DE1768470A1 - 1,2-O-Isopropylidine-5-O-benzoyl-3-methyl-alpha-D-ribofuranose and process for its preparation - Google Patents

1,2-O-Isopropylidine-5-O-benzoyl-3-methyl-alpha-D-ribofuranose and process for its preparation

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Publication number
DE1768470A1
DE1768470A1 DE19661768470 DE1768470A DE1768470A1 DE 1768470 A1 DE1768470 A1 DE 1768470A1 DE 19661768470 DE19661768470 DE 19661768470 DE 1768470 A DE1768470 A DE 1768470A DE 1768470 A1 DE1768470 A1 DE 1768470A1
Authority
DE
Germany
Prior art keywords
benzoyl
methyl
preparation
ribofuranose
isopropylidine
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.)
Pending
Application number
DE19661768470
Other languages
German (de)
Inventor
Edward Walton
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.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
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 Merck and Co Inc filed Critical Merck and Co Inc
Publication of DE1768470A1 publication Critical patent/DE1768470A1/en
Pending legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H9/00—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical
    • C07H9/02—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical the hetero ring containing only oxygen as ring hetero atoms
    • C07H9/04—Cyclic acetals
    • 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
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
    • 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
    • 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
    • C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
    • C07H7/02—Acyclic radicals

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)

Description

DR.-ING. WALTER ABITZ DR. DIETER F. MORF DR. HANS-A. BRAUNSDR.-ING. WALTER ABITZ DR. DIETER F. MORF DR. HANS-A. BROWN

PatentanwältePatent attorneys

München,Munich,

Postanschrift/ Postal Address 8 München 86, Postfach 860109Postal address 8 München 86, PO Box 860109

Pienzenauerstraße 28 Telefon 483225 und 486415 Telegramme: Chemindus MünchenPienzenauerstraße 28 Tel. 483225 and 486415 Telegrams: Chemindus Munich

23. April 1970 12 118April 23, 1970 12 118

P 17 68 470. 7-42 Neu· UnterlagenP 17 68 470. 7-42 New · documents

MEHCK & CO., INCORPORATED 126 Säst Lincoln Avenue, Rahway, New Jersey 07065, V.St.A.MEHCK & CO., INCORPORATED 126 Sat Lincoln Avenue, Rahway, New Jersey 07065, V.St.A.

2-0-Xsopropylidin-5-0-benzoyl-;VaethylHi-D-rLboftiranoee und Verfahren zu Ihrer Herstellung2-0-Xsopropylidin-5-0-benzoyl-; VaethylHi-D-rLboftiranoee and method of making them

Die Erfindung betrifft l,2-0-Ieopropylidin-5-0-benzoyl-;5-methyl-a-D-ribofuranose und ein Verfahren su ihrer Herstellung« The invention relates to 1,2-0-Ieopropylidin-5-0-benzoyl-; 5-methyl-a-D-ribofuranose and a process for their manufacture «

Die neue erfindungsgemäss erhältlich· Verbindung kann durch die folgende Strukturformel wiedergegeben werden:The new compound obtainable according to the invention can be obtained by the following structural formula can be reproduced:

ßAD ß AD

109920/202·109920/202

18 11818 118

erflndungegealae erhiltllohe Verbindung wird hergestellt»inventively obtainable connection is established »

ait einea NethrlaagneAluabalogenld unter Bildung von 3-O-Bensorl-l,8- 0- ieopropgrUdin-^-eethyl- ο- D-rlboiuranoee behandelt wird.ait a NethrlaagneAluabalogenld with the formation of 3-O-Bensorl-l, 8- 0- ieopropgrUdin- ^ - eethyl- ο- D-rlboiuranoee treated will.

Dl· Arbeiteiielaen sur Beretellung der erflndungegeales erhMltllohMi Verbindung aelgt da« folgend« HeaktionMenoaatDl · Arbeitseiielaen on the provision of the unequaled income Connection is there «following« HeaktionMenoaat

IIII

(Orignard-Reagene) (Orignard reagents)

Hierbei bedeutet X Belogen.Here, X means lied.

Oeneuer «uJigedrOolct wird dl· erfindungig—Mm erhältliohe Verbindung erhalten, lad·« SiOThe present invention becomes the present invention - Mm obtainable Get in touch, lad · «SiO

U*enrthro->pentulofuranoe· alt eine« Orlgnard-Reagene in la weventlietieii atojmioMtrleehen Mengen in eines Teapfraturbereieh von k%m Ä 9O bl· etwa 80 0Q etna aiii paar Minuten bia ot«a 5 »tundan u|it«r Bildung ·ΐη*τ 5-0 Beniojl-l^-O^leopro«U * enrthro-> pentulofuranoe · old a «Orlgnard reagent in la weventlietieii atojmioMtrleehen quantities in a tea temperature range of k% m Ä 9 O bl · about 80 0 Q etna aiii few minutes bia ot« a 5 »tundan u | it« r Education · ΐη * τ 5-0 Beniojl-l ^ -O ^ leopro «

l^p· uagtsetit wird. 01· bei die •er Realrtio» fafiiiaditen OrlgaTd*magontlen aind Nethylaag-l ^ p uagtsetit will. 01 · at the • he Realrtio »fafiiiaditen OrlgaTd * magontlen aind Nethylaag-

U grignard ^tien alnd MelaitUfiaaanaal iiitii inΊιΊ tw^i Metlnrlaacne-U grignard ^ tien alnd MelaitUfiaaanaal iiitii inΊιΊ tw ^ i Metlnrlaacne-

BAD ORIGINALBATH ORIGINAL

12 Il8 912 Il8 9

BlHPHl 1BlHPHl 1

Ein Orlgnard-Reaeene, Methylaagheslunjodld, hergestellt aus 690 ag (26,4 BMoI) Magnesiua und 3*85 g (27,5 HMoI) MethylJodid in 32 al trockene· Xther, wird su einer gerührten Lösung von 1,0 g (3,43 "MoI) !,a-O-Iiopropylidin-S-O-benioyl-a-D-•rytnro-2-pentulofurenoee in 100 al trockenen Xther alt 5 0O gegeben. Maeh etwa 3 Stunden wird die Reaktlönsaieohung in eine Mlsohung von 50 g Aaaonluaohlorld, 200 al Bis und Wasser, und 200 al Xther gegossen · Die Sohl oh ten werden getrennt und die wässrige Phase wird sweiaal ait Je 150 al Xther extrahiert. Die getrocknete XtherlSsung (MgSO^) wird sur Trockne konsentrlert und der Rttokstand (1,24 g) wird aus Xther kristallisiert. Es werden insgesaat 524 ag 1,2-0-Isopropjlidln~5-0~ benzoyl-3-aethyl-a-D-ribofuranose erhalten, Fp. * 109 bis 111 0C.An Orlgnard Reaeene, Methylaagheslunjodld, prepared from 690 ag (26.4 BMoI) magnesia and 3 * 85 g (27.5 HMoI) methyl iodide in 32 al dry Xther, is added to a stirred solution of 1.0 g (3, 43 "MoI)!, AO-Iiopropylidin-SO-benioyl-aD- • rytnro-2-pentulofurenoee given in 100 al dry Xther old 5 0 O. For about 3 hours the reaction solution is in a solution of 50 g Aaaonluaohlorld, 200 al The soles are separated and the aqueous phase is extracted every 150 ml. The dried ether solution (MgSO ^) is concentrated to dryness and the reagent level (1.24 g) is removed crystallized from Xther. There are insgesaat 524 ag 1,2-0-Isopropjlidln ~ 5-0 ~ benzoyl-3-ethyl-D-ribofuranose, mp. 109 to 111 * 0 C.

Beispiel 2Example 2

Ein Orlgnard-Reagens, Methylaagnesluabroaid, hergestellt aus 690 ag (28,4 aMol) Jfagneslua und 2,61 g (27,5 «Hol) Methylbre-Bid in 32 al trocken·· Xther, wird su einer gerührten Lesung von 1,0 g (3,42 «Mol) 1,2-0-1 eopropyUdin-5-Q-bettfoyl-a-D-erythro-3-pentulofüranose in 100 al trookenea Xther alt 5 0C gegeben. Haoh etwa 3 Stunden wird die RealrtlonaalBOhfciiig in ·!&·- Mlsohung von 50 g Aaaoniuaehlorld, 200 al Bis und Vasier, und 200 al Xther gegossen. Die Sohlohten werden getrennt und dl« wässrige Schicht wird sweiaal alt Je 150 al Xther extrahiert. Die getrocknete Xtherlttsung (MgSO4) wird sur froekn* konsentrlert und der Rttokstand (1,24 g) wird aus Xther kristaJLll* eiert. Bs werden lnsaeaaait 524 ag l,2«0-Iiopropylidisi-5-0-befi- *oyl-3HBethyl-a-D-rlbofi*2»«i5©»e erhalten, Fp. 109 Mi 111 0O.An Orlgnard reagent, Methylaagnesluabroaid, prepared from 690 ag (28.4 aMol) of Jfagneslua and 2.61 g (27.5% Hol) Methylbre-Bid in 32 al dry Xther, is given a stirred reading of 1.0 g (3.42 moles) 1,2-0-1 eopropyUdin-5-Q-bed foyl-aD-erythro-3-pentulofuranose in 100 al trookenea Xther old 5 0 C given. After about 3 hours, the RealrtlonaalBOhfciiig is poured into ·! & · - Mlsung of 50 g Aaaoniuaehlorld, 200 al Bis and Vasier, and 200 al Xther. The soles are separated and the aqueous layer is extracted every 150 times. The dried thermal solution (MgSO 4 ) is concentrated on the surface and the residue (1.24 g) is crystallized from ether. Insaeaait 524 ag 1.2 "0-Iiopropylidisi-5-0-befi- * oyl-3HBethyl-aD-rlbofi * 2""i5" e obtained, m.p. 109 Mi 111 0 O.

' * : 10Sa2G/203i'*: 10Sa2G / 203i

Claims (2)

23· April 1970 12 118 P ate nt an a p r Uo he23 April 1970 12 118 P ate nt an a p r Uo he 1. 1,2-0-l80propylidin=5-0-benzoyl-^-methyl-a-D-ribofuranoee,1. 1,2-0-180propylidine = 5-0-benzoyl - ^ - methyl-a-D-ribofuranoee, 2. Verfahren asur Herstellung der Verbindung gemüse Anepruoh 1« daduroh gekennzeichnet, dass man 5-0-Benzoyl-l,2-0-isopropylidin^-D-erythro-3-pentulofuranose der Formel2. Process asur the preparation of the compound vegetables Anepruoh 1 «daduroh characterized in that one 5-0-benzoyl-1,2-0-isopropylidin ^ -D-erythro-3-pentulofuranose the formula C6H5COOCHC 6 H 5 COOCH mit einem Methylmagneeiumhalogenid umsetzt, das erhaltene Umsetzungsprodukt hydrolysiert und daraus das gewünschte Produkt isoliert.with a Methylmagneeiumhalogenid reacted, the obtained Reaction product hydrolyzed and the desired product isolated therefrom. 109820/2038109820/2038 Neue Unterlagsn " : '■' New documents " : '■' ur.gB<je«.v.ur.gB <je «.v.
DE19661768470 1965-11-15 1966-11-14 1,2-O-Isopropylidine-5-O-benzoyl-3-methyl-alpha-D-ribofuranose and process for its preparation Pending DE1768470A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US50769765A 1965-11-15 1965-11-15

Publications (1)

Publication Number Publication Date
DE1768470A1 true DE1768470A1 (en) 1971-05-13

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ID=24019753

Family Applications (2)

Application Number Title Priority Date Filing Date
DE19661768470 Pending DE1768470A1 (en) 1965-11-15 1966-11-14 1,2-O-Isopropylidine-5-O-benzoyl-3-methyl-alpha-D-ribofuranose and process for its preparation
DE19661593110 Pending DE1593110A1 (en) 1965-11-15 1966-11-14 Ribofuranoses and processes for their preparation

Family Applications After (1)

Application Number Title Priority Date Filing Date
DE19661593110 Pending DE1593110A1 (en) 1965-11-15 1966-11-14 Ribofuranoses and processes for their preparation

Country Status (5)

Country Link
CH (1) CH490367A (en)
DE (2) DE1768470A1 (en)
FR (1) FR1498856A (en)
GB (1) GB1163102A (en)
NL (1) NL6616102A (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MY164523A (en) 2000-05-23 2017-12-29 Univ Degli Studi Cagliari Methods and compositions for treating hepatitis c virus
KR20030036189A (en) 2000-05-26 2003-05-09 이데닉스(케이만)리미티드 Methods and compositions for treating flaviviruses and pestiviruses
WO2003026589A2 (en) 2001-09-28 2003-04-03 Idenix (Cayman) Limited Methods and compositions for treating hepatitis c virus using 4'-modified nucleosides
AU2003248748A1 (en) 2002-06-28 2004-01-19 Idenix (Cayman) Limited 2'-c-methyl-3'-o-l-valine ester ribofuranosyl cytidine for treatment of flaviviridae infections
RS114104A (en) * 2002-06-28 2007-02-05 Idenix (Cayman) Limited, 2' and 3'-nucleoside prodrugs for treating flaviviridae infections
US7608600B2 (en) 2002-06-28 2009-10-27 Idenix Pharmaceuticals, Inc. Modified 2′ and 3′-nucleoside prodrugs for treating Flaviviridae infections
KR20050088079A (en) 2002-11-15 2005-09-01 이데닉스 (케이만) 리미티드 2'-branched nucleosides and flaviviridae mutation
US7781576B2 (en) 2005-12-23 2010-08-24 Idenix Pharmaceuticals, Inc. Process for preparing a synthetic intermediate for preparation of branched nucleosides

Also Published As

Publication number Publication date
GB1163102A (en) 1969-09-04
CH490367A (en) 1970-05-15
DE1593110A1 (en) 1970-07-16
FR1498856A (en) 1968-01-10
NL6616102A (en) 1967-05-16

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