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GB1171128A - Process for the Preparation of 4alpha-Hydroxy-5beta-Steroids - Google Patents

Process for the Preparation of 4alpha-Hydroxy-5beta-Steroids

Info

Publication number
GB1171128A
GB1171128A GB4953366A GB4953366A GB1171128A GB 1171128 A GB1171128 A GB 1171128A GB 4953366 A GB4953366 A GB 4953366A GB 4953366 A GB4953366 A GB 4953366A GB 1171128 A GB1171128 A GB 1171128A
Authority
GB
United Kingdom
Prior art keywords
keto
steroids
hydroxy
preparation
bisnor
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
GB4953366A
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.)
Zoecon Corp
Original Assignee
Zoecon Corp
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 US506410A external-priority patent/US3378549A/en
Priority claimed from US523032A external-priority patent/US3354152A/en
Priority claimed from US523019A external-priority patent/US3354154A/en
Application filed by Zoecon Corp filed Critical Zoecon Corp
Publication of GB1171128A publication Critical patent/GB1171128A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J71/00Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N45/00Biocides, pest repellants or attractants, or plant growth regulators, containing compounds having three or more carbocyclic rings condensed among themselves, at least one ring not being a six-membered ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J75/00Processes for the preparation of steroids in general
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J9/00Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Steroid Compounds (AREA)

Abstract

1,171,128. Preparation of 6-keto-#<SP>7</SP>-14α- hydroxy-5#-steroids. ZOECON CORP. 4 Nov., 1966 [4 Nov., 1965; 26 Jan., 1966 (2); 26 May, 1966], No. 49533/66. Heading C2U. 6 - Keto - #<SP>7</SP> - 14α - hydroxy - 5# - steroids are prepared by treating 6-keto-#<SP>7</SP>-5α-steroids unsubstituted in position 14 and having a hydrogen atom or an acyloxy group in the 5α- position with selenium dioxide, when the 5α- steroid has a 5α-acyloxy group, selectively replacing this with a 5α-hydrogen atom by treatment with chromous chloride, and inverting the configuration of the 5α-H to 5#-H by treatment with a base. Preferred starting materials are 2#,3#,5α - triacetoxy - 6 - keto - 22,23 - bisnor - 5α - chol - 7 - enoic acid methyl ester (giving as final product 2#,3#,14α - trihydroxy - 6 - keto - 22,23 - bisnor- 5# - chol - 7 - enoic acid methyl ester) and a 2#,3#,22#,25 - tetrahydroxy - 5α - cholest- 7-en-6-one in which OH groups are optionally protected by ester, ketal or ether formation (giving as final product 2#,3#,14α,22#,25-pentahydroxycholest-7-en-6-one).
GB4953366A 1965-11-04 1966-11-04 Process for the Preparation of 4alpha-Hydroxy-5beta-Steroids Expired GB1171128A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US506410A US3378549A (en) 1965-11-04 1965-11-04 2, 3-acetonides of polyhydroxy bis norchol-7-enoic acid derivatives
US523032A US3354152A (en) 1966-01-26 1966-01-26 2beta, 3beta-alkylidenedioxy-6-oxygenated-delta-steroids and process for the preparation thereof
US523019A US3354154A (en) 1966-01-26 1966-01-26 2beta, 3beta-alkylidenedioxy-6-hydroxy-22, 23-bisnorchol-7-enoic acid alkyl esters and process for the production thereof
US55304166A 1966-05-26 1966-05-26

Publications (1)

Publication Number Publication Date
GB1171128A true GB1171128A (en) 1969-11-19

Family

ID=27504457

Family Applications (3)

Application Number Title Priority Date Filing Date
GB4953366A Expired GB1171128A (en) 1965-11-04 1966-11-04 Process for the Preparation of 4alpha-Hydroxy-5beta-Steroids
GB4953466A Expired GB1171129A (en) 1965-11-04 1966-11-04 Improvements in or relating to Ecdysone Steroids
GB4953266A Expired GB1174082A (en) 1965-11-04 1966-11-04 Improvements concerned with Steroids related to Ecdysone

Family Applications After (2)

Application Number Title Priority Date Filing Date
GB4953466A Expired GB1171129A (en) 1965-11-04 1966-11-04 Improvements in or relating to Ecdysone Steroids
GB4953266A Expired GB1174082A (en) 1965-11-04 1966-11-04 Improvements concerned with Steroids related to Ecdysone

Country Status (3)

Country Link
DE (3) DE1593453A1 (en)
FR (1) FR1502168A (en)
GB (3) GB1171128A (en)

Also Published As

Publication number Publication date
FR1502168A (en) 1967-11-18
GB1174082A (en) 1969-12-10
DE1593453A1 (en) 1970-07-16
DE1593454A1 (en) 1971-01-28
GB1171129A (en) 1969-11-19
DE1593452A1 (en) 1970-07-16

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