Of higher carbon sugars

Such aldolase-catalyzed bidirectional chain elongation ( tandem aldolization) of simple, readily available dialdehydes has been developed into an efficient method for the generation of higher carbon sugars (e.g. (87)/(89)) by simple one-pot operations (Figure 10.32) [126,156]. The choice offuranoid (87) or pyranoid (89) nature of the products can be determined by a suitable hydroxyl substitution pattern in a corresponding cycloolefinic precursor (86) versus (88)). The overall specific substitution... 

C. S. Hudson, The Fischer Cyanohydrin Synthesis and the Configurations of Higher-carbon Sugars and... 

Sugar allyltins (mentioned already in 2.2.3.) were used for the preparation of higher carbon sugars. This may be illustrated by reaction of the furano-side 99 with di-O-isopropylidene-D-arabinose performed under high pressure, which provided compound 100 (Fig. 33).43,48... 

O. Achmatowicz, An approach to the synthesis of higher-carbon sugars, in Organic Synthesis, Today and Tomorrow, B. M. Trost and C. R. Hutchinson, eds., Pergamon Press, Oxford, 1981, p. 307. 

How, M. J., Brimacombe, J. S., and Stacey, M., The Pneumococcal Polysaccharides, 19, 303-357 Hudson, C. S., Apiose and the Glycosides of the Parsley Plant, 4, 57-74 Hudson, C. S., The Fischer Cyanohydrin Synthesis and the Configurations of Higher-carbon Sugars and Alcohols,... 

In 1946, he was appointed Assistant Professor of Chemistry at the University of San Francisco, California. Even with a heavy teaching load, he found time to do research which was conducted under something less than desirable conditions. In order to get to his laboratory from his office, he had to push his desk into a comer, lift a trap door, and climb down a ladder to the laboratory. Despite these handicaps, he published five papers in the year that he held the post. In 1947, Karabinos returned to St. Procopius College, Lisle, Illinois, but this time as Professor and Head of the Chemistry Department, a position that he held from 1947-1949. In 1949, he became a Chemical Foundation Research Associate with C. S. Hudson, at the (then) National Institute of Health, Bethesda, Maryland. There, Karabinos was involved in the preparation of higher-carbon sugars by the addition of hydrogen cyanide. Often, one of his roles in this effort was to obtain, at the factory, commercially produced liquid hydrogen cyanide in Dewar flasks... 

THE FISCHER CYANOHYDRIN SYNTHESIS AND THE CONFIGURATIONS OF HIGHER-CARBON SUGARS AND ALCOHOLS... 

XIII. Nomenclature of Higher-carbon Sugars from Hexoses. 28... 

Marco Contelles, J, de Opazo, E, Arroyo, N, Synthesis of higher-carbon sugars by addition of organometalUc reagents to aldehydes or lactols derived from carbohydrates. Tetrahedron, 57, 4729-4739, 2001. 

For a review, see Jarosz, S, Synthesis of higher carbon sugars via coupling of simple monosaccharides — Wittig, Homer-Emmons, and related methods, J. Carbohydr. Chem., 20, 93-107, 2001. 

Jarosz, S, Mach, M, Phosphonate versus phosphorane method in the synthesis of higher carbon sugars. Preparation of D-erythro-L-manno-D-gluco-dodecitol, J. Chem. Soc., Perkin. Trans. 1, 3943-3948, 1998. 

Brimacombe methodology of the synthesis of higher carbon sugars... 

The synthesis was initiated from the easily available unsaturated aldehyde 60, which reacted with tributyltin cuprate affording a 1,4-adduct (as a mixture of stereoisomers), trapped as trimethylsilyl ethers 61a and 61b. Reaction of these reactive species with synthon 62 afforded the unsaturated precursors of higher carbon sugars 63 and 64. 

The synthesis of higher carbon sugars by an Achmatowicz approach was realized by Indian scientists [96]. This example should have been presented in O Sect. 2 (describing general methods) however, since it illustrates a concise approach to the synthesis of unsaturated sugars using different methods it is included here. 

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