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9. This substitution pattern is the same as the O-ring of
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26
27. Physical data for 4: ½aꢁD ꢀ47.31 (c 1.00, CHCl3); IR (film)
2951, 1639, 1464, 1379, 1209, 1105, 1039, 984, 913, 865,
816, 747 cmꢀ1; 1H NMR (500 MHz, CDCl3) d 1.26 (3H, s,
Me63), 1.28 (3H, s, Me60), 1.31 (3H, s, Me61), 1.40 (3H, s,
Me), 1.51 (3H, s, Me), 1.65–1.70 (4H, m, H47, 50, 55 · 2),
1.72–1.79 (3H, m, H51 · 2, 54), 1.86–1.93 (2H, m, H50,
54), 2.06 (1H, dd, J = 12.0, 5.0 Hz, H47), 2.41 (1H, ddd,
J = 15.5, 6.5, 4.0 Hz, H43), 2.45 (1H, ddd, J = 15.5, 9.0,
7.0 Hz, H43), 3.33 (3H, s, MOM), 3.49 (1H, dd, J = 9.0,
4.0 Hz, H44), 3.66 (1H, dd, J = 11.0, 5.0 Hz, H49), 3.69
(1H, d, J = 8.5 Hz, H57), 3.88 (1H, dd, J = 12.0, 5.0 Hz,
H46), 3.88 (1H, d, J = 9.0 Hz, H52), 3.93 (1H, d,
J = 8.5 Hz, H57), 4.58 (1H, d, J = 7.0 Hz, MOM), 4.62
(1H, d, J = 7.0 Hz, MOM), 4.76 (1H, d, J = 12.0 Hz,
NAP), 4.86 (1H, d, J = 12.0 Hz, NAP), 5.01 (1H, dd,
J = 10.0, 2.0 Hz, H41), 5.11 (1H, dd, J = 17.0, 2.0 Hz,
H41), 5.93 (1H, dddd, J = 17.0, 10.0, 7.0, 6.5 Hz, H42),
7.43–7.49 (3H, m, NAP), 7.77–7.82 (4H, m, NAP); 13C
NMR (50 MHz, CDCl3) d 14.0, 18.8, 20.4, 24.7, 25.2, 26.9,
27.4, 30.5, 35.2, 37.2, 42.8, 56.0, 72.9, 73.0, 73.8, 74.4, 74.7,
76.2, 77.9, 79.8, 84.6, 95.8, 103.2, 111.2, 116.2, 125.8,
126.0, 126.4, 126.5, 127.8, 127.9, 128.0, 133.0, 133.4, 136.8,
137.4; HRMS (ESI), Anal. Calcd for C36H50NaO8
(M+Na)+ 633.3403, found 633.3401.
11. Compound 6 was derived from 2-D-deoxyribose by
application of Nicolaou’s method (nine steps, 43% yield).
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