 

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