Abstract
Silylated 2-(methylsulfanyl)uracils were condensed in the presence of TMS triflate with methyl 2,3-dideoxy-5-O-(4-methylbenzoyl)-D-glycero-pentofuranoside (2) to give, after deprotection, the corresponding nucleosides 6a-f and 7a-f.
References
1.
Barre-Sinoussi
F.
,
Chermann
J.C.
,
Rey
R.
,
Nugeyre
M.T.
,
Chamaret
S.
,
Gruest
C.
,
Dauguet
C.
,
Axler-Blin
C.
,
Vezinet-Brun
Rouzioux F.
,
Rozenbaum
W.
, and
Montagnier
L.
, Science 1983 , 220 , 868 .
2.
Mitsuya
H.
,
Weinhold
K.J.
,
Furman
P.A.
,
Saint-Clair
M.A.
,
Nusinoff
S.
,
Gallo
R.C.
,
Bolognesi
D.
,
Barry
D.W.
, and
Broder
S.
, Proc. Natl. Acad. Sci. U.S.A. 1985 , 82 , 7096 .
3.
Fischl
M.A.
,
Richman
D.D.
,
Gottlieb
M.S.
,
Volberding
P.A.
,
Laskin
O.L.
,
Leedom
J.M.
,
Groopman
J.E.
,
Mildvan
D.
,
Schooley
R.T.
,
Jackson
G.G.
,
Durack
D.T.
,
King
D.
, and
Engl
N.
, J. Med. Chem. 1987 , 317 , 185 .
4.
Richman
D.D.
,
Fischl
M.A.
,
Go Hlieb
M.S.
,
Volberding
P.A.
,
Laskin
O.L.
,
Leedom
J.M.
,
Groopman
J.E.
,
Mildvan
D.
,
Hie Sch
M.S.
,
Jackson
G.G.
,
Durack
D.T.
,
Nusinoff Lehrman
S.
, and
Engl
N.
, J. Med. Chem. 1987 , 317 , 192 .
5.
De Clercq
E.
, Anticancer Res. 1987 , 7 , 1023 .
6.
Broder
S.
, Pharm. Technol. 1988 , 12 , 24 .
7.
Abdel-Rahman
A.A.-H.
,
Abdel-Barry
H.M.
,
Pedersen
E.B.
, and
Nielsen
C.
, Arch. Pharm. 1995 , 328 , 67 .
8.
Abdel-Rahman
A.A.-H.
,
Zahran
M.A.
,
Abdel-Megied
A.E.-S.
,
Pedersen
E.B.
, and
Nielsen
C.
, Synthesis 1996 , 237 .
9.
Zahran
M.A.
,
Abdel-Megied
A.E.-S.
,
Abdel-Rahman
A.A.-H.
,
El-Emam
A.
,
Pedersen
E.B.
, and
Nielsen
C.
, Heterocycles 1995 , 41 , 2507 .
10.
Zahran
M.A.
,
Abdel-Megied
A.E.-S.
,
Abdel-Rahman
A.A.-H.
,
Sofan
M.A.
,
Pedersen
E.B.
, and
Nielsen
C.
, Monatsh. Chem. 1996 , 127 , 979 .
11.
Abdel-Rahman
A.A.-H.
, Afinidad 1997 , 54 , 135 .
12.
Abdel-Rahman
A.A.-H.
, and
Abdel-Aal
M.T.
, Pharmazie 1998 , 53 , 377 .
13.
Zeid
I.F.
,
Abdel-Rahman
A.A.-H.
,
Abdel-Megied
A.E.-S.
, and
El-Etrawy
A.SH.
, Nucleosides Nucleotides 1999 , 18 , 95 .
14.
Abdel-Rahman
A.A.-H.
, Pharmazie in press.
15.
Brown
T.H.
,
Blakemore
R.C.
,
Emmett
G.J.
,
Robin
G.C.
,
Parsons
M.E.
,
Anthony
D.A.
, and
Walker
T.F.
, Eur. J. Med. Chem. 1988 , 23 , 53 .
16.
Vorbrüggen
H.
,
Krolikiewicz
K.
, and
Bennua
B.
, Chem. Ber. 1981 , 114 , 1234 .
17.
Niedballa
U.
, and
Vorbrüggen
H.
, J. Org. Chem. 1974 , 39 , 3654 .
18.
Wilson
L.J.
, and
Liotta
D.
, Tetrahedron Lett. 1990 , 31 , 1815 .
19.
Rosemeyer
H.
,
Toth
G.
,
Golankiewicz
B.
,
Kazimierczuk
Z.
,
Bourgeois
W.
,
Kretschmer
U.
,
Muth
H.P.
, and
Seela
F.
, J. Org. Chem. 1990 , 55 , 5784 .
20.
El-Barbary
A.A.
,
El-Brollosy
N.R.
,
Pedersen
E.B.
, and
Nielsen
C.
, Sulfur Lett. 1996 , 20 , 31 .
