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Synthesis of showdomycin - ScienceDirect

2,3,4,6-Tetra-O-benzyl-D-glucitol (5) reacts with toluene-p-sulphonyl chloride in pyridine at 60°C to form mainly the furanoid products 2,3,6-tri-O-benzyl-1,4-anhydro-D-glucitol (10) and its 5-toluene-p-sulphonate (11) with loss of the 4-O-benzyl group. The pyranoid product tetra-O-benzyl-1,5-anhydro-D-glucitol preponderates when the intermediate 2,3,4,6-tetra-O-toluene-p-sulphonyl-D-glucitol (6) is converted into its 0-5 oxyanion. Benzyloxy participation has been exploited in a new synthesis of 2,3,5-tri-O-benzyl-a (and ß)-D-ribofuranosylethyne, (20) and (4), from 2,3,4,5-tetra-O-benzyl-aldehydo-D-ribose. A synthesis of 2-a-D-ribofuranosylmaleimide, the a-isomer of showdomycin, from (20) is described.

T1 - C-nucleoside studies. Part 13. A new synthesis of 2,3,5-tri-O-benzyl- α(and β)-D-ribofuranosylethyne involving benzyloxy participation, and a synthesis of α-showdomycin

Two total syntheses of showdomycin and related …

Showdomycin analogs: synthesis and antitumor …

STE REOCONTROLLED SYNTHESIS OF SHOWDOMYCIN AND 6-AZAPSEUDOURIDINES1 T

Two novel analogues, 2 and 3, of the C-riboside showdomycin (1) have been prepared by exploiting the N-TIPS-substituted pyrrole 7 as a synthetic equivalent for the maleimide C3 anion. The tetraacetate precursor, 12, of target 2 as well as target 3 itself

The effect of showdomycin on the syntheses of deoxyribonucleotides from various pyrimidine and purine derivatives was studied in cell-free systems from
The formations of deoxycytidine phosphates, deoxyuridine phosphates, deoxyguanosine phosphates and deoxyadenosine phosphates from the corresponding ribonucleoside diphos-phates were all inhibited by low concentrations of showdomycin. The formation of deoxythymidine phosphates from dUMP was also very susceptible to the antibiotic. These inhibitory actions of showdomycin could be reversed by a sulfhydryl compound (mercaptoethanol) but not by nucleosides, in contrast to a previous finding that the in-hibitory action of this antibiotic on the cell growth was reversed by compounds belonging to both of these groups.
N-Ethylmaleimide (NEM), a thiol reagent which has a structure related to the aglycone moiety of showdomycin, was also found to be a potent inhibitor of both the reduction of CDP and the methylation of dUMP as showdomycin. A mercurial thiol reagent, -chloro-mercuribenzoic acid (PCMB), however, was found to be inactive against the methylation of dUMP although the salvage synthesis of dUMP was inhibited by low concentrations of this reagent.
The formations of deoxythymidine phosphates and of deoxyuridine phosphates from their respective pyrimidine bases and a deoxyribosyl donor were quite resistant to showdomycin.

A synthesis of β-2′-deoxyshowdomycin - ResearchGate

AB - 2,3,4,6-Tetra-O-benzyl-D-glucitol (5) reacts with toluene-p-sulphonyl chloride in pyridine at 60°C to form mainly the furanoid products 2,3,6-tri-O-benzyl-1,4-anhydro-D-glucitol (10) and its 5-toluene-p-sulphonate (11) with loss of the 4-O-benzyl group. The pyranoid product tetra-O-benzyl-1,5-anhydro-D-glucitol preponderates when the intermediate 2,3,4,6-tetra-O-toluene-p-sulphonyl-D-glucitol (6) is converted into its 0-5 oxyanion. Benzyloxy participation has been exploited in a new synthesis of 2,3,5-tri-O-benzyl-a (and ß)-D-ribofuranosylethyne, (20) and (4), from 2,3,4,5-tetra-O-benzyl-aldehydo-D-ribose. A synthesis of 2-a-D-ribofuranosylmaleimide, the a-isomer of showdomycin, from (20) is described.

The synthesis of showdomycin and its analogues - ROS …

N2 - 2,3,4,6-Tetra-O-benzyl-D-glucitol (5) reacts with toluene-p-sulphonyl chloride in pyridine at 60°C to form mainly the furanoid products 2,3,6-tri-O-benzyl-1,4-anhydro-D-glucitol (10) and its 5-toluene-p-sulphonate (11) with loss of the 4-O-benzyl group. The pyranoid product tetra-O-benzyl-1,5-anhydro-D-glucitol preponderates when the intermediate 2,3,4,6-tetra-O-toluene-p-sulphonyl-D-glucitol (6) is converted into its 0-5 oxyanion. Benzyloxy participation has been exploited in a new synthesis of 2,3,5-tri-O-benzyl-a (and ß)-D-ribofuranosylethyne, (20) and (4), from 2,3,4,5-tetra-O-benzyl-aldehydo-D-ribose. A synthesis of 2-a-D-ribofuranosylmaleimide, the a-isomer of showdomycin, from (20) is described.

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A SYNTHESIS OF $-2'-DEOXYSHOWDOMYCIN ..


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