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0342764815
-
-
EDCI = 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; HOAt = 1-hydroxy-7-azabenzotriazole; DCC = 1,3-dicydohexylcarbodiimide; DMAP = 4-dimethylaminopyridine; HOBt = 1-hydoxybenzotriazole; SES = 2-(trimethylsilyl)ethylsulfonyl
-
EDCI = 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; HOAt = 1-hydroxy-7-azabenzotriazole; DCC = 1,3-dicydohexylcarbodiimide; DMAP = 4-dimethylaminopyridine; HOBt = 1-hydoxybenzotriazole; SES = 2-(trimethylsilyl)ethylsulfonyl.
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-
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46
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0342330022
-
-
note
-
Analysis of the starting ester revealed that 23 existed as a mixture (94:6) of enatiomers. The major (S)-enantiomer of 23 was chromatographically purified on a semipreparative Diacel Chiracel OD column (10 μm, 2 × 25 cm. 15% i-PrOH-hexane, 7.0 mL/min flow rate). The relative ratio of enatiomers was determined on an analytical Chiracel OD column (10 μm, 0.46 × 25 cm. 10% i-PrOH-hexane, 1.0 mL/min flow rate). The efluent was monitored at 235 nm, and the enantiomers eluted with a retention time of 9.98 (major S-23) and 11.48 min (minor R-23). respectively (α = 1.15).
-
-
-
-
47
-
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0342764813
-
-
note
-
The epimers of 20 were chromatographically separated, and their relative ratio was determined on a semipreparative Diacel Chiracel OD column (10 μm, 2 × 25 cm, 50% i-PrOH-hexane. 7.0 mL/min flow rate). The effluent was monitored at 265 nm, and the diastereomers eluted with a retention time of 26.3 (20) and 32.3 min (epi-20), respectively (α = 1.23).
-
-
-
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48
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0343199433
-
-
Characterization of these three products may be found in the Supporting Information
-
Characterization of these three products may be found in the Supporting Information.
-
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50
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0000120488
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0343199431
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2O 3/1/1, 23 °C, 10 h (70%)
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2O 3/1/1, 23 °C, 10 h (70%).
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53
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0342330020
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Altering the length of time exposed to the hydrolysis conditions alters the relative amounts of 1-3 obtained
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Altering the length of time exposed to the hydrolysis conditions alters the relative amounts of 1-3 obtained.
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56
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0342764812
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PCT Int. Appl. WO9401408
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Dumaitre, B. A.: Dodic, N.; Daugan, A. C. M.; Pianetti, P. M. C. PCT Int. Appl. WO9401408; Chem. Abstr. 1995, 122, 31342e. A detailed procedure for the preparation of 33 is provided in the Supporting Information.
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Dumaitre, B.A.1
Dodic, N.2
Daugan, A.C.M.3
Pianetti, P.M.C.4
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57
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25944433382
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Dumaitre, B. A.: Dodic, N.; Daugan, A. C. M.; Pianetti, P. M. C. PCT Int. Appl. WO9401408; Chem. Abstr. 1995, 122, 31342e. A detailed procedure for the preparation of 33 is provided in the Supporting Information.
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(1995)
Chem. Abstr.
, vol.122
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59
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0343199427
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Full characterization data are provided in the Supporting Information
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Full characterization data are provided in the Supporting Information.
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