Glucose compounds

Start with the easy ones Glucose [compound (iv) ] should be familiar to you and it is one of only two substrates in glycolysis which is not phosphorylated the other one being pyruvate [compound (i)]. 

First compare each Haworth projection with that of 0-D-glucose. Compound (a) differs in configuration at carbon 3. Compound (b) differs in configuration at carbons 2 and 3. 

Fluorodeoxy glucose compounds and C labeled sugars were purchased through Sigma chemical company. Fluorodeoxy galactose compounds were a generous gift from Dr. Stephen Withers, University of British Columbia. 

Under basic conditions, the thiourethano group also reacted by displacement by the nitrogen atom. The D-glucose compound (212), on reaction with methanolic sodium methoxide at room temperature, gave ... 

The anomeric selectivity observed in the synthesis of glucosides (including disaccharides) by reaction of 1-0-metallated 2,3, -tri- -benzyl-D-glucose compounds with alkyl triflates is dependent upon the substituent at 0-6. Good g-selectivity was observed for the 6-benzyl ether, while for the monomethoxytrltyl derivatives, the a 6 ratio was dependent upon the triflate employed.The 0-xylosyl serine derivative (9) has been made using the trlchloro-... 

The amino-oxazoline 37, and hence the trehalose inhibitor trehazolin 38, have been prepared by nitrone addition to a hexenal derivative obtained from D-glucose. Compound 38 has also been synthesized together with analogues 39 (both epimers) from myo-inositol to establish the correct structures of trehazolin and its epimer trehalostatin. >102... 

Nishira H, Joslyn M A 1968 The galloyl glucose compounds in green carob pods (Ceratonia sili-qua). Phytochemistry 7 2147-2156... 

A study of the stability of compounds derived from D-glucose and D-fructose with boric acid or phenylboronic acid has found that the stability constants for the fructose compounds are much greater than those for the glucose compounds. The synthesis of crystalline 3-0-acetyl-2,4-0-phenylboranediyl- -D-ribopyranosyl bromide in a two pot process from D-ribose has been described along with some of its selective glycosylation reactions. Ethyl (dimethoxy)borane has been used in the synthesis of anomerically pure furanosides from the free sugars. Thus methyl 2,3-0-ethylboranediyl-tt-D-lyxofuranoside was prepared and then de-esterified under essentially neutral conditions to the glycoside in 80%... 

Section) imposes greater stereoelectronic control which leads to greater axial selectivity. Two reports have appeared on the preparation of etoposide (130) which is a clinical anticancer substance. Both use 1-thio-D-glucose compounds, but the first employs a bromine atom and the second a coordinated hydroxy group for leaving purposes. A 45% 3deld is claimed in the latter in the former report sulfoxide and sulfone analogues were described. 

Nishira, H., and M. A. Joslyn The Galloyl Glucose Compounds in Green Carob Pods (Ceratonia Siliqua). Phytochemistry 7, 2147 (1968). 

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