7310
S. P. Chavan et al. / Tetrahedron Letters 45 (2004) 7307–7310
2993/1/245; Goodness-of-fit on F2 = 1.097, final R indices
[I > 2sigma(I)] = R1 = 0.0362, wR2 = 0.0932, R indices (all
data) = R1 = 0.0366, wR2 = 0.0936, absolute structure para-
meter = ꢀ0.1(8), largest diff. peak and hole = 0.185 and
acknowledged. We are thankful to Green Chem.
Bangalore for a generous supply of D-glucosamine
hydrochloride.
ꢀ3
˚
ꢀ0.257eA
.
Additional
crystallographic
details
References and notes
CCDC243900 (atomic co-ordinates and equivalent iso-
tropic displacement coefficients) have been deposited at the
Cambridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB2 1EZ, UK.
1. For a recent review on biotin see: (a) DeClercq, P. J. Chem.
Rev. 1997, 97, 1755–1792; (b) Senuma, M.; Fujii, T.;
Okamu, K.; Date, T.; Kinumaki, A. Chem. Pharm. Bull.
1990, 38, 882–887; (c) Iriuchijuma, S.; Hasegawa, K.;
Tsuchihashi, G. Agric. Biol. Chem. 1982, 46, 1907–1910.
2. (a) Ravindranathan, T.; Hiremath, S. V.; Reddy, D. R.;
Rama Rao, A. V. Carbohydr. Res. 1984, 134, 332–336; (b)
Ohuri, H.; Emoto, S. Tetrahedron Lett. 1975, 2765–2766;
(c) Ogawa, T.; Kawano, T.; Matsui, M. Carbohydr. Res.
1977, 57, C31–C35; (d) Ohuri, H.; Sueda, N.; Emoto, S.
Agric. Biol. Chem. 1978, 42, 865–867; (e) Vogel, F. G. M.;
Paust, J.; Nurrenbach, A. Liebigs Ann. Chem. 1980,
1972–1975.
3. (a) Poesch, E.; Casutt, M. Chimia 1987, 41, 148–150; (b)
Fusijawa, T.; Nagai, M.; Kaike, Y.; Shimizu, M. J. Org.
Chem. 1994, 59, 5865–5867; (c) Deroose, F. D.; De Clercq,
P. J. J. Org. Chem. 1995, 60, 321–330; (d) Moolenaer, M. J.;
Speckamp, W. N.; Hiemstra, H.; Poetsch, E.; Casutt, M.
Angew. Chem., Int. Ed. Engl. 1995, 34, 2391–2392; (e)
Chavan, S. P.; Tejwani, B.; Ravindranathan, T. J. Org.
Chem. 2001, 66, 6197–6201.
7. Crystal data of compound 7: C30H29N3O5; M = 511.56,
˚
space group = 0 Monoclinic, P2(1), a = 12.1575(18)A,
˚
˚
b = 7.5820(11)A, c = 15.312(2)A·. a = 90ꢁ. b = 92.297(2)ꢁ,
c = 90ꢁ, V = 1410.3(4)A , Dc = 2, 1.205Mg/m3, (Mo-
3
˚
Ka) = 0.083mmꢀ1
,
F(000) = 540; crystal = 0.75 · 0.28 ·
0.16mm; theta range for data collection 1.68–26.00ꢁ,
limiting = ꢀ14 6 h 6 14, ꢀ9 6 k 6 9, ꢀ17 6 l 6 18; reflec-
tions collected/unique 11003/5391 [R(int) = 0.0231]; com-
pleteness to theta = 26.00, 99.6%, absorption correction
semi-empirical from equivalents; max. and min. = 0.9869
and 0.9405, refinement method = full-matrix least-squares
on F2; data/restraints/parameters 5391/1/344; goodness-
of-fit on F2 = 1.078, final
R1 = 0.0493, wR2 = 0.1179;
R
R
indices [I > 2sigma(I)]
indices (all data) =
R1 = 0.0598, wR2 = 0.1242, absolute structure parame-
ter = ꢀ1.1(11), Largest diff. peak and hole = 0.137and
ꢀ3
˚
ꢀ0.110eA
.
Additional
crystallographic
details
CCDC243901 (atomic co-ordinates and equivalent
isotropic displacement coefficients) have been deposited at
the Cambridge Crystallographic Data Centre, 12 Union
Road, Cambridge CB2 1EZ, UK. Experimental data: mp:
4. Seki, M.; Simizu, T.; Inubushi, K. Synthesis 2002, 361–364.
5. Martin, A.; Reyes, B.; Pedro, C.; Jimenez, J. L.; Juan, P. C.;
Concepcion, V. Tetrahedron 1993, 49, 2676–2690, and
references cited therein.
6. Crystal data of compound 3: C14H18N2O5 M = 294.3;
˚
space group Monoclinic, P2(1), a = 7.6332(12)A, b =
25
57–59ꢁC; ½aD þ18:69 (c 0.58, CHCl3). dH (CDCl3,
200MHz): 2.12 (s, 3H), 3.83 (dd, J = 5.48, 2.74Hz, 1H),
3.89 (d, J = 5.5Hz, 1H), 4.00 (d, J = 2.7Hz, 1H), 4.04 (d,
J = 14.8Hz, 1H), 4.08 (d, J = 15.3Hz, 1H), 4.27
(d, J = 17.7Hz, 1H), 4.39 (d, J = 11.7Hz, 1H), 4.52
(d, J = 17.2Hz, 1H), 4.56 (d, J = 11.7Hz, 1H), 4.92 (d,
J = 15.3Hz, 1H), 4.97(d, J = 14.9Hz, 1H), 7.09–7.46 (m,
15H). dC (CDCl3, 50MHz): 20.1, 46.0, 46.7, 47.0, 57.0, 67.0,
73.7, 79.4, 115.0, 126.2–129.1, 134.9, 135.4, 135.6, 158.1,
169.9, 201.5. MS (ESI) m/z: 511.5 Anal. Calcd for
C30H29N3O5: C 70.43, H 5.71, N 8.21. Found: C 70.70, H
5.59, N 8.17.
˚
˚
9.5764(15)A, c = 9.5875(15)A, b = 100.092(2)ꢁ, a = 90ꢁ
c = 90ꢁ, V = 689.99(19)A3, Dc = 2, 1.417mg/m3 (Mo-
˚
Ka) = 0.108mmꢀ1
,
T = 312; crystal size =0.52 · 0.47 ·
0.16mm; theta range for data collection = 2.16–26.99ꢁ,
limiting indices = 9 6 h 6 9, ꢀ12 6 k 6 12, ꢀ12 6 l 6 12;
reflections collected/unique 7590/2993 [R(int) = 0.0209];
completeness to theta = 26.99, 99.8%, absorption correc-
tion = semi-empirical from equivalents; max. and min.
transmission = 0.9829 and 0.9458, refinement method =
full-matrix least-squares on F2; data/restraints/parameters
8. Luo, F. T.; Jeevanandam, A. Tetrahedron Lett. 1998, 39,
9455–9456.