196 Letters in Organic Chemistry, 2009, Vol. 6, No. 3
Khan et al.
Methyl 2,3,6-tri-O-benzoyl -4-deoxy-ꢀ-D-threo-hex-3-
enopyranosides (42, C28H24O8)
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Starting with 0.661, 0.570, 0.617 g (1 mmol) of 39, 40,
41 after completion of reaction in 3 h (TLC analysis) and
column chromatography (ethyl acetate/hexane) pure 42 was
collected as liquid. Yields 0.595 g (90%), 0.502 g (88%),
0.595 g (90%) from compounds 39, 40, and 41, respectively;
Liquid, [ꢀ]25D = - 1.4 (CHCl3, c = 1.1), (lit. - 1.6) (CHCl3, c =
1.1) [29]; 1H NMR (250 MHz, CDCl3): ꢀ = 3.34 (d, J2,1 = 2.0
Hz, H-2), 3.54 (dd, J6,5 = 5.6, J6,6’ = 9.5 Hz, H-6), 3.57 (s,
OCH3), 3.70 (dd, J6’,5 = 6.1, J6’,6 = 9.5 Hz, H-6’), 4.11 (dd,
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a) Ferrier, R.J.; Sankey, G.H. J. Chem. Soc., (C), 1966, 2339; b)
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J5,4 = 1.6, J5,6 = 5.6 Hz, H-5), 4.51 (d, J1,2 = 2.0 Hz, H-1),
4.91 (d, J4,5 = 1.6 Hz, H-4) ppm; 13C NMR (63 MHz,
CDCl3): ꢀ = 59.1 (OCH3), 61.5 (C-6), 66.6 (C-2), 73.9 (C-5),
98.3 (C-4), 101.4 (C-1), 128.5, 128.8, 129.0, 129.1, 133.4,
(Ph), 152.3 (C-3), 165.3, 165.4, 166.1 (PhCOO) ppm; MS-
EI: m/z (%) = 488 (47) [M+], 473 (51), 457 (74), 411 (100),
383 (66), 367 (89), 246 (55).
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Methyl 3,6-di-O-benzoyl-2-acetamido-2,4-dideoxy-ꢀ-D-
threo-hex-3-enopyranosides (46, C23H23O7N)
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Starting with 0.598, 0.507, 0.554 g (1 mmol) of 43, 44,
45 after completion of reaction in 3 h (TLC analysis) and
column chromatography (ethyl acetate/hexane) pure 46 was
collected as liquid. Yields 0.538 g (90%), 0.431 g (85%),
0.482 g (87%) from compounds 43, 44, and 45, respectively;
Liquid, [ꢀ]25D = + 2.0 (CHCl3, c = 1.1), (lit. + 2.1) (CHCl3, c
= 1.1) [29]; 1H NMR (250 MHz, CDCl3): ꢀ = 2.01 (s,
COCH3), 2.91 (d, J2,1 = 1.8 Hz, H-2), 3.01 (s, NH), 3.51 (dd,
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a) Ferrier, R.J.; Prasit, P. J. Chem. Soc. Chem. Commun., 1981,
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Blair, M.G. Methods Carbohydr., 1963, 2, 415.
J6,5 = 5.1, J6,6’ = 9.8 Hz, H-6), 3.58 (s, OCH3), 3.60 (dd, J6’,5 =
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6.0, J6’,6 = 9.8 Hz, H-6’), 3.89 (dd, J5,4 = 1.8, J5,6’ = 6.0 Hz, H-
5), 4.59 (d, J1,2 = 1.8 Hz, H-1), 4.88 (d, J4,5 = 1.8 Hz, H-4)
ppm; 13C NMR (63 MHz, CDCl3): ꢀ = 61.6 (C-6), 56.4 (C-
2), 73.9 (C-5), 97.3 (C-4), 100.4 (C-1), 128.4, 129.2, 129.3,
129.3, 133.7, (Ph), 152.5 (C-3), 165.1, 166.1 (PhCOO) ppm;
MS-EI: m/z (%) = 425 (32) [M+], 410 (69), 394 (51), 382
(78), 367 (38), 348 (41), 336 (28), 320 (49), 304 (100), 290
(17).
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Methyl 2,3,6-tri-O-benzoyl-4-deoxy-ꢀ-D-threo-hex-3-
enopyranosides (50, C28H24O8)
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Jain, S.; Suryawanshi, S.N.; Misra, S.; Bhakuni, D.S. Indian J.
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Starting with 0.661, 0.570, 0.617 g (1 mmol) of 47, 48,
49 after a reaction time of 4 h and column chromatography
(ethyl acetate/hexane) pure 50 was collected as liquid. Yields
0.602 g (91%), 0.485 g (85%), 0.490 g (86%) from com-
pounds 47, 48, and 49 respectively; Liquid, [ꢀ]25D = + 2.6
(CHCl3, c = 1); 1H NMR (250 MHz, CDCl3): ꢀ = 3.24 (d, J2,1
= 3.5 Hz, H-2), 3.43 (dd, J6,5 = 6.1, J6,6’ = 9.5 Hz, H-6), 3.55
(s, OCH3), 3.62 (dd, J6’,5 = 6.6, J6’,6 = 9.5 Hz, H-6’), 4.11 (dd,
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J
5,4 = 2.4, J5,6 = 6.1 Hz, H-5), 4.75 (d, J1,2 = 3.5 Hz, H-1),
4.91 (d, J4,5 = 2.4 Hz, H-4) ppm; 13C NMR (63 MHz,
CDCl3): ꢀ = 59.2 (OCH3), 61.7 (C-6), 66.4 (C-2), 73.7 (C-5),
96.7 (C-4), 102.2 (C-1), 128.3, 128.6, 129.1, 129.0, 133.2
(Ph), 151.3 (C-3), 165.1, 165.2, 166.3 (PhCOO) ppm; MS-
EI: m/z (%) = 488 (36) [M+], 473 (43), 457 (84), 411 (100),
383 (57), 367 (71), 246 (42).
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ACKNOWLEDGEMENT
Dr. Khalid Mohammed Khan and Dr. Shahnaz Perveen
are thankful to Deutscher Akademischer Austauschdienst
(DAAD, Bonn, Germany) for a short term scholarship.