Branched-chain sugar nucleosides

Synthesis of 6-Chloro-9-(6 -deoxy-3 -C-methyl-2, 3, 4 -tri-0-methyl-/3-D-allopyrano-syl)purine A Branched-chain Sugar Nucleoside, G. B. Howarth, W. A. Szarek, and J. 

Rosenthal, A, Sprinzl, M, Branched-chain sugar nucleosides. IV. 9-(3-deoxy-3-C- hydroxymethyl -P(and a)-D-allofuranosyl and ribofuranosyljadenine. Can. J. Chem., Al, 4477-4481, 1969. Rosenthal, A, Catsoulacos, P, Synthesis of branched-chain sugars by the Wittig reaction. Can. J. Chem., 46, 2868-2872, 1968. 

Rosenthal, A, Nguyen, L, Branched-chain sugar nucleosides I. 9-(3-deoxy-3-C-(2 -hydroxyethyl)- 3-D-allofuranosyl)-adenine and 9-(3-deoxy-3-C-(2 -hydroxyethyl)- 3-D-ribofuranosyl)-adenine, J. Org. Chem., 34, 1029-1034, 1969. 

The branched-chain sugar nucleosides (54) and (55) have been prepared by conventional methods from the corresponding sugars, whose synthesis is referred to in Chapter 13. The branched-chain uridine derivatives show in vitro activity against cultured L1210 cells. ... 

Branched-chain sugar nucleosides of apiose have been synthesized from the derivatives (65) and (66) and the TMS derivatives of uracil, thymine, 5-bromo-uracil, or 5-iodo-uracil using tin(iv) chloride catalysis. The synthesis of... 

Deoxy-branched chain sugars are also referred to as precursors for alkaloid and polyketide synthesis in Chapter 24, and branched-chain sugar nucleosides are mentioned in Chapter 20. 

M. Nomura, S. Shuto, M. Tanaka, T. Sasaki, S. Mori, S. Shigeta, and A. Matsuda, Nucleosides and Nucleotides. 185. Synthesis and biological activities of 4 -a-C-branched-chain sugar pyrimidine nucleosides, J. Med. Chem., 42 (1999) 2901-2908. 

A. Rosenthal and S. N. Mikhailov, Branched-chain sugars. Modifications in the reaction of l,2 5,6-di-0-isopropylidene-oi-D-ribo-hexofuranos-3-ulose with Giignard and oiganolithium reagents, J. Carbohydr. Nucleosides Nucleotides 6 237 (1979). 

The reaction of 2-formylglycals with malononitrile afforded push-pull butadienes with a sugar moiety. The treatment of these branched-chain sugars with ammonia yielded nicotinonitrile acyclo-C-nucleosides. Furthermore, a one-step ring transformation of 2(3)-formylglycals with Af-aryl-acetoacetanilides gave pyridone acyclo-C-nucleosides [140-142]. 

The preparation of the branched-chain sugar found in the naturally occurring nucleoside antibiotic amipurimycin is depicted in Scheme 1. The synthesis involved deoxygenation at C-4 of a 3-ulose derivative with triphenyphosphine-iodine-imidazole in the first step. ... 

---