Abstract
An efficient synthesis of a 2-deoxy-2-acetonyl sugar from its corresponding natural sugar by methallylation of the 2–iodo sugar is reported. The simplified procedure eliminated the need to carry out the reaction under strictly controlled conditions, giving an efficient route for the synthesis of 2-deoxy-2-acetonyl sugar under ordinary laboratory conditions.
References
1.
Prescher J.A.
, and
Bertozzi C.R.
, Cell , 2006 , 126 , 851 .
2.
Kurihara T.
,
Min J.Z.
,
Toyo'oka T.
,
Fukushima T.
, and
Inagaki S.
, Anal. Chem. , 2007 , 79 , 8694 .
3.
Min J.Z.
,
Toyo'oka T.
,
Kawanishi H.
,
Fukushima T.
, and
Kato M.
, Anal. Chim. Acta , 2005 , 550 , 173 .
4.
Rabuka D.
,
Hubbard S.C.
,
Laughlin S.T.
,
Argade S.P.
, and
Bertozzi C.R.
, J. Am. Chem. Soc. , 2006 , 128 , 12078 .
5.
Laughlin S.T.
,
Baskin J.M.
,
Amacher S.L.
, and
Bertozzi C.R.
, Science , 2008 , 320 , 664 .
6.
Yamada K.
,
Hyodo S.
,
Kinoshita M.
,
Hayakawa T.
, and
Kakehi K.
, Anal. Chem. , 2010 , 82 , 7436 .
7.
Prescher J.A.
, and
Bertozzi C.R.
, Nat. Chem. Biol. , 2005 , 1 , 13 .
8.
Khidekel N.
,
Arndt S.
,
Lamarre-Vincent N.
,
Lippert A.
,
Poulin-Kerstien K.G.
,
Ramakrishnan B.
,
Qasba P.K.
, and
Hsieh-Wilson L.C.
, J. Am. Chem. Soc. , 2003 , 125 , 16162 .
9.
Dube D.H.
, and
Bertozzi C.R.
, Curr. Opin. Chem. Biol. , 2003 , 7 , 616 .
10.
Hang H.C.
, and
Bertozzi C.R.
, Acc. Chem. Res , 2001 , 34 , 727 .
11.
Sprung R.
,
Nandi A.
,
Chen Y.
,
Kim S.C.
,
Barma D.
,
Falck J.R.
, and
Zhao Y.
, J. Proteome Res. , 2005 , 4 , 950 .
12.
Mahal L.K.
,
Yarema K.J.
, and
Bertozzi C.R.
, Science , 1997 , 276 , 1125 .
13.
Rexach J.E.
,
Clark P.M.
, and
Hsieh-Wilson L.C.
, Nat. Chem. Biol. , 2008 , 4 , 97 .
14.
Khidekel N.
,
Ficarro S.B.
,
Clark P.M.
,
Bryan M.C.
,
Swaney D.L.
,
Rexach J.E.
,
Sun Y.E.
,
Coon J.J.
,
Peters E.C.
, and
Hsieh-Wilson L.C.
, Nat. Chem. Biol. , 2007 , 3 , 339 .
15.
Hang H.C.
, and
Bertozzi C.R.
, J. Am. Chem. Soc. , 2001 , 123 , 1242 .
16.
Tai H.-C.
,
Khidekel N.
,
Ficarro S.B.
,
Peters E.C.
, and
Hsieh-Wilson L.C.
, J. AM. CHEM. SOC , 2004 , 126 , 10500 .
17.
Lafont D.
, and
Boullanger P.
, Tetrahedron: Asymmetry , 2006 , 17 , 3368 .
18.
Cai L.
,
Guan W.
,
Chen W.
, and
Wang P.G.
, J. Org. Chem , 2010 , 75 , 3492 .
19.
Lafont D.
,
Boullanger P.
, and
Rosenzweig M.
, J. Carbohydr. Chem. , 1998 , 17 , 1377
20.
Gammon D.W.
,
Kinfe H.H.
,
De Vos D.E.
,
Jacobs P.A.
, and
Sels B.F.
, Tetrahedron Lett. , 2004 , 45 , 9533 .
21.
Keck G.E.
,
Enholm E.J.
,
Yates J.B.
, and
Wiley M.R.
, Tetrahedron , 1985 , 41 , 4079 .
22.
Yu W.
,
Mei Y.
,
Kang Y.
,
Hua Z.
, and
Jin Z.
, Org. Lett. , 2004 , 6 , 3217 .
23.
Zhao J.
,
Wei S.
,
Ma X.
, and
Shao H.
, Carbohydr. Res. , 2010 , 345 , 168 .
