References and Notes
1a
Sialic Acids: Chemistry, Metabolism and Function
Vol. 10:
Schauer R.
Springer;
New
York:
1982.
1b
Biology
of Sialic Acid
Rosenberg A.
Plenum
Press;
New York:
1995.
1c
Traving C.
Schauer R.
Cell. Mol. Life Sci.
1998,
54:
1330
1d
Lehmann F.
Tiralongo E.
Tiralongo J.
Cell.
Mol. Life Sci.
2006,
63:
1331
For reviews, see:
2a
Okamoto K.
Goto T.
Tetrahedron
1990,
46:
5835
2b
Boons G.-J.
Demchenko AV.
Chem. Rev.
2000,
100:
4539
2c
Hasegawa A.
Kiso M. In
Preparative
Carbohydrate Chemistry
Hanessian S.
Marcel
Dekker;
New York:
1997.
p.357
For recent examples, see:
3a
Ando H.
Koike Y.
Ishida H.
Kiso M.
Tetrahedron Lett.
2003,
44:
6883
3b
Matsuoka K.
Onaga T.
Mori T.
Sakamoto J.-I.
Koyama T.
Sakairi N.
Hatano K.
Terunuma D.
Tetrahedron Lett.
2004,
45:
9383
4a
Marra A.
Sinaÿ P.
Carbohydr.
Res.
1990,
195:
303
4b
Martichonok V.
Whitesides GM.
J. Org. Chem.
1996,
61:
1702
5a
Martin TJ.
Schmidt RR.
Tetrahedron Lett.
1992,
33:
6123
5b
Kondo H.
Ichikawa Y.
Wong CH.
J.
Am. Chem. Soc.
1992,
114:
8748
6
Yu B.
Cai S.
Org. Lett.
2003,
5:
3827
7
Yoshida M.
Uchimura A.
Kiso M.
Hasegawa A.
Glycoconjugate J.
1993,
10:
3
8
Zhang Z.
Niikura K.
Huang X.-F.
Wong C.-H.
Can. J. Chem.
2002,
80:
1051
9
Nagao Y.
Nekado T.
Ikeda K.
Achiwa K.
Chem. Pharm. Bull.
1995,
43:
1536
10
Crich D.
Li W.
Org. Lett.
2006,
8:
959
11
Crich D.
Wu B.
Tetrahedron
2008,
64:
2042
12a
Ito Y.
Ogawa T.
Tetrahedron
1990,
46:
89
12b
Hossain N.
Magnusson G.
Tetradron Lett.
1999,
40:
2217
13 For recent review, see: De
Meo C.
Priyadarshani U.
Carbohydr.
Res.
2008,
343:
1540
14
Crich D.
Li W.
J. Org. Chem.
2007,
72:
2387
15
Crich D.
Li W.
J. Org. Chem.
2007,
72:
7794
16
Farris MD.
De Meo C.
Tetrahedron Lett.
2007,
48:
1225
17
Tanaka H.
Nishiura Y.
Takahashi T.
J.
Am. Chem. Soc.
2006,
128:
7124
18a
Cao S.
Meunier SJ.
Andersson FO.
Letellier M.
Roy R.
Tetrahedron: Asymmetry
1994,
5:
2303
18b
Ye
X.-S.
Huang X.-F.
Wong C.-H.
Chem.
Commun.
2001,
974
18c
Lin C.-C.
Huang K.-T.
Lin C.-C.
Org.
Lett.
2005,
7:
4169
19
Roy R.
Andersson FO.
Letellier M.
Tetrahedron
Lett.
1992,
33:
6053
20
Yu C.-S.
Niikura K.
Lin C.-C.
Wong C.-H.
Angew. Chem. Int. Ed.
2001,
40:
2900
21 Donor 1 was
prepared similarly as literature described.
[¹4]
Compound
characterization data for 5: ¹H
NMR (500 MHz, CD3OD): δ = 7.47 (d, J = 7.7 Hz,
2 H), 7.22 (d, J = 7.7
Hz, 2 H), 4.06 (dt, J = 11.9,
3.3 Hz, 1 H), 3.83 (m, 3 H), 3.67-3.69 (m, 2 H), 3.67 (s,
3 H), 3.55 (d, J = 8.8
Hz, 1 H), 3.14 (dd, J = 11.7,
3.6 Hz, 1 H, H-3eq), 2.38 (s, 3 H), 2.21 (t, J = 12.2
Hz, 1 H, H-3ax). ¹³C-APT NMR (125 MHz, CD3OD): δ = 169.1,
160.9, 140.5, 136.3, 129.3, 125.1, 87.8, 78.3, 78.2, 71.5, 70.0,
63.1, 57.1, 52.2, 36.6, 19.9. HRMS: m/z calcd
for C18H23NO8SNa [M + Na]+:
436.10421; found. 436.10364.
Compound 1: ¹H
NMR (500 MHz, CDCl3): δ = 7.45 (d, J = 7.9 Hz,
2 H), 7.18 (d, J = 7.9
Hz, 2 H), 5.55 (d, J = 5.8 Hz,
1 H), 5.38 (m, 1 H), 4.45 (dd, J = 12.2,
2.6 Hz, 1 H), 4.36 (d, J = 9.4
Hz, 1 H), 4.23 (m, 1 H), 3.98 (m, 1 H), 3.65 (s, 3 H), 3.63 (m,
1 H), 3.10 (dd, J = 12.1,
3.5 Hz, 1 H, H-3eq), 2.48 (s, 3 H), 2.39 (s, 3 H), 2.19 (s, 3 H),
2.14 (m, 1 H, H-3ax), 2.11 (s, 3 H), 2.10 (s, 3 H). ¹³C-APT
NMR (125 MHz, CDCl3): δ = 171.9, 170.6,
170.3, 170.0, 168.2, 153.4, 140.6, 136.3, 129.7, 124.7, 87.8, 77.4,
75.7, 72.6, 70.7, 62.5, 59.1, 53.1, 36.5, 24.7, 21.3, 21.1, 20.9,
20.8. HRMS: m/z calcd for C26H31NO12SNa [M + Na]+:
604.14647; found. 604.14590.
22
General Sialylation
Procedure (with the Coupling Between 1 and 6 as Example)
To
a mixture of donor 1 (40.0 mg, 0.07 mmol,
1.0 equiv), acceptor 6 (38.4 mg, 0.08 mmol,
1.2 equiv), and activated 4 Å powdered MS, was added anhyd
CH2Cl2-MeCN (2:1, 3 mL). The resulted
solution was stirred for 0.5 h at r.t. under Ar, and then cooled
to -40 ˚C followed by addition of NIS (37.7 mg,
0.17 mmol, 2.4 equiv) and TfOH (6.0 µL, 0.07 mmol, 1.0
equiv). The reaction was stirred at -40 ˚C for
1 h. After quenched with Et3N (0.1 mL), the mixture was
diluted with CH2Cl2, filtered through Celite,
washed with 20% aq Na2S2O3 solution,
dried over Na2SO4, and concentrated under
reduced pressure. The residue was purified by column chromatography
on SiO2 eluting with hexane-EtOAc system to
give the coupling product.
23 Compound 17: ¹H
NMR (500 MHz, CDCl3): δ = 5.60 (d, J = 7.2 Hz,
1 H), 5.40 (dt, J = 6.9,
2.8 Hz, 1 H), 5.34 (d, J = 3.1
Hz, 1 H), 5.12 (m, 1 H), 4.55 (d, J = 9.4
Hz, 1 H), 4.42-4.33 (m, 2 H), 4.13 (m, 1 H), 4.01 (m, 1
H), 3.79 (s,
3 H), 3.71 (t, J = 9.8
Hz, 1 H), 3.62 (m, 1 H), 3.48-3.35 (m, 2 H), 2.90 (dd, J = 12.0,
3.2 Hz, 1 H, H-3eq), 2.49 (s, 3 H), 2.15 (s, 3 H), 2.12 (s, 3 H),
2.03 (s, 3 H), 1.01 (s, 3 H), 0.96 (d, J = 6.9
Hz, 3 H), 0.79 (s, 3 H), 0.78 (d, J = 5.7
Hz, 3 H).
24 CCDC 693369 contains the supplementary
crystallographic data for this paper. These data can be obtained
free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.