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Chemical Structure| 4467-54-3 Chemical Structure| 4467-54-3

Structure of H-D-His-OMe·2HCl
CAS No.: 4467-54-3

Chemical Structure| 4467-54-3

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Product Details of [ 4467-54-3 ]

CAS No. :4467-54-3
Formula : C7H13Cl2N3O2
M.W : 242.10
SMILES Code : O=C(OC)[C@H](N)CC1=CNC=N1.[H]Cl.[H]Cl
MDL No. :MFCD00066137
InChI Key :DWAYENIPKPKKMV-QYCVXMPOSA-N
Pubchem ID :12658398

Safety of [ 4467-54-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313

Application In Synthesis of [ 4467-54-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 4467-54-3 ]

[ 4467-54-3 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 1738-87-0 ]
  • [ 4467-54-3 ]
  • [ 2592-22-5 ]
  • 2
  • [ 131543-46-9 ]
  • [ 4089-07-0 ]
  • [ 4467-54-3 ]
  • [ 219627-53-9 ]
  • ethyl (2S)-3-(4-hydroxyphenyl)-2-[(3S)-3-(imidazole-4-yl)-methyl]-2-oxo-piperazine-1-yl}propionate [ No CAS ]
  • 3
  • [ 1397-89-3 ]
  • [ 4467-54-3 ]
  • amphotericin B N-(L)-methoxyhistidinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With diphenyl phosphoryl azide; triethylamine; In N,N-dimethyl acetamide; for 72h;Inert atmosphere; Example 10 Synthesis of Amide 10 (derivative A21): N-(L)-Histidinamide of AmB In another preferred embodiment the present invention provides the analogue of AmB denominated amide 10 or derivative A21: N-(L)-Histidinamide of AmB, represented by formula X, and prepared according to reaction scheme 7 based on the quantity of reagents showed in table 1b. For this synthesis reaction the compounds required for each equivalent of Amphotericin B are: 10.0 equivalents of (Et)3N, 10.0 equivalents of diphenylphosphorylazide, and 10.0 equivalents of the amine to be used, depending on the amide desired. In a 3-necked flask of 100 mL 0.250 g of AmB were dissolved in 5.0 mL N,N-DMAc; the inert atmosphere was procured by injecting nitrogen to the reaction flask; 0.38 mL of (Et)3N (triethylamine), 0.652 g of dihydrochloride of methyl ester (L)-histidine, and 0.58 mL of diphenylphosphorylazide were added. The progress of the reaction was monitored by thin layer chromatography on silica gel in a chloroform:methanol:water (20:10:1) system. After 72 hours of reaction the reaction product is precipitated with 50 mL of ethyl ether and refrigerated for 12 hours; the ether was decanted, and the resulting product was dissolved in the least amount of 1-butanol. Then the product was washed twice with 100 mL of water. The butanol-water azeotrope was distilled then under reduced pressure (10 mmHg) at 50 C. controlled by oil bath and gentle shaking. After distillation the product was precipitated again with 50 mL of ethyl ether and left in the refrigerator for 12 hours, and the ether was decanted. The product was washed three times with 50 mL of ether, one with 50 mL hexane, and vacuum dried.
  • 4
  • [ 1397-89-3 ]
  • [ 4467-54-3 ]
  • amphotericin B [ No CAS ]
YieldReaction ConditionsOperation in experiment
Et3N was added drop wise to a solution ofAmphotericin B (0.195mMol) and L-Histidinemethyl ester dihydrochloride 21 (0.409mMol, 2.1 eq.) in DMSO until pH = 8. The resultingmixture was stirred for 15 minutes. Afterthis, PyBOP (0.292mMol, 1.5 eq.) was added under nitrogen atmosphere, the flask was sealedand stirred for 72 h at rt. (TLC system: methanol-chloroform-water 20:10:1 v/v). The productwas precipitated and washed with anhydrous diethyl ether (5 x 5 ml) and anhydrous acetone(5 x 30 ml). The suspension obtained was centrifuged at 3500 rpm for 10 minutes. Thesolvent was decanted and the product dried at reduced pressure to obtain a yellowish powdercorresponding to the AmB analogue A21. This compound was obtained in yield 84.9% and isolated as a yellow solid with mp 140-145 C (dec); 1H NMR (Fig 3) (700 MHz, pyridine) delta8.16 (d, J = 12.1 Hz, 1 H, Im-2-H), 7.09 (s, 1 H, Im-5-H), 6.96-6.26 (m, 14 H, olefinicH), 5.89(d, J = 6.8 Hz, 3 H), 5.54 (dd, J = 24.2, 13.8 Hz, 3 H), 5.39-5.20 (m, 4 H), 5.20-4.65 (m, 9 H),4.49 (s, 1 H), 4.40-4.09 (m, 4H), 4.03-3.96 (m, 1H), 3.81-3.36 (m, 6H, methyl ester of L-HisH included), 3.11-2.60 (m, 6H), 2.59-2.39 (m, 3H), 2.30-1.18 (m, 26H, aliphatic H), 1.17-0.95 (m, 2H), 0.93-0.77 (m, 1H). 13C NMR (Fig 4) (176 MHz, pyridine) delta 174.21, 173.85,173.02, 172.21, 150.81, 150.57, 149.91, 137.66, 136.30, 136.20, 136.16, 135.60, 134.98, 134.26,133.54, 133.26, 133.00, 124.18, 124.13, 123.57, 101.69, 98.57, 98.44, 78.84, 76.95, 75.41, 75.33,74.98, 72.32, 70.40, 70.16, 68.68, 67.06, 66.53, 58.32, 54.56, 52.55, 47.74, 46.26, 45.62, 44.08,43.33, 43.24, 41.42, 36.88, 32.28, 30.54, 19.38, 18.95, 18.84, 17.67, 17.64, 13.12, 9.28; HRMS(FAB+): m/z [M + H]+ for C54H82N4O18 calcd: 1075.5702, found: 1075.5719; IR vmax3274.23
 

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