Threitols

The other tetritols were formerly called d-and /-erythritol, but have been renamed L-and D-threitol respectively. A racemic form can also be prepared,... 

Fig. 1. Stmctures of the tetritols (a) erythritol, (b) D-threitol, and (c) L-threitol and the pentitols (d) ribitol, (e) D-arabinitol, (f) L-arabinitol, and (g) xyhtol.

The initial investigation focused on the use of threitol-derived auxiliaries with various substituent groups on the dioxolane ring (Table 3.3). However, it became evident that the oxygen atoms in the substituents had a detrimental effect on selectivity. Comparison of the diastereoselectivities for the ketals 69-71, which contain Lewis basic sites in the substituents at the 1 and 2 positions, with those from simpler diol derived ketals 72-74 demonstrates the conflicting effects of numerous coordination sites. The simpler, diol-derived ketals provide superior results compared to the threitol derived ketals. The highest diastereoselectivity is observed in the case of the 1,2-diphenyl ethane-1,2-diol derived ketal 74. 

Amino-sugars and Related Compounds. Part VII. 2-Amino-2-deoxy-1,3,4,5-tetra-O-methyl-D-glucitol, 2-Amino-2-deoxy-L-threitol and Certain Derivatives Thereof, A. B. Foster, D. Horton,... 

Products were analyzed via Waters Model 515 HPLC Pump fitted with a Waters model 2410 refractive index detector. Separations was performed via an Aminex HP-87H 300mm column at 65°C using 0.005M H2SO4 as the mobile phase. Compounds calibrated for this work included xylitol, arabitol, erythritol, threitol, PG, EG, glycerol, lactate, 1-propanol, 2-propanol, ethanol, methanol, and the butanetriol isomers. Any compounds not visible by RID were not quantified in this work. 

Fig. 19. A series of 2nd-generation dendrimers with chiral spacers derived from (R,R)- or (S,S)-tartaric acid. Note that the (R,R)-threitol-acetonide building blocks in 49 - 51 are derived from (S,S)-tartaric acid, and vice versa [78-80]...

The molar rotation of the dendrimers 49-51 is proportional to the excess of (R,R)- or (S,S)-threitol units. This means that the chiroptical effects of threitol building blocks of opposite chirality cancel out each other. For the homo dendrimers an average positive molar optical rotation value of 146 for each (i, k)-threitol unit was calculated whereas a value of -185 resulted for each... 

Scheme 4-21 shows the preparation of L-threitol and L-erythritol.38 Epoxy alcohols (2J ,3iS)-61 and (2S,3/ )-61. generated by asymmetric epoxidation, are exposed to sodium benzenethiolate and sodium hydroxide in a protonic solvent to undergo base-catalyzed rearrangement, yielding the threo-diol 62 and erythro-diol 63, which can then be converted to the corresponding tetraacetate of l-threitol 67 and L-erythritol 69 through subsequent transformations. 

A Z>2-symmetric chiral /ra/7,v-dioxoruthenium( VI) porphyrin, [RuVI(L1)02], bifa-cially encumbered by four threitol units can effect enantioselective epoxidation of (fs)- 3-methylstyrene in up to 70% ee. For the asymmetric styrene oxidation, a lower enantioselectivity of 40 % ee was obtained (c.f. 62 % ee, see Table 6.3) when... 

Anderson, L. E., T.-C. L. Ng, and K-E. Y. Park. Inactivation of pea leaf diloro plastic and cytoplasmic glucose 6-phosphate dehydrogenases by light and dithio-threitol. Plant Physiol. 53 835-839, 1974. 

Among the 1,4-di-O-substituted-L-threitol derivatives (Figure 14a) the one that has found most use in chiral crown ether synthesis is the 1,4-dibenzyl ether. Not only has it provided (88, 106, 107) a ready entry into the chiral tetrasub-stituted 18-crown-6 derivatives ll-31 to ll-34, but it has also proved to be a usehil chiral precursor for the preparation of chiral disubstituted 9-crown-3 (107), 12-crown-4 (108), 15-crown-5 (108), and 18-crown-6 (109) derivatives l-57, l-58, l-59, and l-60, respectively. In the preparation of l-S8 the base-promoted cyclization with triethylene glycol ditosylate is best carried out (108) with a... 

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