Cupps et al., 1982 - Google Patents

Use of allyltrimethylsilane in the formation of potential C-nucleoside precursors

Cupps et al., 1982

Document ID
2484854137685273068
Author
Cupps T
Wise D
Townsend L
Publication year
Publication venue
The Journal of Organic Chemistry

External Links

Snippet

The soft nucleophile allyltrimethylsilane reacted with l-0-acetyl-2, 3, 5-tri-0-benzoyl-/3-D- ribofuranose under Lewis acid catalysis to afford the novel allyl sugar 4, 7-anhydro-l, 2, 3- trideoxy-5, 6, 8-tri-0-benzoyl-D-aZtro-(oZZo)-oct-l-ene (1) as an anomeric mixture …
Continue reading at pubs.acs.org (other versions)

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/16—Purine radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by C07D451/00 - C07D477/00
    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
    • C07D487/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00

Similar Documents

Publication Publication Date Title
Cupps et al. Use of allyltrimethylsilane in the formation of potential C-nucleoside precursors
Zhang et al. Syntheses of 2'-deoxypseudouridine, 2'-deoxyformycin B, and 2', 3'-dideoxyformycin B by palladium-mediated glycal-aglycon coupling
Otter et al. Nucleosides. LVIII. Transformations of pyrimidine nucleosides in alkaline media. 3. Conversion of 5-halouridines into imidazoline and barbituric acid nucleosides
Horton The Anomeric 1, 3, 4, 6-Tetra-O-acetyl-2-deoxy-2-(2, 4-dinitroanilino)-D-glucopyranoses
CA1060003A (en) N-trifluoroacetyladriamycin-14-alkanoates and therapeutic compositions containing same
US4595678A (en) N-substituted pseudo-aminosugars and pharmaceutical compositions containing same
US4537882A (en) 4-Demethoxy-3'-desamino-2'-halo-anthracycline and pharmaceutical composition containing same
Holý Synthesis of 1-[3-deoxy-β-D-psicofuranosyl] uracil and related compounds
Spohr et al. Molecular recognition XI. The synthesis of extensively deoxygenated derivatives of the H-type 2 human blood group determinant and their binding by an anti-H-type 2 monoclonal antibody and the lectin 1 of Ulex europaeus
US6043367A (en) Proactive antitumor compounds
CN102146107B (en) Synthesis and anti-tumor activity of (S)-2-hydroxyalkyl-1,4-dihydroxyl-9-10-anthraquinone and glycosyl conjugates
Gupta et al. C-glycosyl nucleosides. 9. An approach to the synthesis of purine-related C-glycosides
US4691012A (en) Sialic acid derivative and process for preparing the same
JPS63258485A (en) Antitumor anthracycline glycoside, its production and intermediate product, composition and use thereof
DE3719377C2 (en) Anthracycline glycosides, processes for their preparation and medicaments containing them
Koole et al. Synthesis and Conformation of 9-(3'-&Methyl-ß-oxy/o4uranosyl)-adenine and 3-C-Methyladenosine, Two Sugar-Methylated Nucleoside Analogues
YAMASHITA et al. Studies on Antitumor Agents. VII. Antitumor Activities of O-Alkoxyalkyl Derivatives of 2'-Deoxy-5-trifluoromethyluridine
Cupps et al. A novel three-step synthesis of a pyrrolo [3, 2-d] pyrimidine C-nucleoside
Revankar et al. A convenient synthesis of certain 1‐(β‐D‐ribofuranosyl) benzotriazoles
JPS63141992A (en) Novel anthracycline derivative and production thereof
Glaudemans et al. Synthesis of the Two 2-O-Nitro-3, 5-di-Op-nitrobenzoyl-D-arabinofuranosyl Chlorides, an Anomeric Pair of Crystalline Pentofuranosyl Halides Having a Nonparticipating Group at C-2
Lee et al. Preparation of guanine pentofuranosyl nucleosides using a Friedel-Crafts catalyst
Joos et al. Synthesis and biological evaluation of 4-carbamoyl-2-β-D-ribofuranosyl-pyridine
Wolfrom et al. A novel reaction of a nitro sugar with alcohols
Groziak et al. Definitive Solution Structures for the 6-Formylated Versions of 1-(βD-Ribofuranosyl)-, 1-(2′-Deoxy-β-D-Ribofuranosyl)-, and 1-β-D-Arabinofuranosyluracil, and of Thymidine