SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 5, 2008, Pages 715-719

Synthesis of aminocyclodextrin carboxylic acids

(3) Hanessian, Stephen a Hocquelet, Céline b Jankowski, Christopher K b,c

a UNIVERSITÉ DE MONTRÉAL (Canada)

b DIF (France)

c UNIVERSITÉ DE MONCTON (Canada)

Author keywords

Amination; Azido cyclodextrin carboxylic acids; and cyclodextrin amino acids

Indexed keywords

ALPHA CYCLODEXTRIN DERIVATIVE; AMINOCYCLODEXTRIN CARBOXYLIC ACID DERIVATIVE; BETA CYCLODEXTRIN DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; SYNTHESIS;

EID: 41349108061 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1042803 Document Type: Article

Times cited : (10)

References (41)

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17
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18
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20
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21
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22
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24
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25
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26
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27
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28
- 41349087687
- 6A-O-tert-Buryldimethylsilyl-2 A-G,3A-G,6B,C,E,F,G-nonadecakis-O-benzyl Cyclomaltoheptaose (5) To a solution of compound 2 (200 mg, 70.2 μmol, 1 equiv) dried overnight under vacuum and dissolved in anhyd CH2Cl2 (2 mL) was added Et3N (21 μL, The mixture was cooled to 0°C. TBSOTf (17.7 μL, 1.1 equiv) was added and the reaction was stirred overnight at r.t. The reaction mixture was evaporated, diluted in CH2Cl2, washed with distilled H2O, and dried with MgSO4. After removal of the solvent, the crude product was purified by chromatography on a silica gel column, eluting with cyclohexane-EtOAc (5:1, 4:1 then pure EtOAc) to obtain compound 5 as a white powder (80 mg, 40, Starting material 2 (54.5, was recovered. R f, 0.33 (cyclohexane-EtOAc, 3:1, 1H NMR 500 MHz, CDCl3
- +.

29
- 41349097257
- 6A-Azido-6Adeoxy-6D-O-tert-butyldimethylsilyl-2A-G,3A-G ,6 B,C,E,F,G-nonadecakis-O-benzyl Cyclomaltoheptaose (8) To a solution of compound 5 (322 mg, 108.7 μmol, 1 equiv) in pyridine (3.6 mL, DMAP (39.8 mg, 326.1 μmol, 3 equiv) was added and the reaction mixture was placed at 0°C After addition of MsCl (33.6 μL, 434.7 μmol, 4 equiv, the reaction was stirred 3 h. The mixture was diluted in CH 2Cl2, treated with H2O, the organic phase was dried (MgSO4) and evaporated to dryness. The residue is then dissolved in DMF (3.6 mL, NaN3 (99 mg, 1.52 mmol, 14 equiv) was added and the mixture was heated at 70°C overnight. The mixture was evaporated to dryness, diluted with CH2Cl2 and distilled H2O. The organic phase was dried MgSO4, The crude product was purified by chromato
- +; on DHB matrix found: 2961.44 [M - 26].

30
- 41349121123
- 6A-Azido-6Adeoxy-2A-G,3 A-G,6B,C,E,F,G-nonadecakis-O-benzyl Cyclomaltoheptaose (11) To a solution of compound 8 (228 mg, 76.3 μmol, 1 equiv) in THF (14 mL, TBAF (152 μL, 2 equiv) was added and the mixture was stirred for 5 h at r.t, then diluted in CH2Cl 2 and processed as described above. After removal of the solvent, the crude product was purified by chromatography on a silica gel column, eluting with cyclohexane-EtOAc (6:1 then 4:1) to give compound 11 as a white powder (90, Rf, 0.24 (cyclohexane-EtOAc, 3:1, IR (KBr, 2100 (N3) cm-1. 1N MR (400 MHz, CDCl 3, δ, 7.09-7.37 (m, 95 H, Harom, 5.57 (d, JH1-H2, 2.9 Hz, 1 H, H-1, 5.50 (d, JH1-H2, 2.9 Hz, 1 H, H-1, 5.39 (d, JH1-H2, 2.9 Hz, 1 H, H-1, 5.37 d, JH1-H2
- +.

31
- 41349092250
- 6D-Azido-6D-deoxy-2A-G,3 A-G,6B,C,E,F,G-nonadecakis-O-benzyl Cyclomaltoheptaose-6A-carboxylic Acid (14) To a solution of compound 11 (154 mg, 53 μmol, 1 equiv) in anhyd CH2Cl 2 (6 mL, Dess-Martin periodinane reagent (68 mg, 160.8 μmol, 3 equiv) was added and the reaction mixture was stirred for 5 h at r.t, then diluted with Et2O, and aq NaHCO3 containing Na 2S2O3 was added. This mixture was stirred for 15 min, extracted successively with NaHCO3 and H2O. The organic phases were dried (MgSO4) and evaporated to dryness. To the residue dissolved in THF-BuOH (1.8:4.2 mL, were added successively of 2-methyl-2-butene (1.8 mL, NaH2PO4 (119 mg) in H 2O (1.8 mL) and of NaClO2 107 mg, The reaction was stirred overnight, diluted in EtOAc an
- +.

32
- 41349097457
- +.
- +.

33
- 41349102286
- 6A-O-tert-Buryldimethylsilyl-2 A-G,3A-G,6B,C,E,F,G-nonadecakis-O-methyl Cyclomaltoheptaose (6) To compound 3 (200 mg, 143 μmol, 1 equiv) dissolved in anhyd CH2Cl2 (4 mL) was added Et3N (1.6 mL, To the reaction was added TBSOTf (36 μL, 1.1 equiv) at 0°C. The mixture was stirred overnight at r.t, diluted in CH 2Cl2 and processed as described above. Purification by chromatography on a silica gel column, eluting with CH2Cl 2-MeOH (97:3) gave 97 mg (45, of compound 6. R f, 0.3 (CH2Cl2-MeOH, 96:4, 1H NMR (400 MHz, CDCl3, δ, 5.05-5.21 (m, 12 H, H-1, 5.02 (d, JH1-H2, 3.4 Hz, 2 H, H-1, 3.62-4.05 (m, H-4, H-5, H-6, OCH3, 3.45-3.61 (m, H-3, H-4, H-5, H-6, OCH3, 3.34-3.42 m, OCH3, 3.16
- +.

34
- 41349109709
- 6A-Azido-6Adeoxy-6D-O-tert-butyldimethylsilyl-2A-G,3A-G,6B,C,E,F,G- nonadecakis-O-methyl Cyclomaltoheptaose (9) A solution of compound 6 (75 mg, 49.5 μmol, 1 equiv) in pyridine (1.6 mL) and DMAP (18 mg, 148.5 μmol, 3 equiv) was placed at 0°C and MsCl (15 μL, 198 μmol, 4 equiv) was added. After 3 h of stirring, the mixture was diluted in CH2Cl2, extracted with H2O, and organic phases were dried (MgSO4) and evaporated to dryness. The residue was then dissolved in DMF (3.6 mL, NaN3 (99 mg, 1.52 mmol, 14 equiv) was added, and the mixture was heated at 70°C overnight. The solution was evaporated to dryness, diluted in CH2Cl2 and washed twice with distilled H2O. The organic phases were dried MgSO4, and the crude product was purified by chromatography on a silica
- +.

35
- 41349086361
- 6A-Azido-6A-deoxy-2A-G,3 A-G,6B,C,E,F,G-nonadecakis-O-methyl Cyclomaltoheptaose (12) To a solution of compound 9 (54 mg, 35 μmol, 1 equiv) in THF (6.7 mL, TBAF (70 μL, 2 equiv) was added and the mixture was stirred 5 h at r.t. Then, H2O was added and the organic phase was separated. After removal of the solvent, the crude product was purified by chromatography on a silica gel column, eluting with CH 2Cl2-MeOH (97:3) to give compound 12 (90, R f, 0.27 (CH2Cl2-MeOH, 96:4, IR (KBr, 2100 (N3) cm-1. 1H NMR (400 MHz, CDCl 3, δ, 5.21 (d, JH1-H2, 3.6 Hz, 2 H, H-1, 5.16 (d, JH1-H2, 3.6 Hz, 1 H, H-1, 5.12 (d, J H1-H2, 3.8 Hz, 1 H, H-1, 5.07-5.10 (m, 7 H, 7 x H-1, 5.05 d, JH1-H2, 3.6 Hz, 1 H, H-1
- +.

36
- 41349085546
- 6D-Azido-6D-deoxy-2A-G,3 A-G,6B,C,E,F,G-nonadecakis-O-methyl Cyclomaltoheptaose-6D-carboxylic Acid (15) To a solution of compound 12 (42 mg, 29.5 μmol, 1 equiv) in anhyd CH2Cl 2 (1.5 mL, Dess-Martin periodinane reagent (70 mg, 165 μmol, 5 equiv) was added. The reaction mixture was stirred 5 h at r.t, diluted in Et2O, and NaHCO3 containing Na2S 2O3 was added. The solution was stirred 15 min, then extracted successively with NaHCO3 and H2O. The organic phases were dried over MgSO4 and evaporated to dryness. To a solution of the residue dissolved in THF-BuOH (0.9:2 mL, were added of 2-methyl-2-butene (0.9 mL, NaH2PO4 (60.2 mg) in H 2O (0.9 mL) and NaClO2 53 mg, The solution was stirred overnight, diluted in EtOAc and extracted with
- 3: 1440.50; found: 1440.8 [M].

37
- 41349095401
- 6A-O-tert-Butyldimethylsilyl-2 A-F,3A-F,6B,C,E,F-hexadecakis -O-benzyl Cyclomaltohexaose (4) The same procedure was used as for 5 starting with compound 1 (1.5 g, 621 μmol) to give 600 mg (42, of compound 4 after purification by column chromatography. Rf, 0.40 (cyclohexane-EtOAc, 3:1, 1H NMR (800 MHz, CDCl3, δ, 7.08-7.33 (m, 80 H, Harom, 5.57 (d, JH1-H2, 3.5 Hz, 1 H, H-1, 5.48 (d, J H1-H2, 3.5 Hz, 1 H, H-1, 5.36 (d, 2J CH2, 10.6 Hz, 1 H, CHPh, 5.32 (d, 2J CH2, 10.6 Hz, 1 H, CHPh, 5.23 (d, 2J CH2, 10.6 Hz, 1 H, CHPh, 5.19 (d, 2J CH2, 10.9 Hz, 1 H, CHPh, 5.04 (d, JH1-H2, 3.2 Hz, 1 H, H-1, 4.96 d, 2JCH2, 11.1
- +.

38
- 41349083513
- 6A-Azido-6Adeoxy-6D-O-tert-butyldimethylsilyl- 2A-F,3A-F,6B,C,E,F- hexadecakis-O-benzyl Cyclomaltohexaose (7) The same procedure was used as for 8 starting with compound 4 (600 mg, 245 μmol) to give 516 mg (85, of compound 7 after purification by column chromatography. Rf, 0.5 (cyclohexane-EtOAc, 3:1, IR (KBr, 2100 (N3) cm1. 1H NMR (800 MHz, CDCl 3, δ, 7.13-7.31 (m, 80 H, Harom, 5.31 (d, JH1-H2, 3.4 Hz, 1 H, H-1, 5.22 (d, 2J CH2, 10.9 Hz, 1 H, CHPh, 5.19 (d, 2J CH2, 10.9 Hz, 1 H, CHPh, 5.18 (d, 2J CH2, 10.9Hz, 1 H, CHPh, 5.15-5.17 (m, 4 H, 3 x CHPh, 1 x H-1, 5.11 (d, 2JCH2, 11.0 Hz, 1 H, CHPh, 5.06 d, JH1-H2, 3
- +.

39
- 41349087467
- 6A-Azido-6Adeoxy-2A-F,3 A-F,6B,C,E,F-hexadecakis-O-benzyl Cyclomaltohexaose (10) Same procedure was used as for 11 starting with compound 7 (496 mg, 194 μmol) to give 420 mg (90, of compound 10 after purification by column chromatography. Rf, 0.3 (cyclohexane-EtOAc, 3:1, IR (KBr, 2100 (N3) cm-1. 1H NMR (800 MHz, CDCl3, δ, 7.09-7.34 (m, 80 H, Harom, 5.54 (d, JH1-H2, 3.7 Hz, 1 H, H-1, 5.51 (d, JH1-H2, 3.7 Hz, 1 H, H-1, 5.47 (d, 2JCH2, 10.5 Hz, 1 H, CHPh, 5.36 (d, 2J CH2, 10.5 Hz, 1 H, CHPh, 5.21 (d, 2J CH2, 10.8 Hz, 1 H, CHPh, 5.15 (d, 2J CH2, 10.8 Hz, 1 H, CHPh, 4.91 (d, 2J CH2, 10.2 Hz, 1 H, CHPh, 4.85-4.90 m, 5 H, 1 x H
- +.

40
- 41349087039
- 6D-Azido-6Ddeoxy-2A-F,3 A-F,6B,C,E,F-hexadecakis-O-benzyl Cyclomaltohexaose-6A-carboxylic Acid (13) The same procedure was used as for 14 starting with compound 10 (380 mg, 156 μmol) to give 325 mg (85, of compound 13 after purification by column chromatography. Rf, 0.2 (pentane-EtOAc, 3:1, IR (KBr, 2100 (N3) cm-1. 1H NMR (800 MHz, CDCl3, δ, 7.06-7.36 (m, 80 H, Harom, 5.71 (d, J H1-H2, 3.7 Hz, 1 H, H-1, 5.69 (d, JH1-H2, 3.1 Hz, 1 H, H-1, 5.51 (d, 2JCH2, 10.2 Hz, 1 H, CHPh, 5.48 (d, 2JCH2, 10.2 Hz, 1 H, CHPh, 5.17 (d, 2JCH2, 10.5 Hz, 1 H, CHPh, 5.09 (d, 2JCH2, 10.9 Hz, 1 H, CHPh, 4.93 d, 2JCH2, 10.2
- +.

41
- 41349083925
- 6D-Amino-6D-deoxy-cyclomaltohexaose-6 A-carboxylic Acid (16) Same procedure was used as for 17 starting with compound 13 (100 mg, 40.75 μmol) to give 36 mg (90, of compound 16. 1H NMR (800 MHz, DMSO, δ, 4.95 (d, 1 H, H-1, 4.84 (d, 1 H, H-1, 4.81 (m, 2 H, H-1, 4.79 (d, 1 H, H-1, 4.69 (d, 1 H, H-1, 3.85 (m, 1 H, H-5, 3.70-3.81 (m, 5 x H-3, 1 x H-4, 3.56-3.68 (1 x H-3, 5 x H-5, 1 x H-6, 3.51-3.53 (1 x H-4, 3.36-3.46 (m, 3 x H-4, 1 x H-6, 3.27-3.34 (m, 6 H, 5 x H-2, 1 x H-6D, 3.19 (m, 2 H, 1 x H-2, 1 x H-4, 3.00 (m, 1 H, H-6D, 13C NMR (200 MHz, DMSO, δ, 100.70-101.87 (C-1, 81.72-84.06 (C-4, 71.40-73.04 (C-3, C-2, C-5, 68.36 (1 x C-5, 59.69-60.62 (5 x C-6, 46.33 1 x C-6, HRMS-ESI, m/z calcd for C36H60O30N: 986.3178 [M, found: 986.3194 [MH
- +.

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