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Chemical Structure| 13292-22-3 Chemical Structure| 13292-22-3
Chemical Structure| 13292-22-3

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3-Formyl rifamycin is a rifamycin derivative antibiotic that binds to the β-subunit of RNA polymerase, preventing transcription and inhibiting RNA synthesis, thereby suppressing bacterial growth and proliferation.

Synonyms: Rifaldehyde; NCI 145-635; 3-formyl Rifampicin SV

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Product Details of 3-Formyl rifamycin

CAS No. :13292-22-3
Formula : C38H47NO13
M.W : 725.78
SMILES Code : C[C@@]([C@@](O)([H])[C@@]([C@](O)([H])[C@@]([C@@](OC(C)=O)([H])[C@]([C@](OC)([H])/C([H])=C([H])/O[C@@]1(C(C2=C(O1)C(C)=C(O)C3=C2C(O)=C(C4=C3O)C=O)=O)C)([H])C)([H])C)([H])C)([H])/C([H])=C([H])/C([H])=C(\C(O)=N\4)C
Synonyms :
Rifaldehyde; NCI 145-635; 3-formyl Rifampicin SV
MDL No. :MFCD01729454

Safety of 3-Formyl rifamycin

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 3-Formyl rifamycin

* 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 [ 13292-22-3 ]

[ 13292-22-3 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 3279-95-6 ]
  • [ 13292-22-3 ]
  • [ 38128-93-7 ]
  • 2
  • [ 34800-90-3 ]
  • [ 13292-22-3 ]
  • [ 51707-04-1 ]
  • 3
  • [ 2899-28-7 ]
  • [ 13292-22-3 ]
  • C51H63N3O14 [ No CAS ]
YieldReaction ConditionsOperation in experiment
31% General procedure: 3-Formyl-rifamycin SV (RAL) was purchased from LKT Laboratories Inc. (>98%). RAL (250.0 mg, 0.34 mmol, Fluka) was dissolved in 50 ml CH2Cl2 and after the addition of catalyst (0.025 mmol HCl/EtOH) respective mixtures were prepared with each of the following compounds taken separately: L- Phenylalanine benzyl ester hydrochloride, L- Phenylalanine tert-butyl ester hydrochloride, L-Phenylalanine ethyl ester hydrochloride, L- Phenylalanine methyl ester hydrochloride, L-Tryptophan benzyl ester, L-Tryptophan ethyl ester hydrochloride, L-Tryptophan methyl ester hydrochloride, L-Tyrosine ethyl ester, L-Tyrosine methyl ester hydrochloride, L-Histidine methyl ester dihydrochloride, L-Lysine ethyl ester dihydrochloride and L-Arginine ethyl ester dihydrochloride in 1 ml of CH3OH. Amino acid esters containing hydrochloride were neutralized with an equivalent amount of KOH/EtOH (0.06 M) solution. The mixtures were stirred at 40C for half an hour and after that 3/4 of the solvent volume was distilled off. To the cooled reaction mixture (room temperature) the reductant NaBH3CN (13 mg, 0.15 mmol) was added portionwise over 1 min. The reaction mixture was stirred for one hour. Next the reaction mixture was evaporated to dryness, dissolved in 50 ml of CH2Cl2 and extracted twice with 50 ml of water and brine. The separated organic layer was evaporated and the synthesized derivatives of 3-formylrifamycin SV (compounds 1-12) were next purified by column chromatography with silica gel (25 cm × 1 cm, silica gel 60, 0.040-0.063 mm/230-400 mesh ASTM, Fluka) with dichloromethane/methanol (40:1) as an eluent.
  • 4
  • [ 4089-07-0 ]
  • [ 13292-22-3 ]
  • C49H62N2O15 [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% General procedure: 3-Formyl-rifamycin SV (RAL) was purchased from LKT Laboratories Inc. (>98percent). RAL (250.0 mg, 0.34 mmol, Fluka) was dissolved in 50 ml CH2Cl2 and after the addition of catalyst (0.025 mmol HCl/EtOH) respective mixtures were prepared with each of the following compounds taken separately: L- Phenylalanine benzyl ester hydrochloride, L- Phenylalanine tert-butyl ester hydrochloride, L-Phenylalanine ethyl ester hydrochloride, L- Phenylalanine methyl ester hydrochloride, L-Tryptophan benzyl ester, L-Tryptophan ethyl ester hydrochloride, L-Tryptophan methyl ester hydrochloride, L-Tyrosine ethyl ester, L-Tyrosine methyl ester hydrochloride, L-Histidine methyl ester dihydrochloride, L-Lysine ethyl ester dihydrochloride and L-Arginine ethyl ester dihydrochloride in 1 ml of CH3OH. Amino acid esters containing hydrochloride were neutralized with an equivalent amount of KOH/EtOH (0.06 M) solution. The mixtures were stirred at 40°C for half an hour and after that 3/4 of the solvent volume was distilled off. To the cooled reaction mixture (room temperature) the reductant NaBH3CN (13 mg, 0.15 mmol) was added portionwise over 1 min. The reaction mixture was stirred for one hour. Next the reaction mixture was evaporated to dryness, dissolved in 50 ml of CH2Cl2 and extracted twice with 50 ml of water and brine. The separated organic layer was evaporated and the synthesized derivatives of 3-formylrifamycin SV (compounds 1-12) were next purified by column chromatography with silica gel (25 cm × 1 cm, silica gel 60, 0.040-0.063 mm/230-400 mesh ASTM, Fluka) with dichloromethane/methanol (40:1) as an eluent.
  • 5
  • [ 138377-80-7 ]
  • [ 13292-22-3 ]
  • C43H57N3O13 [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% General procedure: 3-Formyl-rifamycin SV (RAL)was purchased from LKT Laboratories Inc. (>98%). RAL (250.0mg, 0.34 mmol) was dissolved in 50 ml CH2Cl2 and afterthe addition of catalyst (0.025 mmol HCl/EtOH) respective mixtures wereprepared with each of the following compounds taken separately: 1-adamantylamine,1-methylpiperazine,1-(2-pyridyl)piperazine,1-(4-fluorobenzyl)piperazine,1-(2,4,6-trimethylbenzyl)piperazine, 1-bis(4-fluorophenyl)methylpiperazine, 1-(ethanesulfonyl)piperazine, 1-(methylsulfonyl)piperidin-4-amine, 4-(dimethylamino)-piperidine,1-(4-pyridyl)piperazine, 1-(2-pyrimidyl)piperazinedihydrochloride, 1,9-dimethyl-1,4,9-triazaspiro[5.5]undecanetrihydrochloride, 3,4-dihydro-2H-spiro[isoquinoline-1,4?-piperidine],n-piperidin-4-yl-methanesulfonamide,1-[3-(trifluoromethyl)pyrid-2-yl]piperazine,1-(cyclohexylmethyl)-4-piperidinamine,1,4?-bipiperidine-4-carboxylic acid dihydrochloride, (4-amino-1-piperidinyl)acetic acid dihydrochloride, 2-oxo-2-(1-piperidinyl)ethanamine,1-(2-amino-ethyl)-pyrrolidin-2-one,4-amino-1-Boc-piperidine, 3-amino-2-piperidinonehydrochloride, 1-acetyl-4-aminopiperidine hydrochloride in1 ml of CH3OH. Amines containinghydrochloride were neutralized with an equivalent amount of KOH/EtOH (0.06 mmolor 0.12 mmol or 0.18 mmol) solution. The mixtures were stirred at 40C for halfan hour and after that 3/4 of the solvent volume was distilled off. To thecooled reaction mixture (room temperature) the reductant NaBH3CN (13mg, 0.15 mmol) was added portionwise over 1 min. The reaction mixture wasstirred for one hour. Next the reaction mixture was evaporated to dryness,dissolved in 50 ml of CH2Cl2 and extracted twice with 50ml of water and brine (theses stages were omitted for reactions with1,4?-bipiperidine-4-carboxylic acid dihydrochloride,(4-amino-1-piperidinyl)acetic acid dihydrochloride). The separated organiclayer was evaporated and the synthesized derivatives of 3-formylrifamycin SV(compounds 1-23) were next purified by column chromatography with silicagel (25 cm × 1 cm, silica gel 60, 0.040-0.063 mm/230-400 mesh ASTM, Fluka) withdichloromethane/methanol (from 200:1 to 3:1) as an eluent.
 

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• Acyl Group Substitution • Appel Reaction • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bouveault-Blanc Reduction • Bucherer-Bergs Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Catalytic Hydrogenation • Chugaev Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Corey-Kim Oxidation • Dess-Martin Oxidation • Ester Cleavage • Fischer Indole Synthesis • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Heat of Combustion • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Jones Oxidation • Julia-Kocienski Olefination • Knoevenagel Condensation • Lawesson's Reagent • Leuckart-Wallach Reaction • Martin's Sulfurane Dehydrating Reagent • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mitsunobu Reaction • Moffatt Oxidation • Mukaiyama Aldol Reaction • Nomenclature of Ethers • Nozaki-Hiyama-Kishi Reaction • Oxidation of Alcohols by DMSO • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Alcohols • Preparation of Aldehydes and Ketones • Preparation of Amines • Preparation of Ethers • Prins Reaction • Reactions of Alcohols • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Ethers • Reactions with Organometallic Reagents • Reformatsky Reaction • Ritter Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Sharpless Olefin Synthesis • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Stetter Reaction • Stobbe Condensation • Swern Oxidation • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

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