5-Deoxy analogue

A series of 9-deoxy analogues was prepared from 13-acetyl-9(/f)-OH-baccatin III (44) by an Abbott Lab group. They found that the 9-deoxypaclitaxel 52a... 

Whereas 2-deoxy-fortimicin A has full antibacterial activity (205), and the 2-deoxy-3-demethoxy- derivative is even more active than fortimicin A (236), the 2,5-dideoxy derivative has poor activity, as do the 2-deoxy-2-chloro and the 2,5-dideoxy-4,5-dehydro derivatives. The 2-amino-3-0-demethyl-2-deoxy analogue has quite good activity (229). 

Deoxy-sugars. Part XV. D-Gaiactose-3 and -6 Phosphoric Acids and their 2-Deoxy-analogues, A. B. Foster, W. G. Overend, and M. Stacey, J. Chem. Soc., (1951) 980-987. 

By analogy with the conversion of uridine 1 into cytidines 6, the conventional amination of inosine 235a, guanosine 235b, or xanthosine 235c and their 2 -deoxy analogues to the adenosines 237 requires ... 

P5N has two isozymes, P5N-I (pyrimidine nucleotidase) and P5N-II (deoxyri-bonucleotidase) (H6, P2). P5N-I is active principally with pyrimidine substrates at an optimal neutral pH P5N-II activity occurs with both purine and pyrimidine substrates and was maximal with deoxy analogues at an acidic pH optimum. This enzyme was partially purified from human red blood cells and had a molecular weight of 28,000 (T19). The primary structures of both isozymes have not been... 

The role of the kinetic anomeric effect was demonstrated by the difference in diastereoselectivities observed for the addition of LiP03Me2 to IV-glycosylnitrone 51 and to the deoxy analogue 52. In TFIF, the difference in diastereoselectivities corresponds to a value of 1.1 kcal/mol while in CH2CI2 it gives a value of 0.6 kcal/mol. Moreover the deoxy derivative 52 undergoes a slower reaction than its parent glycosylnitrone 51. 

Compound 160 was used as donor for the preparation of methyl 4,6-dideoxy-a-L-/yxo-hexopyranosyl-(l -> 3)-2-acetamido-2-deoxy-a-D-glucopyranoside, the 4 -deoxy analogue of the linkage disaccharide to the galactan chain in mycobacteria.235... 

C. Herve du Penhoat, A. Imberty, N. Roques, V. Michon, J. Mentech, G. Descotes, and S. Perez, Conformational behaviour of sucrose and its deoxy analogue in water as determined by NMR and molecular modelling, J. Am. Chem. Soc., 113 (1991) 3720-3727. 

Pyranoid compounds such as 252 undergo hydroboration and hydrogenation to give mixtures of D-glucose and L-idose derivatives and their 6-deoxy analogues, respectively, the ratios depending on reaction conditions and on structural details of the substrates. Acid-catalyzed hydrolysis leads to 6-deoxyaldos-5-uloses.6... 

J. Mlynarski and A. Banaszek, A novel chemical synthesis of a 3-deoxy-D-arabino-heptulosonic acid 7-phosphate (DAHP) derivative and its 2-deoxy analogue, Carbohydr. Res., 295 (1996) 69-75. 

Comparison Between the Experimental J Values (Hz) Described by Wu et alP for the Glycosidk Tbrsion of a Series of fi- (8) and a-Linked (10) C-Glycosyl Compounds and Their 2-Deoxy Analogues (9,11), and the Expected J Values (Hz) Given in Table I ... 

Monti s research group very recently described an enantioselective and divergent approach towards certain 3-methyl 4a-carbaaldofuranoses and their 2-deoxy analogues, capitalyzing on a well established chemoenzymatic resolution of racemic cyclopentene precursors [12]. 

Noteworthy, if otherwise elaborated, 107 could diverge into the 6-deoxy-analogue 111, an isomer of the biologically valuable carbafucopyranose. 

Sharma s group has also synthesized guineensine, which is the alkaloid produced by both Piper guineense and P. officinarum.14 The isolation of trans- and cis-(—)-clovamides and their deoxy-analogues from the bark of Dalbergia... 

A new aromatization of ring c has been achieved by treating the 16a, 17a-epox ypregn-8-ene-7,ll,20-trione system (277) with zinc chloride in acetic anhydride.227 The product (278) was accompanied by the diene-trione (279). Use of other acidic reagents, or of the 7-deoxy-analogue of compound (277), failed to give an aromatic product. 

Alternatively, the aromatic ring of an unsubstituted phenylacetate can itself act as a carrier, apparently forming a loose complex with a chlorine atom. 5a-Cholestan-3a-yl phenylacetate with iodobenzene dichloride, irradiated in dichloromethane, gave the A9(U)-olefin in 53% yield, with no detectable A14-isomer.237 The radical-carrier principle has been used to introduce A9(1 -unsaturation in a novel synthesis of cortisone from its 11-deoxy-analogue (Reichstein s S).238... 

Some 2-deoxy-analogues of rubrosterone have been reported.73 The synthesis commenced with a Bamford-Stevens reaction upon 3/3,17/3-diacetoxyandrost-5-en-7-one tosylhydrazone to yield the corresponding 5,7-diene. Successive chromic acid and selenium dioxide oxidation of this diene furnished the 2-deoxyrubrosterones (177 R1 = OAc, R2 = H, R3 = OH, X= 17/3-0Ac,H 5a-H) and (177 R = OAc, R2 = R3 = H, X = 17/3-OAc,H 5a-H) respectively. Alkaline hydrolysis of the latter derivative afforded an A-homo-B-nor-steroid (178). The rubrosterone (177 R1 = R2 = R3 = OH, X = O 5/3-H), which possesses antidiabetic activity, has been prepared by oxidative degradation of the cholestene (179), itself obtained from ecdy-sterone.74... 

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