151872-21-8

Basic information

• Product Name: D-Tryptophan, N-[(1,1-dimethylethoxy)carbonyl]-, methyl ester
• CAS NO: 151872-21-8
• Molecular Formula: C17H22N2O4
• Molecular Weight: 318.373
• Mol File: 151872-21-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: D-Tryptophan, N-[(1,1-dimethylethoxy)carbonyl]-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: D-Tryptophan, N-[(1,1-dimethylethoxy)carbonyl]-, methyl ester(151872-21-8)
• EPA Substance Registry System: D-Tryptophan, N-[(1,1-dimethylethoxy)carbonyl]-, methyl ester(151872-21-8)

Safety Data

• Hazardous Substances Data: 151872-21-8(Hazardous Substances Data)

Upstream product

• 615-43-0 2-iodophenylamine 
• 192314-71-9 methyl (S)-2-N,N-di(tert-butoxycarbonyl)amino-5-oxopentanoate 

Downstream Products

• 158932-00-4 (R)-tert-butyl (1-hydroxy-3-(1H-indol-3-yl)propan-2-yl)carbamate 
• 1422538-31-5 (S)-methyl 2-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxo-3-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)pyrrolidin-1-yl)propanoate 
• 1422538-30-4 (2R,4S)-benzyl 2-tert-butyl-5-oxo-4-(2-oxoethyl)-4-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)oxazolidine-3-carboxylate 
• 1422538-29-1 (2R,4R)-benzyl 4-allyl-2-tert-butyl-5-oxo-4-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)oxazolidine-3-carboxylate 
• 1422538-28-0 (2R,4R)-benzyl 2-tert-butyl-5-oxo-4-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)oxazolidine-3-carboxylate 
• 1422538-40-6 C₄₆H₅₇N₇O₇ 
• 1422538-39-3 C₃₇H₄₈N₆O₆ 
• 1422538-35-9 (S)-methyl 2-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxo-3-((1-(triisopropylsilyl)-1H-indol-3-yl)methyl)pyrrolidin-1-yl)-6-((tert-butoxycarbonyl)amino)hexanoate 
• 1352575-51-9 C₃₆H₃₂N₄O₅ 
• 1352575-53-1 (5aS,10bR)-benzyl 10b-(1-((benzyloxy)carbonyl)-1H-indol-3-yl)-2-methyl-1,3,4-trioxo-3,4,5a,10b-tetrahydro-1H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-6(2H)-carboxylate 
• 1352575-54-2 (3aR,8aS)-benzyl 3a-(1-((benzyloxy)carbonyl)-1H-indol-3-yl)-2-(methylcarbamoyl)-3,3a-dihydropyrrolo[2,3-b]indole-8(8aH)-carboxylate 
• 1352575-56-4 (2R,3aR,8aS)-8-benzyl 1-tert-butyl 3a-(1-((benzyloxy)carbonyl)-1H-indol-3-yl)-2-(methylcarbamoyl)-3,3a-dihydropyrrolo[2,3-b]indole-1,8(2H,8aH)-dicarboxylate 
• 1352575-50-8 (2R,3aR,8aS)-8-benzyl 1-tert-butyl 3a-(1H-indol-3-yl)-2-(methylcarbamoyl)-3,3a-dihydropyrrolo[2,3-b]indole-1,8(2H,8aH)-dicarboxylate 
• 1352575-49-5 (2R,3aR,8aS)-8-benzyl 1-tert-butyl 3a-(2-formyl-1H-indol-3-yl)-2-(methylcarbamoyl)-3,3a-dihydropyrrolo[2,3-b]indole-1,8(2H,8aH)-dicarboxylate 

Relevant articles and documents

Palladium-catalyzed, modular synthesis of highly functionalized indoles and tryptophans by direct annulation of substituted o-haloanilines and aldehydes

(Chemical Equation Presented) One-pot synthesis of indoles by a palladium-catalyzed annulation of ortho-haloanilines and aldehydes has been developed. Coupling of ortho-iodoaniline with aldehyde is realized under mild ligandless conditions [Pd(OAc)2, DABCO, DMF, 85°C], whereas X-Phos is found to be the ligand of choice for coupling reactions involving ortho-chloroanilines/ortho-bromoanilines and aldehydes. A variety of orthohaloanilines with different electronic properties are suitable substrates, and aldehydes including chiral ones participated in this reaction without racemization. Coupling of (S)-2-N,N-di-tert-butoxycarbonyl-5-oxopentanoate, derived from L-glutamic acid, with ortho-haloanilines provides a rapid access to the ring-A-substituted tryptophans in good to excellent yields.