JPS5598199A - Preparation of 25-hydroxy cholesta-1,4,6-trien-3-one - Google Patents

Preparation of 25-hydroxy cholesta-1,4,6-trien-3-one

Info

Publication number
JPS5598199A
JPS5598199A JP291979A JP291979A JPS5598199A JP S5598199 A JPS5598199 A JP S5598199A JP 291979 A JP291979 A JP 291979A JP 291979 A JP291979 A JP 291979A JP S5598199 A JPS5598199 A JP S5598199A
Authority
JP
Japan
Prior art keywords
formula
compound
oxidized
cholesta
trien
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
JP291979A
Other languages
Japanese (ja)
Other versions
JPS6144879B2 (en
Inventor
Akisuke Saiga
Kunishige Sugiyama
Seiichiro Nomoto
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.)
Eisai Co Ltd
Original Assignee
Eisai Co Ltd
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 Eisai Co Ltd filed Critical Eisai Co Ltd
Priority to JP291979A priority Critical patent/JPS5598199A/en
Publication of JPS5598199A publication Critical patent/JPS5598199A/en
Publication of JPS6144879B2 publication Critical patent/JPS6144879B2/ja
Granted legal-status Critical Current

Links

Classifications

    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Steroid Compounds (AREA)

Abstract

PURPOSE: To obtain the title compound which is an intermediate for active vitamin D3 analogs, by using inexpensive lithocholic acid easily available in a large quantity as a starting material.
CONSTITUTION: Easily available lithocholic acid of formula I is esterified with a lower alkanol, and oxidized with Jone's reagent to give a compound of formula II, which is reacted with 2-methyl-2-ethyl-1,3-dioxolan, and hydrogenated with LiAlH4, then oxidized with pyridinium chlorochromate to form a compound of formula III. The resulting compound is reacted with triphenylphosphine isopropylidene reagent, oxidized with an organic peracid, and hydrogenated with lithium aluminum hydride to afford a compound of formula IV, whose protecting group is eliminated with an inorganic acid. A double bond is then introduced to form 25-hydroxy cholesta-1,4,6-trien-3-one of formula V in an overall yield ≥ 5.5%. 1,25-Dihydroxy cholecaciferol can be obtained from the compound of formula V.
COPYRIGHT: (C)1980,JPO&Japio
JP291979A 1979-01-17 1979-01-17 Preparation of 25-hydroxy cholesta-1,4,6-trien-3-one Granted JPS5598199A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP291979A JPS5598199A (en) 1979-01-17 1979-01-17 Preparation of 25-hydroxy cholesta-1,4,6-trien-3-one

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP291979A JPS5598199A (en) 1979-01-17 1979-01-17 Preparation of 25-hydroxy cholesta-1,4,6-trien-3-one

Publications (2)

Publication Number Publication Date
JPS5598199A true JPS5598199A (en) 1980-07-25
JPS6144879B2 JPS6144879B2 (en) 1986-10-04

Family

ID=11542753

Family Applications (1)

Application Number Title Priority Date Filing Date
JP291979A Granted JPS5598199A (en) 1979-01-17 1979-01-17 Preparation of 25-hydroxy cholesta-1,4,6-trien-3-one

Country Status (1)

Country Link
JP (1) JPS5598199A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01117895A (en) * 1987-10-29 1989-05-10 Teijin Ltd Production of cholesta-1,4,6-trien-3-ones
JPH0578388A (en) * 1982-05-26 1993-03-30 Wisconsin Alumni Res Found 25,26,27-trinor-1alpha,2beta-epoxycholesta-4,6-dien-3-one-24acid methyl ester

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0578388A (en) * 1982-05-26 1993-03-30 Wisconsin Alumni Res Found 25,26,27-trinor-1alpha,2beta-epoxycholesta-4,6-dien-3-one-24acid methyl ester
JPH01117895A (en) * 1987-10-29 1989-05-10 Teijin Ltd Production of cholesta-1,4,6-trien-3-ones

Also Published As

Publication number Publication date
JPS6144879B2 (en) 1986-10-04

Similar Documents

Publication Publication Date Title
JPS5731694A (en) Preparation of sucrose ester with fatty acid
JPS5598199A (en) Preparation of 25-hydroxy cholesta-1,4,6-trien-3-one
JPS52806A (en) Preparation of ester
JPS5598200A (en) Preparation of 24xi, 25-dihydroxycholesta-1,4,6-trien-3-one
JPS5424821A (en) Preparation of fluoric acid fluoride containing ester group
JPS53127409A (en) Preparation of unsaturated ester
JPS53124250A (en) Preparation of vitamin d3
JPS5424818A (en) Preparation of high purity maleic acid monoalcohol ester
JPS5573700A (en) Preparation of steroidal ketone compound
JPS5269880A (en) Producing emulsified liquid of hindered esters
JPS5420195A (en) Preparation of guanosine-5'-monophosphoric acid
JPS55153799A (en) Preparation of 3alpha-hydroxy-keto-cholanic acid
JPS5527161A (en) Production of alcohol or its ether derivative
JPS5738799A (en) 25-hydroxy-3,24-dioxocholesta-1,4,6-trienes and their preparations
JPS55124736A (en) Preparation of dihydro-coenzyme q diacetate
JPS554345A (en) Optically active steroid intermediate and its preparation
JPS5742643A (en) 6,10,14,18-tetramethyl-5,9,13,17-nonadecatetraene-2-ol
JPS5373529A (en) Preparation of hydroquinone
JPS55160739A (en) Preparation of cyclopentenone compound
JPS55160740A (en) Preparation of cyclopentenolone
JPS5522625A (en) Preparation of epoxyditerpene
JPS5564538A (en) Preparation of dihydrocoenzyme q compound
JPS53130619A (en) Preparation of high purity isoprenylacetic acid
JPS5436249A (en) 24-oxocholest-5-en-3beta2-ol dand preparation of its esters
JPS6429396A (en) Castasterone derivative