Octitols

Page 35, line 3 from bottom. For D-Manno-L-wiawno-octitol read Manno-marmo-octitol since the structure is meso. 

Another proof of the configuration of D-mannitol and also of D-manno-n-manno-octitol (XVI), which is likewise dependent on the experimental proof of the equivalent symmetry of D-mannitol is the following. D-Mannose has been converted, by successive cyanohydrin syntheses, first to a mannoheptose and then to a mannooctose which on reduction yielded a mannooctitol whose octaacetyl derivative is optically inactive. (It was not possible to examine the octitol itself because of its very low solubility in water.)87 The meso character of the octaacetate shows that the mannooctitol must possess a meso configuration, with a plane of symmetry between carbon atoms 4 and 5. To write its formula, the hydroxyl at carbon atom 7 is placed on the... 

The same scheme may be extended to the octoses, e.g., in the correlation of D-manno-L-manno-octose (whose configuration is proved by its reduction to an optically inactive meso octitol)27 and the L-rhamno-... 

D-Galaheptose, origin of name, III, 12 D-Gala-LrffaZa-octaric acid, I, 29 L-Gala-D-ffaZa-octaric acid, I, 29 D-Gala-L-goZo-octitol, and octaacetate, I, 35... 

D-Gluco-D-j/ola-decose, I, 29 d-G1u co- L-jala-octitol, I, 20, 22 and octaacetate, I, 35 D-Gluco-L-0o2a-octose, I, 20, 22 Gluco-ffulo-heptitol, and heptaacetate, I, 9, 34, 35... 

D-Gluco-L-talo-octitol, I, 22 and octaacetate, I, 35 D-Gluco-L-tolo-octose, I, 22 [Pg.363]

D-Mannooctitol HOHjC C-C-C-C-C-C - CHjOH Manno-manTW-octitol... 

Both the D-(o,o,o,o)- and D-(a,a,a,i8)-glucodeconic lactones of Philippe were strongly levorotatory (see p. 18) since their y-carbon atom is the carbon atom 2 of the antecedent o-a-glucooctose the levorotations indicated that the full configurations of this octose and its octitol are the following ... 

Step 6. The optical activity of the octitol requires that this side be the upper. 

The proof is now complete and the full configuration has become the one that is shown on p. 22 for this octitol. The configurations of d-glucose and natural galactose follow obviously, and it is seen that the symbol d is necessary for this form of galactose. 

D-Manno-i manreo-octitol 262° meso 100 pts. water 166° meso 25 pts. 95% ale. ... 

The octitol derivative 184 has been prepared via BF3 etherate-promoted addition of (R)-y-OTBS allylic stannane (i )-181 to enal 180 derived from L-serine (O Scheme 69) [319]. This leads to a single i yw-adduct 182 which is converted to the silyl ether 183. This compound... 

Further NMR studies were performed of molybdate(VI) and tungstate(VI) complexes with the hexitols 40 and 41, the heptitols 42 6, and the octitols 47 and 48. 

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