using two programmable dosage pumps. After complete
addition of both solutions, the reaction mixture was stirred
for an additional 48 h at 0 uC and 168 h (7 days) at room
temperature, washed with 50 ml portions of 5 M HCl,
saturated NHCO3, water and brine, and dried (Na2SO4). The
solvent was evaporated off under reduced pressure, and the
crude material purified by column and preparative thin layer
chromatography (silica gel, CH2Cl2–EtOH 5 10 : 0.5–2),
and finally crystallised from EtOH to afford 98 mg (38 %) of
(R,R)-G. Transition temperatures/uC: Cr 125 SmC* 157 N*
191 BP 192 Iso; HRMS m/z: C54H60N2O14S requires 993.3843
[M + 1]+; found: 993.3826; 1H-NMR (500 MHz, CDCl3):
d 5 1.61 (d, J 6.7 Hz, 6H, CH3–CH), 3.62–3.87 (m, 20H,
OCH2), 3.73–3.75 (m, 4H, OCH2), 3.87 (t, J 4.7 Hz, 4H,
OCH2), 4.16 (B of A,A9,B-spin system, J 4.4 Hz, 4H,
270 (12), 215 (8); ESIMS m/z (relative intensity, %): 735 [M +
K]+ (11), 719 [M + Na]+ (58), 697 [M + H]+ (100).
Acknowledgements
This
work
was
supported
by
the
Deutsche
Forschungsgemeinschaft (DFG) and the Fonds der
Chemischen Industrie.
Torsten Hegmann,{a Bernhard Neumann,§a Raik Wolf"b and
Carsten Tschierske*a
aInstitute of Organic Chemistry, Martin-Luther-University
Halle-Wittenberg, Kurt-Mothes-Str. 2, 06120 Halle, Germany.
E-mail: Carsten.tschierske@chemie.uni-halle.de; Fax: +49 345 5527346;
Tel: +49 345 5525664
bInstitute of Pharmaceutical Technology and Biopharmacy,
Martin-Luther-University Halle-Wittenberg,
Wolfgang Langenbeck Str. 4, 06108 Halle, Germany
C(O)OCH2–CH2), 4.33 (A,A9 of A,A9,B-spin system,
J
2.4 Hz, J 4.4 Hz, 4H, C(O)OCH2–CH2), 4.74 (q, J 6.7 Hz,
2H, CH3–CH), 6.83 (d, J 8.7 Hz, 8H, Ar–H), 6.94 (d, J 8.7 Hz,
8H, Ar–H), 7.44 (d, J 8.7 Hz, Ar–H), 7.46 (s, 2H, Ar–H), 7.75
(d, J 8.7 Hz, Ar–H); 13C-NMR (100 MHz, CDCl3): d 5 19.32
(CH3), 65.36, 68.75, 69.92, 70.84, 71.79, 71.90, 72.03, 73.43
(OCH2), 116.15, 116.66 (thda), 124.69 (thda), 127.90 (tph),
128.91 (tph), 130.52 (tph), 134.33 (tph), 139.90 (tph), 159.54
(tph), 160.78 (thda), 168.12 (thda), 172.62 (CLO); EIMS m/z
(relative intensity, %): 992 [M]+ (100), 960 (7), 787 (18),
705 (11), 661 (12), 614 (17), 314 (78), 288 (34), 262 (45),
218 (24), 146 (31), 119 (36), 100 (76); ESIMS m/z
(relative intensity, %): 1031 [M + K]+ (12), 1015 [M + Na]+
(76), 993 [M + H]+ (100).
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