RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2005(2): 187-192
DOI: 10.1055/s-2004-834941
DOI: 10.1055/s-2004-834941
PAPER
© Georg Thieme Verlag Stuttgart · New York
Improved Synthesis of 1,3-Propanediol Derivatives Having a Diethoxyphosphoryldifluoroethyl Functional Group at the 2-Position: Application to Chemoenzymatic Synthesis of Novel Acyclic Nucleotide Analogues of Adenosine Bisphosphates
Weitere Informationen
Received
7 September 2004
Publikationsdatum:
01. Dezember 2004 (online)
Publikationsverlauf
Publikationsdatum:
01. Dezember 2004 (online)
Abstract
An alternative synthesis of 1,3-propanediol 1 having a diethoxyphosphoryldifluoroethyl group was examined. The method readily provided a multi-gram quantity of 1. The propanediol 1 was chemo-enzymatically transformed to acyclic nucleotide analogues for adenosine bisphosphates.
Key words
1,3-propanediols - fluorine - transesterifications - chiral pool - nucleotide analogues
-
1a
Bornscheuer UT.Kazlauskas RJ. Hydrolases in Organic Synthesis Wily-VCH; Weinheim: 1999. -
1b
Schmidt RD.Verger R. Angew. Chem. Int. Ed. 1998, 37: 1608 -
1c
Stecher H.Faber K. Synthesis 1997, 1 - For recent leading references, see:
-
2a
Burke TR.Ye B.Yan X.Wang S.Jia Z.Chen L.Zhang Z.-Y.Barford D. Biochemistry 1996, 35: 15989 -
2b
Halazy S.Ehrhard A.Eggenspiller A.Berges-Gross V.Danzin C. Tetrahedron 1996, 52: 177 -
2c
Yokomatsu T.Murano T.Umesue I.Soeda S.Shimeno H.Shibuya S. Bioorg. Med. Chem. Lett. 1999, 9: 529 -
2d
Yokomatsu T.Hayakawa Y.Kihara T.Koyanagi S.Soeda S.Shimeno H.Shibuya S. Bioorg. Med. Chem. 2000, 8: 2571 -
2e
Jia Z.Ye Q.Dinaut AN.Wang Q.Waddleton D.Payette P.Ramachandran C.Kennedy B.Hum G.Taylor SD. J. Med. Chem. 2001, 44: 4584 -
2f
Yokomatsu T.Murano T.Akiyama T.Koizumi J.Shibuya S.Tsuji Y.Soeda S.Shimeno H. Bioorg. Med. Chem. Lett. 2003, 13: 229 -
2g
Yokomatsu T.Kato J.Sakuma C.Shibuya S. Synlett 2003, 1407 - 3
Yokomatsu T.Sato M.Shibuya S. Tetrahedron: Asymmetry 1996, 7: 2743 - 4
Boyer JL.Romero-Avila T.Schachter JB.Harden TK. Mol. Pharmacol. 1996, 50: 1323 -
5a
Berkowitz DB.Eggen M.Shen Q.Sloss DG. J. Org. Chem. 1993, 58: 6174 -
5b
Shen Q.Sloss DG.Berkowitz DB. Synth. Commun. 1994, 24: 1519 - 6
Yokomatsu T.Suemune K.Murano T.Shibuya S. J. Org. Chem. 1996, 61: 7207 - 7
Guillarme S.Legoupy S.Bourgougnon N.Aubertin A.-M.Huet F. Tetrahedron 2003, 59: 963 -
8a
Kim HS.Barak D.Harden TK.Boyer JL.Jacobson KA. J. Med. Chem. 2001, 44: 3092 -
8b
Jacobson KA.Jarvis MF.Williams M. J. Med. Chem. 2002, 45: 1 -
8c
Xu B.Stephens A.Kirschenheuter G.Gresline AF.Cheng X.Sennelo J.Cattaneo M.Zighetti ML.Chen A.Kim A.-S.Kim HS.Bischofberger N.Cook G.Jacobson KA. J. Med. Chem. 2002, 45: 5694 ; and references cited therein -
9a
Porritt GM.Reese CB. Tetrahedron Lett. 1989, 30: 4713 -
9b
Uhlmann E.Peyman A. Chem. Rev. 1990, 90: 543 -
9c
Ahmad A. Tetrahedron Lett. 1991, 32: 4483 -
9d
Beaucage LS.Iyer PL. Tetrahedron 1993, 49: 6123 -
9e
Wendeborn S.Jouanno C.Wolf RM.Mesmaeker A. Tetrahedron Lett. 1996, 37: 5511 -
10a
Murano T.Yuasa Y.Muroyama S.Yokomatsu T.Shibuya S. Tetrahedron 2003, 59: 9059 -
10b
Murano T.Yuasa Y.Kobayakawa H.Yokomatsu T.Shibuya S. Tetrahedron 2003, 59: 10223