2
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6
7
8
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4
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1
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0. (a) Hanessian, S.; Frenette, R. Tetrahedron Lett. 1979,
2
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tion, where the aldehyde was generated in situ, cf.: Han,
Y.; Chorev, M. J. Org. Chem. 1999, 64, 1972–1978.
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24. A representative procedure for tandem reduction–reduc-
tive alkylation of azido sugars: methyl 2-deoxy-2-N-(4-
1
1
ethylenedioxypentyl)-a-1
D
5
-mannopyranoside
(7).
A
mixture of compound 1 (1.07 g, 4.90 mmol), aldehyde 6
(707 mg, 4.90 mmol) and 10% Pd/C (504 mg) was hydro-
1
genated in MeOH (40 mL) under H (40 psi) at rt for
2
27.5 h, and then filtered. The filtrate was concentrated in
vacuo and the residue was purified by flash column
14. Czech, B. P.; Bartsch, R. A. J. Org. Chem. 1984, 49,
4
076–4078.
chromatography (7:1 CHCl
as a clear syrup (1.20 g, 76%): H NMR (400 MHz, D O)
2
3
:MeOH) to give compound 7
1
1
5. Koto, S.; Asami, K.; Hirooka, M.; Nagura, K.; Tak-
izawa, M.; Yamamoto, S.; Okamoto, N.; Sato, M.;
Tajima, H.; Yoshida, T.; Nonaka, N.; Sato, T.; Zen, S.;
Yago, K.; Tomonaga, F. Bull. Chem. Soc. Jpn. 1999, 72,
l 4.81 (d, J=1.1 Hz, 1H), 4.07–3.97 (m, 4H), 3.92 (dd,
J=9.4, 4.7 Hz, 1H), 3.89–3.84 (m, 1H), 3.83–3.76 (m,
1H), 3.63–3.55 (m, 2H), 3.41 (s, 3H), 2.97 (dd, J=4.7, 1.4
Hz, 1H), 2.72 (dt, J=11.8, 7.4 Hz, 1H), 2.55 (dt, J=11.8,
7.4 Hz, 1H), 1.75–1.68 (m, 2H), 1.63–1.52 (m, 2H), 1.37
7
65–777.
1
6. Greene, T. W.; Wuts, P. G. M. Protecive Groups in
Organic Synthesis, 3rd edn; John Wiley & Sons: New
York, 1999.
1
3
(s, 3H); C NMR (100 MHz, D
72.5, 69.3, 67.1 (2C), 63.5, 63.5, 57.5, 50.8, 38.2, 26.0,
O) l 113.3, 101.6, 75.0,
2
+
1
7. Jacquinet, J.-C.; Sinay, P. Carbohydr. Res. 1987, 159,
25.5; HRMS calcd for C14
found 322.1860.
H28NO (M+H) 322.1866,
7
2
29–253.