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Synthetic Studies on (+)-Biotin, Part 11: Application of
Cinchona Alkaloid - Mediated Asymmetric Alcoholysis of
meso-Cyclic Anhydride in the Total Synthesis of (+)-Biotin
Hui-Fang Dai,[a] Wen-Xue Chen,[a] Lei Zhao ,[b] Fei Xiong,[b] Hao Sheng,[b
] and Fen-Er Chen*[a,b] a Fudan- DSM Joint Laboratory for Synthetic Method and Chiral Technology, Fudan University, Shanghai,
200433, P. R. China. b Institute of Biomedical Science, Fudan University, Shanghai, 200031, P. R. China.
Fax: +86(21)65643811. E-mail: [email protected]
1H NMR (400 MHz, CDCl3): (4S, 5R)-1, 3-dibenzyl-2-oxo-5-
((3-phenylallyloxy) carbonyl)imidazolidine-4-carboxylic acid(4)
13C NMR (100 MHz, CDCl3): (4S, 5R)-1, 3-dibenzyl-2-oxo-5-((3-phenylallyloxy) carbonyl)imidazolidine-4-carboxylic acid(4)
IR: (4S, 5R)-1, 3-dibenzyl-2-oxo-5-((3-phenylallyloxy) carbonyl)
imidazolidine-4-carboxylic acid(4)
Chiral HPLC of enantiomeric excess of (4S, 5R)-1, 3-Dibenzyl-2-oxo-5- ((3-phenylallyloxy) carbonyl)imidazolidine-4-carboxylic acid(4)
1H NMR (400 MHz, CDCl3): (3aS, 6aR)-1, 3-dibenzyl-tetrahydro-1H-furo[3,4-d]imida
zole-2, 4-dione(6)
13C NMR (100 MHz, CDCl3): (3aS, 6aR)-1, 3-dibenzyl-tetrahydro-1H-furo-
[3,4-d]imida zole-2, 4-dione(6)
1H NMR (400 MHz, CDCl3): (3aS, 6aR)-1, 3-dibenzyl-tetrahydro-1H-thieno-
[3,4-d]-imidazole-2,4-dione(7)
13C NMR (100 MHz, CDCl3): (3aS, 6aR)-1, 3-dibenzyl-tetrahydro-1H-thieno-
[3,4-d]-imidazole-2,4-dione(7)
1H NMR (400 MHz, CDCl3): Ethyl 5-((3aS, 6aR)-1, 3-dibenzyl-4-hydroxy-
2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoate(8)
IR: Ethyl 5-((3aS, 6aR)-1, 3-dibenzyl-4-hydroxy-2-oxo-hexahydro-
1H-thieno[3,4-d]imidazol-4-yl)pentanoate(8)
1316:04:10
30-Apr-2008FDU Quattro Micro QAA1228080430-DHF-468-02
m/z150 175 200 225 250 275 300 325 350 375 400 425 450 475 500 525 550 575 600 625 650 675 700 725 750 775 800
%
0
100
080430-DHF-468-03 136 (3.638) 1: Scan ES+ 7.53e5323.1
293.3
158.3
167.1
245.3171.5
182.2
215.2
187.2225.1
292.9
267.2
315.4
469.4323.7
345.4344.9
324.4
387.2
365.8437.0410.0
468.9
493.1
493.9555.7
515.2545.3
671.6641.0574.7
625.1596.4
709.6681.3
764.1744.9 771.6 797.2
MS(ESI): Ethyl 5-((3aS, 6aR)-1, 3-dibenzyl-4-hydroxy-2-oxo-hexahydro-
1H-thieno[3,4-d]imidazol-4-yl)pentanoate(8)
1H NMR (400 MHz, CDCl3): Ethyl 5-((3aS, 4S, 6aR)-1, 3-dibenzyl-2-
oxo-hexahydro-1H –thieno[3, 4-d]imidazol-4-yl)pentanoic (9)
13C NMR (100 MHz, CDCl3): Ethyl 5-((3aS, 4S, 6aR)-1, 3-dibenzyl-2-oxo-
hexahydro-1H –thieno[3, 4-d]imidazol-4-yl)pentanoic (9)
2D NOESY : Ethyl 5-((3aS, 4S, 6aR)-1, 3-dibenzyl-2-oxo-hexahydro-1H –thieno
[3, 4-d]imidazol-4-yl)pentanoic (9)
IR: Ethyl 5-((3aS, 4S, 6aR)-1, 3-dibenzyl-2-oxo-hexahydro-1H –thieno[3, 4-d]
imidazol-4-yl)pentanoic (9)
1018:29:30
09-Jan-2008FDU Quattro Micro QAA1228080109-DHF-450
m/z160 180 200 220 240 260 280 300 320 340 360 380 400 420 440 460 480 500 520 540 560 580 600
%
0
100
080109-DHF-450 152 (3.060) Cm (150:164) 1: Scan ES+ 3.46e7453.3
289.2
261.2172.2
157.1
233.2
182.2 205.1
184.3
186.3 218.1 246.2 274.2
407.3311.2
290.4 361.3315.2 352.2379.3 397.1
425.4
408.6 451.3
454.7
455.6475.3
519.3476.6 507.2 537.3 566.5559.1 599.0588.8
MS(ESI): Ethyl 5-((3aS, 4S, 6aR)-1, 3-dibenzyl-2-oxo-hexahydro-1H –thieno
[3, 4-d]imidazol-4-yl)pentanoic (9)