Abstract
Herein, we present the synthesis of three new 2-azido-2-deoxy-d -mannopyranose building blocks that are
useful in the preparation of oligosaccharides consisting of α(1→4)-linked
2-azido-2-deoxy-d -mannopyranose units.
The successful utilization of these intermediates in the stepwise
synthesis of the corresponding trisaccharide is also described in
detail.
Key words
carbohydrates - glycosylation - oligosaccharides -
d -mannosamine
References <A NAME="RT01808SS-1">1 </A>
Present address: Center for Sustainable
and Green Chemistry, Department of Chemistry, Building 201, Technical
University of Denmark, 2800 Kgs. Lyngby, Denmark.
<A NAME="RT01808SS-2">2 </A>
Dwek RA.
Chem.
Rev.
1996,
96:
683
<A NAME="RT01808SS-3">3 </A>
Varki A.
Glycobiology
1993,
3:
97
<A NAME="RT01808SS-4">4 </A>
Bongat AFG.
Demchenko AV.
Carbohydr.
Res.
2007,
342:
374
<A NAME="RT01808SS-5">5 </A>
Banoub J.
Boullanger P.
Lafont D.
Chem.
Rev.
1992,
92:
1167
<A NAME="RT01808SS-6">6 </A>
Gridley JJ.
Osborn HMI.
J. Chem.
Soc., Perkin Trans. 1
2000,
10:
1471
<A NAME="RT01808SS-7">7 </A>
Veselý J.
Ledvina M.
Jindøich J.
Trnka T.
Šaman D.
Collect.
Czech. Chem. Commun.
2004,
69:
1914
<A NAME="RT01808SS-8">8 </A>
Beynon LM.
Richards JC.
Perry MB.
Kniskern PJ.
Can.
J. Chem.
1992,
70:
218
<A NAME="RT01808SS-9">9 </A>
Osa Y.
Kaji E.
Takahashi K.
Hirooka M.
Zen S.
Lichtenthaler FW.
Chem. Lett.
1993,
1567
<A NAME="RT01808SS-10">10 </A>
Silipo A.
Molinaro A.
Lanzetta R.
Parrilli M.
Lindner B.
Holst O.
Eur. J. Org. Chem.
2004,
1336
<A NAME="RT01808SS-11">11 </A>
Litjens REJN.
Leeuwenburgh MA.
van der Marel GA.
van Boom JH.
Tetrahedron
Lett.
2001,
42:
8693
<A NAME="RT01808SS-12">12 </A>
Litjens REJN.
van den Bos LJ.
Codée JDC.
van den Berg RJBHN.
Overkleeft HS.
van der Marel GA.
Eur.
J. Org. Chem.
2005,
918
<A NAME="RT01808SS-13">13 </A>
van den Bos LJ.
Duivenvoorden BA.
de Koning MC.
Filippov DV.
Overkleeft HS.
van der Marel GA.
Eur. J.
Org. Chem.
2007,
116
<A NAME="RT01808SS-14">14 </A>
Crich D.
Chandrasekera NS.
Angew. Chem.
Int. Ed.
2004,
43:
5386
<A NAME="RT01808SS-15">15 </A>
Veselý J.
Rohlenová A.
Dý˛oganová M.
Trnka T.
Tišlerová I.
Šaman D.
Ledvina M.
Synthesis
2006,
699
<A NAME="RT01808SS-16">16 </A>
Schmidt RR.
Kinzy W.
Adv. Carbohydr. Chem. Biochem.
1994,
50:
21
<A NAME="RT01808SS-17">17 </A>
Gin D.
J.
Carbohydr. Chem.
2002,
21:
645
<A NAME="RT01808SS-18">18 </A>
Tanaka H.
Kawai K.
Fujiwara K.
Murai A.
Tetrahedron
2002,
58:
10017
<A NAME="RT01808SS-19">19 </A>
Jenkins DJ.
Potter BVL.
Carbohydr.
Res.
1994,
265:
145
<A NAME="RT01808SS-20">20 </A>
Codée JDC.
van den Bos LJ.
Litjens REJN.
Overkleeft HS.
van Boeckel CAA.
van Boom JH.
van der Marel GA.
Tetrahedron
2004,
60:
1057
<A NAME="RT01808SS-21">21 </A>
Gattuso G.
Nepogodiev SA.
Stoddart JF.
Chem. Rev.
1998,
98:
1919
<A NAME="RT01808SS-22">22 </A>
Hofman-Bang N.
Acta
Chem. Scand.
1957,
11:
581
<A NAME="RT01808SS-23">23 </A>
Jenkins DJ.
Potter BVL.
Carbohydr.
Res.
1996,
287:
169
<A NAME="RT01808SS-24">24 </A>
Holme KR.
Hall LD.
Carbohydr. Res.
1992,
225:
291
<A NAME="RT01808SS-25">25 </A>
Fukase K.
Matsumoto T.
Ito N.
Yoshimura T.
Kotani S.
Kusumoto S.
Bull. Chem. Soc. Jpn.
1992,
65:
2643
<A NAME="RT01808SS-26">26 </A>
Peer A.
Vasella A.
Helv. Chim. Acta
1999,
82:
1044