New and efficient approaches to the semisynthesis of taxol and its C-13 side chain analogs by means of ??-lactam synthon method, Tetrahedron, vol.48, issue.34, pp.6985-7012, 1992. ,
DOI : 10.1016/S0040-4020(01)91210-4
A highly efficient synthesis of the C-13 side-chain of taxol using Shibasaki's asymmetric Henry reaction, Tetrahedron Letters, vol.45, issue.18, pp.3689-3691, 2004. ,
DOI : 10.1016/j.tetlet.2004.02.150
)-8-Phenylmenthyl Glyoxylate, The Journal of Organic Chemistry, vol.69, issue.8, pp.2844-2850, 2004. ,
DOI : 10.1021/jo0358269
Highly Stereocontrolled and Efficient Preparation of the Protected, Esterification-Ready Docetaxel (Taxotere) Side Chain, The Journal of Organic Chemistry, vol.59, issue.6, pp.1238-1240, 1994. ,
DOI : 10.1021/jo00085a004
Direct, highly efficient synthesis from (S)-(+)-phenylglycine of the taxol and taxotere side chains, The Journal of Organic Chemistry, vol.56, issue.24, pp.6939-6942, 1991. ,
DOI : 10.1021/jo00024a044
NH 3 ) : calculée pour C 40 H 64 O 5 NSi 2 : 694, pp.694-4340 ,
40 (s l, 1H, H 7 ), 3.62 (s l, 1H, pp.0-4 ,
Diastéréoisomère 235b : R f : 0 ,
CDCl 3 ) : ? = 5, NMR (300 MHz, p.35 ,
60 (s l, 1H, pp.4-386902 ,
µL) was added slowly to a stirred solution of 17 (306 mg, 0.59 mmol) in acetone (3.4 mL) at 0 °C. The mixture was stirred at 0 °C for 4 h and poured onto ice/water. The aqueous layer was extracted with AcOEt and the combined organic layers were washed with brine, dried over MgSO 4 , concentrated in vacuo. Purification of the residue by flash chromatography (cyclohexane/diisopropylether: 8/2) afforded 18 (255 mg, 81%) as a colorless oil, lit.: [3] CHCl 3 ). 1 H NMR (CDCl, pp.614-637 ,
12 (s, 9H), 0.88 (t, 3H, J= 6.7 Hz) 13 C NMR (CDCl 3 , 75 MHz): ?= 175.1, 135, Hz), 4.55 (d, 1H, J= 6.4 Hz), 1.91 (q like, 2H, J= 6.4 Hz), 1.26 (br s, 24H) Hz), 3.44 (dd, 1H, J= 11.3 and 9.9 Hz), 3.43- 3.33 (m, 1H) 6.7 Hz). 13 C NMR (CDCl, pp.60-67 ,
R,3'E)-2-N-(2'-tert-butyldiphenylsilyloxy- 3'-octadecenoyl)-1,3-O-isopropyliden-[2-amino- octadecan-1,3-diol] (21) To a solution of 20 (31 mg, 0.09 mmol) and 18 (59 mg, 0.11 mmol) in CH 2 Cl 2 (1.5 mL) were added HATU (41 mg, 0.11 mmol) and diisopropylamine (47 µL, 0.27 mmol) at 0 °C. The mixture was stirred for 2 h at 0 °C and filtered on a silica pad, 2S,3R The filtrate was concentrated in vacuo and the residue was purified by flash chromatography (cyclohexane/diisopropylether: 8/2) to afford 21 (50 mg, 64%) as a colorless oil. 1 H NMR (CDCl 3 , 300 MHz): ?= 7, pp.65-72 ,
1.95 (q like, 2H, J= 6.2 Hz), 1.58-1.40 (m, 2H), 1.39 (s, 3H), 1.38 (s, 3H) 13 C NMR (CDCl 3 , 75 MHz): ?= 171, m, 1H), 3.26 (dd, 1H, J= 13.0 and 9.9 Hz) 50H), 1.14 (s, 9H), 0.88 (t, 6H, J= 6.7 Hz, pp.66-71 ,
-tert-butyldiphenylsilyloxy- 3'-octadecenoyl)-1,3-O-isopropyliden-[2-amino- octadecan-1,3-diol] (22) Obtained from (ent)-20 (32 mg, 0.09 mmol) and 18 (60 mg, 0.11 mmol) following the procedure described for compound 21. Purification of the residue by flash chromatography (cyclohexane/diisopropylether, 74%) as a colorless oil. 1 H NMR (CDCl 3 , 300 MHz): ?= 7, p.61 ,
URL : https://hal.archives-ouvertes.fr/in2p3-00654867
12 (m, 2H), 1.58-1.36 (m, 4H), 1.42 (s, 3H), 1.38 (s, 3H), 1.25 (br s, 48H), 0, 2H), 2.98 (br s, 1H) 6.7 Hz). 13 C NMR (CDCl 3 , 75 MHz): ?= 172, pp.4-8397 ,
13 C NMR (CDCl 3 , 100 MHz, 50°C): ?= 173 ,
43 (s, 3H), 1.39 (s, 3H), 1.24 (br s, 26H), 0, 3H, J= 6.7 Hz). 13 C NMR (CDCl 3 , 75 MHz): ?= 98, pp.4755-4756 ,
-tert- butyldiphenylsilyloxy-3'-octadecenoyl)-1,3-O- isopropyliden-[2-amino-octadecan-1,3-diol] (34) Obtained from 33 (37 mg, 0.11 mmol) and 18 (70 mg, 0.13 mmol) following the procedure described for compound 21. Purification of the residue by flash chromatography (cyclohexane/diisopropylether: 8/2) afforded 34 (70 mg, 75%) as a colorless oil, H NMR (CDCl 3 , 300 MHz): ?= 7.69 (d, 1H, J= 12.9 Hz), p.66 ,
URL : https://hal.archives-ouvertes.fr/in2p3-00654867
7 Hz) 13 C NMR (CDCl 3 , 75 MHz): ?= 171 (2R,3R,2'R,3'E)-2-N-(2'-tert- butyldiphenylsilyloxy-3'-octadecenoyl)-[2-amino- octadecan-1,3-diol] (36) Obtained from 34 (67 mg, 0.078 mmol) following the procedure described for compound 23. Purification of the residue by flash chromatography (cyclohexane/AcOEt: 8/2) afforded 36 (40 mg, 63%) as a white solid, .4 and 6.3 Hz), 4.61 (d, 1H, J= 6.2 Hz), 3.91 (br s, 1H), 3.87-3.74 (m, 3H), 2.73 (br s, 1H), pp.99-102 ,
-hydroxy-3'- octadecenoyl)-[2-amino-octadecan-1,3-diol] (38) Obtained from 36 (38 mg, 0.046 mmol) following the procedure described for compound 1. Purification of the residue by flash chromatography (cyclohexane/AcOEt: 6/4) afforded 38 (19 mg, 70%) as a white solid, CHCl 3 ). 1 H NMR (CDCl 3 , 400 MHz, pp.50-56 ,
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94 (br s, 1H), 2.35 (br s, 1H), 2.28 (br s, 1H), 1H), 3.84 (d like, 2H, J= 4.2 Hz) 2H, J= 6.9 Hz), 1.53-1.37 (m, 6H), 1.29 (br s, pp.5999-6002 ,
Catalytic Asymmetric Synthesis, pp.343-436, 2010. ,
URL : https://hal.archives-ouvertes.fr/hal-00351129
13, 578; i) H. Pellissier, Chem. Biol. Chem. Soc. Rev. Curr. Opin. Biotechnol. Tetrahedron Angew. Chem. Int. Ed, vol.321, issue.44, p.3974, 2000. ,
64, 1563; n) H. Pelissier, Adv. Synth. Catal. 2011, 353, 659. [11] For the anti-selective ruthenium-mediated asymmetric hydrogenation of ?-amino-?-ketoester derivatives by DKR, see: a) K, Tetrahedron, 2008. ,
One-Pot Multistep Bohlmann???Rahtz Heteroannulation Reactions:?? Synthesis of Dimethyl Sulfomycinamate, The Journal of Organic Chemistry, vol.70, issue.4, p.1389, 2005. ,
DOI : 10.1021/jo048106q
Syntheses of all of the racemic diastereoisomers of phytosphingosine, The Journal of Organic Chemistry, vol.35, issue.2, p.350, 1970. ,
DOI : 10.1021/jo00827a013
The Catalyst Precursor, Catalyst, and Intermediate in the RuII-Promoted Asymmetric Hydrogen Transfer between Alcohols and Ketones, Angewandte Chemie International Edition in English, vol.36, issue.3, p.285, 1997. ,
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Highly enantioselective borane reduction of ketones catalyzed by chiral oxazaborolidines. Mechanism and synthetic implications, Journal of the American Chemical Society, vol.109, issue.18, pp.5551-7925, 1977. ,
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Novel, general synthesis of the chiral catalysts diphosphine-ruthenium (II) diallyl complexes and a new practical in situ preparation of chiral ruthenium (II) catalysts, Tetrahedron: Asymmetry, vol.5, issue.4, p.665, 1994. ,
DOI : 10.1016/0957-4166(94)80029-4
13 C NMR (CDCl 3 , 50 MHz, 24 °C): d 165.2, 133, Anti diastereisomer 1 H NMR (CDCl 3 , 300 MHz, 24 °C): d 8.07 (m, 2H), pp.58-65 ,
Hz, 3H) 13 C NMR (CDCl 3 , 50 MHz, 24 °C): d 165, 8 Hz), 18.1 (d, J = 8.5 Hz)9 Hz). HPLC: Chiralcel AS-H, 991S,2R), 72.6 min for (1R,2S), 127.7 min and 144.1 min for (1R,2S) and (1S,2R), pp.4-2758 ,
64 (s, 1H), 3.83 (s, 3H) 13 C NMR (CDCl 3 , 50 MHz, 24 °C): d 188, NMR, vol.3, issue.5 3, pp.24-31, 1269. ,
1.42 (s, 9H) 13 C NMR (CDCl 3 , 75 MHz, 24 °C): d 172, pp.71-313 ,
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then allowed to return to room temperature. Methanol (30 mL) and 3 M NaOH (10 mL) were successively added and the solution was stirred for 12 h at room temperature After the addition of H 2 O (50 mL) and extraction with EtOAc (2 Â 40 mL), the organic phase was dried (MgSO 4 ) and concentrated to give a syrup which was purified by column chromatography (40% AcOEt in cyclohexane) to afford 4 (2.9 g, 72%) as a white solid Mp 104?105 °C; ½a 24 D ¼ þ21:1 (c 1.0, CH 2 Cl 2 ); IR (KBr): m = 3423 (br), 1740, 1449, 1384, 1351 cm À1 ; 1 H NMR (CDCl 3 , 300 MHz) d 2.05 (br s, 1H), 3.60 (dd, J = 3, A mixture of 3 (3.4 g, 14.2 mmol) and Boc 2 O (10.0 g, 45.8 mmol) was heated at 60?70 °C for 48 h. (1S,2R)-1-(Benzylamino)-3-(tert-butyldimethylsilyloxy)-1- phenylpropan-2-ol 5, pp.20-27, 1986. ,
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Discovery of a potent substance P antagonist: recognition of the key molecular determinant, Journal of Medicinal Chemistry, vol.35, issue.26, p.4911, 1992. ,
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44, 915; For syntheses of (À)-L-733,061, see: (k), Org. Lett. Tetrahedron Lett. Z.-Q J. Org. Chem, vol.5, issue.6, p.3517, 1927. ,
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Asymmetric synthesis of the Abbott amino dihydroxyethylene dipeptide isostere subunit, Tetrahedron Letters, vol.37, issue.26, p.4525, 1996. ,
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