메뉴 건너뛰기




Volumn 16, Issue 10, 2008, Pages 5424-5433

Synthesis of 5′-functionalized nucleosides: S-Adenosylhomocysteine analogues with the carbon-5′ and sulfur atoms replaced by a vinyl or halovinyl unit

Author keywords

Cross coupling; Cross metathesis; Nucleosides; S Adenosylhomocysteine hydrolase; Wittig reaction

Indexed keywords

5' DEOXY 5' (IODOMETHYLENE)NUCLEOSIDE; 5' DEOXY 5' METHYLENEADENOSINE; ADENOSINE DERIVATIVE; ADENOSYLHOMOCYSTEINASE; ALKENYL GROUP; AMINO ACID DERIVATIVE; BROMINE DERIVATIVE; FLUORINE DERIVATIVE; NUCLEOSIDE DERIVATIVE; PALLADIUM; S ADENOSYLHOMOCYSTEINE; URIDINE DERIVATIVE; VINYL DERIVATIVE; ZINC DERIVATIVE; CARBON; NUCLEOSIDE; SULFUR;

EID: 43749117513     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.04.017     Document Type: Article
Times cited : (9)

References (62)
  • 24
    • 34250756119 scopus 로고    scopus 로고
    • For recent examples on the importance and synthetic challenges associated with the synthesis of the uracil-nucleosides functionalized at C5′ see:
    • For recent examples on the importance and synthetic challenges associated with the synthesis of the uracil-nucleosides functionalized at C5′ see:. Zhang X., Bernet B., and Vasella A. Helv. Chim. Acta 90 (2007) 864
    • (2007) Helv. Chim. Acta , vol.90 , pp. 864
    • Zhang, X.1    Bernet, B.2    Vasella, A.3
  • 35
    • 20544443728 scopus 로고    scopus 로고
    • For application of metathesis towards synthesis of nucleoside analogues see:
    • For application of metathesis towards synthesis of nucleoside analogues see:. Amblard F., Nolan S.P., and Agrofoglio L.A. Tetrahedron 61 (2005) 7067
    • (2005) Tetrahedron , vol.61 , pp. 7067
    • Amblard, F.1    Nolan, S.P.2    Agrofoglio, L.A.3
  • 38
    • 0042770306 scopus 로고    scopus 로고
    • For an example on self-metathesis reaction of carbohydrate derived terminal olefins (e.g., 5,6-dideoxy-1,2-O-isopropylidene-α-d-ribo-hex-5-enofuranose) see:
    • For an example on self-metathesis reaction of carbohydrate derived terminal olefins (e.g., 5,6-dideoxy-1,2-O-isopropylidene-α-d-ribo-hex-5-enofuranose) see:. Hadwiger P., and Stütz A.E. Synlett (1999) 1787
    • (1999) Synlett , pp. 1787
    • Hadwiger, P.1    Stütz, A.E.2
  • 41
    • 43749107556 scopus 로고    scopus 로고
    • note
    • Attempted metathesis of uridine precursor 3 with 4a or 4b in the presence of Hoveyda-Grubb's catalyst failed to give products 5a or 5c. It seems that 2nd generation Grubbs catalyst is more compatible with pyrimidine bases, while Hoveyda-Grubbs catalyst gave better results with purine nucleosides.
  • 42
    • 20544450502 scopus 로고    scopus 로고
    • de Meijere A., and Diederich F. (Eds), Wiley-VCH, Weinheim, Germany
    • In: de Meijere A., and Diederich F. (Eds). Metal-Catalyzed Cross-Coupling Reactions (2004), Wiley-VCH, Weinheim, Germany
    • (2004) Metal-Catalyzed Cross-Coupling Reactions
  • 44
  • 47
    • 43749100461 scopus 로고    scopus 로고
    • 5a,18) produced desired 11a and 12a in low and irreproducible yields (∼5-20%).
    • 5a,18) produced desired 11a and 12a in low and irreproducible yields (∼5-20%).
  • 49
    • 43749101144 scopus 로고    scopus 로고
    • 26b was unsuccessful.
    • 26b was unsuccessful.
  • 52
    • 31444443317 scopus 로고    scopus 로고
    • For studies on differentiation of two chlorine atoms in stepwise double alkylation reactions of 1,1-dichloroalkenes see:
    • For studies on differentiation of two chlorine atoms in stepwise double alkylation reactions of 1,1-dichloroalkenes see:. Tan Z., and Negishi E.-I. Angew. Chem., Int. Ed. 45 (2006) 762
    • (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 762
    • Tan, Z.1    Negishi, E.-I.2
  • 53
    • 33947210187 scopus 로고    scopus 로고
    • For Suzuki-Miyaura protocol to the selective monocoupling of 1,1-dichloroalkenes with 9-alkyl-9-BBN see:
    • For Suzuki-Miyaura protocol to the selective monocoupling of 1,1-dichloroalkenes with 9-alkyl-9-BBN see:. Liron F., Fosse C., Pernolet A., and Roulland E. J. Org. Chem. 72 (2007) 2220
    • (2007) J. Org. Chem. , vol.72 , pp. 2220
    • Liron, F.1    Fosse, C.2    Pernolet, A.3    Roulland, E.4
  • 54
    • 43749124647 scopus 로고    scopus 로고
    • 28b (which also has an oxygen atom at the γ-carbon from the halovinyl unit) also produced E/Z mixture of the coupling products.
    • 28b (which also has an oxygen atom at the γ-carbon from the halovinyl unit) also produced E/Z mixture of the coupling products.
  • 56
    • 43749101641 scopus 로고    scopus 로고
    • note
    • 11,28b byproducts.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.