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Volumn 54, Issue 28, 1998, Pages 8171-8182

A versatile procedure for the generation of nucleoside 5'- carboxylic acids using nucleoside oxidase

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; NUCLEOSIDE; NUCLEOSIDE 5 CARBOXYLIC ACID; OXIDOREDUCTASE; UNCLASSIFIED DRUG;

EID: 0032499993     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00456-6     Document Type: Article
Times cited : (16)

References (16)
  • 2
    • 85038533251 scopus 로고    scopus 로고
    • US Pat. Appl. 5,156,955, 1992
    • 2. Isono, Y.; Hoshino, M. US Pat. Appl. 5,156,955, 1992.
    • Isono, Y.1    Hoshino, M.2
  • 6
    • 85038529481 scopus 로고    scopus 로고
    • Compounds 13 & 14 were synthesised from 8 in 4 steps: the 3′-OH/5′-OH TIPS protection of 8 using dichlorotetraisopropylsiloxane in pyridine, followed by oxidation of the 2′ hydroxyl group to the ketone using Moffatt conditions (DCC/orthophosphoric acid in DMSO), reaction with methylmagnesium iodide in diethyl ether and separation of the diastereomeric mixture of tertiary alcohols and finally deprotection using potassium fluoride dihydrate/18-crown-6 in THF
    • 6. Compounds 13 & 14 were synthesised from 8 in 4 steps: the 3′-OH/5′-OH TIPS protection of 8 using dichlorotetraisopropylsiloxane in pyridine, followed by oxidation of the 2′ hydroxyl group to the ketone using Moffatt conditions (DCC/orthophosphoric acid in DMSO), reaction with methylmagnesium iodide in diethyl ether and separation of the diastereomeric mixture of tertiary alcohols and finally deprotection using potassium fluoride dihydrate/18-crown-6 in THF.
  • 7
    • 85038528360 scopus 로고    scopus 로고
    • Eur. Pat. Appl., EP 139358, 1985
    • 7. For the synthesis of 1 see; Bristol, J.A.; Trivedi, B.; Moos, W.H. Eur. Pat. Appl., EP 139358, 1985 & Ayres, B.E.; Gregson, M.; Ewan, G.B.; Keeling, S.E.; Bell, R. PCT Int. Appl., WO 9602553, 1996.
    • Bristol, J.A.1    Trivedi, B.2    Moos, W.H.3
  • 8
    • 85038529007 scopus 로고    scopus 로고
    • PCT Int. Appl., WO 9602553, 1996
    • 7. For the synthesis of 1 see; Bristol, J.A.; Trivedi, B.; Moos, W.H. Eur. Pat. Appl., EP 139358, 1985 & Ayres, B.E.; Gregson, M.; Ewan, G.B.; Keeling, S.E.; Bell, R. PCT Int. Appl., WO 9602553, 1996.
    • Ayres, B.E.1    Gregson, M.2    Ewan, G.B.3    Keeling, S.E.4    Bell, R.5
  • 10
    • 0016789550 scopus 로고    scopus 로고
    • Eur. Pat. Appl., EP 323807, 1989
    • 8. For the synthesis of 4 see; Marumoto, R.; Yoshioka, Y.; Miyashita, O.; Shima, S.; Imai, K.; Kawazoe, K.; Honjo, M. Chem. Pharm. Bull. 1975, 23, 759-74 & Hutchison, A.J.; Francis, J.E. Eur. Pat. Appl., EP 323807, 1989.
    • Hutchison, A.J.1    Francis, J.E.2
  • 11
    • 85038533401 scopus 로고    scopus 로고
    • Adenosine N-oxide (5), was obtained from Sigma
    • 9. Adenosine N-oxide (5), was obtained from Sigma.
  • 12
    • 85038531093 scopus 로고    scopus 로고
    • 2-Methylinosine (7) was synthesised in one step from 5-amino-1-β-D-ribofuranosyl-4-imidazolecarboxamide using the method of Ajinomoto Co., Inc. Neth. Appl., NL 6600317, 1966
    • 10.2-Methylinosine (7) was synthesised in one step from 5-amino-1-β-D-ribofuranosyl-4-imidazolecarboxamide using the method of Ajinomoto Co., Inc. Neth. Appl., NL 6600317, 1966.
  • 13
    • 0025817398 scopus 로고
    • 11. Methyl isoguanosine (6) was synthesised in one step from 5-amino-1-β-D-ribofuranosyl-4-imidazolecarboxamide using the method of Chem, J. W.; Lin, G. S.; Chen, C. S.; Townsend, L. B. J. Org. Chem. 1991, 56, 4213-18.
    • (1991) J. Org. Chem. , vol.56 , pp. 4213-4218
    • Chem, J.W.1    Lin, G.S.2    Chen, C.S.3    Townsend, L.B.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.