FR2400032A1 - 5-Hydroxy-macro:lactone derivs. and glucopyranosyl ether(s) - intermediates for macrolide antibiotics - Google Patents

5-Hydroxy-macro:lactone derivs. and glucopyranosyl ether(s) - intermediates for macrolide antibiotics

Info

Publication number
FR2400032A1
FR2400032A1 FR7834348A FR7834348A FR2400032A1 FR 2400032 A1 FR2400032 A1 FR 2400032A1 FR 7834348 A FR7834348 A FR 7834348A FR 7834348 A FR7834348 A FR 7834348A FR 2400032 A1 FR2400032 A1 FR 2400032A1
Authority
FR
France
Prior art keywords
intermediates
macrolide antibiotics
derivs
glucopyranosyl
lactone
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.)
Granted
Application number
FR7834348A
Other languages
French (fr)
Other versions
FR2400032B1 (en
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.)
Microbial Chemistry Research Foundation
Original Assignee
Microbial Chemistry Research Foundation
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
Priority claimed from JP2561977A external-priority patent/JPS53111089A/en
Priority claimed from JP2561877A external-priority patent/JPS53111088A/en
Application filed by Microbial Chemistry Research Foundation filed Critical Microbial Chemistry Research Foundation
Publication of FR2400032A1 publication Critical patent/FR2400032A1/en
Application granted granted Critical
Publication of FR2400032B1 publication Critical patent/FR2400032B1/fr
Granted legal-status Critical Current

Links

Classifications

    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins

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

Macrolides of formula (I) are new (Bond a is single or double. Bond b is single or double, or is an oxiran-2,3-yl.gp. The dotted lines complete a 16- or 17-membered ring. 2 is either H (Cpds. (Ia)) or the gp. (II). (Cpds. (Ib)). A is carbonyl or RO . R is H, acyl or forosaminyl. R1 is aldehyde gp. protected as cyclic acetal or thioacetal. R2=H or acyl. R3= lower alkyl. R4=H, CH2OH or mycinosyloxymethyl. R5=CH3 or CH3O. R6=H or CH3). (I) are intermediates for new macrolide antibiotics. New sugar residues or other substits. can be introduced easily without formation of an intramolecular cyclic acetal. In an example 6-(1,3-dioxolan-2-yl)methyl-3,5-dihydroxy-14-hydroxymethyl-4,8,12- -trimethyl-9-oxo-10,12-heptadecadien-15-olide was prepd. from the corresp. 5-(3,6-dideoxy-3-Me2N-beta-D-glucopyranosloxy) by reaction with m-Cl-perbenzoic acid and Ac2O.
FR7834348A 1977-03-09 1978-12-06 5-Hydroxy-macro:lactone derivs. and glucopyranosyl ether(s) - intermediates for macrolide antibiotics Granted FR2400032A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2561977A JPS53111089A (en) 1977-03-09 1977-03-09 Novel macrolide compound and its preparation
JP2561877A JPS53111088A (en) 1977-03-09 1977-03-09 Novel macrolactone derivative and its preparation

Publications (2)

Publication Number Publication Date
FR2400032A1 true FR2400032A1 (en) 1979-03-09
FR2400032B1 FR2400032B1 (en) 1982-06-11

Family

ID=26363262

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7834348A Granted FR2400032A1 (en) 1977-03-09 1978-12-06 5-Hydroxy-macro:lactone derivs. and glucopyranosyl ether(s) - intermediates for macrolide antibiotics

Country Status (2)

Country Link
DE (1) DE2858223C2 (en)
FR (1) FR2400032A1 (en)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2243948A1 (en) * 1973-09-19 1975-04-11 Toyo Jozo Kk

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2243948A1 (en) * 1973-09-19 1975-04-11 Toyo Jozo Kk

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
EXBK/ *
EXBK/77 *

Also Published As

Publication number Publication date
FR2400032B1 (en) 1982-06-11
DE2858223C2 (en) 1989-04-06

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