GB966837A - Halogen-substituted pyranose derivatives and the manufacture and conversion thereof - Google Patents

Halogen-substituted pyranose derivatives and the manufacture and conversion thereof

Info

Publication number
GB966837A
GB966837A GB1895063A GB1895063A GB966837A GB 966837 A GB966837 A GB 966837A GB 1895063 A GB1895063 A GB 1895063A GB 1895063 A GB1895063 A GB 1895063A GB 966837 A GB966837 A GB 966837A
Authority
GB
United Kingdom
Prior art keywords
fluoride
bromide
chloride
benzoyl
conversion
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB1895063A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB966837A publication Critical patent/GB966837A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/12—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by acids having the group -X-C(=X)-X-, or halides thereof, in which each X means nitrogen, oxygen, sulfur, selenium or tellurium, e.g. carbonic acid, carbamic acid
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Saccharide Compounds (AREA)

Abstract

Novel compounds of the general formula: <FORM:0966837/C1/1> where R is nitrophenyl or cyanomethyl group and X is a halogen atom, the two alkyl groups in the 5-position are identical and the asterisks denote that the conformation of the bonds on carbon atoms are appropriate to an alpha glycoside, are made by halogenating, with concommittat ether fission a glycoside of the general formula: <FORM:0966837/C1/2> where the terms are as defined above. Preferred are the 2-O-benzoyl or para methoxy benzoyl derivatives. Per se claimed are 5, 5-dimethyl -4- (O methyl) -3- (O p-nitro-phenyloxy carbonyl) -2- (O benzoyl) -L- alpha lyxopyranosyl bromide, chloride and fluoride. The bromides are prepared by the use of hydrogen bromide in glacial acetic acid, the chlorides by hydrogen chloride in nitromethane or with dichloromethyl methyl ether in the presence of a catalytic amount of a Lewis acid; the chloride and the fluoride may be obtained from the bromide by treatment in an inert solvent with silver chloride or fluoride respectively. A further process for the preparation of the fluoride consists of the successive treatment of the bromide with silver carbonate followed by hydrogen fluoride. The product may be converted into an aryl glycoside by reaction, in acidic medium with a phenol or a substituted phenol, and if desired the 3-(O substituent) may be replaced by the carbamoyl group e.g. with alcoholic ammonia and the O-acyl group in position 2 can be hydrolysed e.g. by alcoholic barium alkoxide solution. In the examples are described the preparation of 5, 5-dimethyl -4- (O methyl) -3- [O(p-nitrophenyloxy carbonyl)] -2- (O benzoyl)- -L- alpha lyxopyranosyl bromide, its conversion to the chloride and fluoride; treatment thereof with silver carbonate to yield the pyranose and the conversion of the pyranose to the fluoride is also featured. The direct synthesis of the chloride and the reaction of the bromide with orthocresol to yield the pyranoside are also described.
GB1895063A 1961-01-27 1962-01-26 Halogen-substituted pyranose derivatives and the manufacture and conversion thereof Expired GB966837A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH98461A CH419082A (en) 1961-01-27 1961-01-27 Process for the production of sugar derivatives

Publications (1)

Publication Number Publication Date
GB966837A true GB966837A (en) 1964-08-19

Family

ID=4199761

Family Applications (2)

Application Number Title Priority Date Filing Date
GB1895063A Expired GB966837A (en) 1961-01-27 1962-01-26 Halogen-substituted pyranose derivatives and the manufacture and conversion thereof
GB305562A Expired GB950251A (en) 1961-01-27 1962-01-26 Novel sugar derivatives and their manufacture

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB305562A Expired GB950251A (en) 1961-01-27 1962-01-26 Novel sugar derivatives and their manufacture

Country Status (3)

Country Link
BE (1) BE612831A (en)
CH (1) CH419082A (en)
GB (2) GB966837A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4617386A (en) * 1983-04-25 1986-10-14 The United States Of America As Represented By The United States Department Of Energy Process for the production of 18 F-2-deoxy-2-fluoro-D-glucose

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4617386A (en) * 1983-04-25 1986-10-14 The United States Of America As Represented By The United States Department Of Energy Process for the production of 18 F-2-deoxy-2-fluoro-D-glucose

Also Published As

Publication number Publication date
BE612831A (en) 1962-07-19
CH419082A (en) 1966-08-31
GB950251A (en) 1964-02-26

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