63229-68-5

Basic information

• Product Name: L-Tryptophan, N-(phenylmethyl)-, methyl ester
• CAS NO: 63229-68-5
• Molecular Formula: C19H20N2O2
• Molecular Weight: 308.38
• Mol File: 63229-68-5.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: L-Tryptophan, N-(phenylmethyl)-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Tryptophan, N-(phenylmethyl)-, methyl ester(63229-68-5)
• EPA Substance Registry System: L-Tryptophan, N-(phenylmethyl)-, methyl ester(63229-68-5)

Safety Data

• Hazardous Substances Data: 63229-68-5(Hazardous Substances Data)

Upstream product

• 19779-75-0 N_b-benzylidene-L-tryptophan methyl ester 
• 100-52-7 benzaldehyde 
• 4299-70-1 L-tryptophan methyl ester 
• 153-94-6 D-tryptophan 
• 4299-70-1 D-Tryptophan methyl ester 
• 14907-27-8 (R)-(+)-tryptophan methyl ester hydrochloride 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 177217-34-4 2-(benzylidene-amino)-3-(1H-indol-3-yl)-propionic acid methyl ester 

Downstream Products

• 95689-16-0 (1R,3S)-2-Benzyl-1-((1R,3R,4S,8S)-3-methoxy-5,7-dimethylene-2,6-dioxa-bicyclo[2.2.2]oct-8-ylmethyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester 
• 14464-20-1 2-(benzylamino)-3-(1H-indol-3-yl)propanoic acid 
• 138119-45-6 N-phenylmethyl-N-methyl-L-tryptophan methyl ester 
• 32164-04-8 (S)-(+)-N_b-methyltryptophan methyl ester 
• 219557-56-9 2-<(methoxycarbonyl)methyl>-3-<2-(S)-(methoxycarbonyl)-2-(N^b-benzylamino)ethyl>indole 
• 219557-47-8 (-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-formyl-1H-pyrrolo<2,3-d>carbazole-6-carboxylate 
• 219558-11-9 (-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(1-propenyl)-1H-pyrrolo<2,3-d>carbazole-6-carboxylate 
• 219557-83-2 (-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(dimethoxymethyl)-1H-pyrrolo<2,3-d>carbazole-6-carboxylate 
• 219558-95-9 2-<(methoxycarbonyl)methyl>-3-<2(S)-(methoxycarbonyl)-2-b-(tert-butoxycarbonyl)-N^b-benzylamino>ethyl>indole 
• 219558-45-9 (-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(2-hydroxyacetyl)-1H-pyrrolo<2,3-d>carbazole-6-carboxylate 
• 219557-77-4 (2S,3aS,5R,11bR)-3-Benzyl-2-cyano-5-dimethoxymethyl-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylic acid methyl ester 
• 219558-05-1 (2S,3aS,5S,11bR)-3-Benzyl-2-cyano-5-((E)-propenyl)-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylic acid methyl ester 
• 219557-89-8 (-)-methyl (2S,3aS,5R,11bR)-2-(methoxycarbonyl)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(1-propenyl)-1H-pyrrolo<2,3-d>carbazole-6-carboxylate 
• 697222-83-6 (-)-methyl (2S,3aS,5R,11bR)-2-(methoxycarbonyl)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(dimethoxymethyl)-1H-pyrrolo<2,3-d>carbazole-6-carboxylate 

Relevant articles and documents

Oxazolidinones and 2,5-Dihydrofurans via Zinc-Catalyzed Regioselective Allenylation Reactions of l -α-Amino Aldehydes

The simultaneous control of diastereoselectivity and regioselectivity in Zn-catalyzed allenylation reactions of N-protected l-α-amino aldehydes is reported. A reversal in diastereoselectivity could be realized by variation of the α-amino aldehyde protecti

Biology-oriented combined solid-and solution- phase synthesis of a macroline-like compound collection

Macrolines constitute a class of natural products that has more than 100 members and displays diverse biological activities. These compounds feature a cycloocta[b]indole scaffold that represents an interesting target structure for biology-oriented synthesis (BIOS). We have presented a solid-phase synthesis of isomerically pure cycloocta[b]indoles by employing the Pictet-Spengler reaction and the Dieckmann cyclization as key steps. The scope of this reaction sequence was investigated in more detail by using various additional diversification procedures, such as Pd-catalyzed Sonogashira or Suzuki couplings on a solid phase, thus allowing, for example, the generation of 10-substituted cycloocta-[b]indole derivatives. Finally, solution-phase decoration of the cycloocta[b]indole skeleton by reduction and saponification was evaluated, thereby further extending the scope of the solid-phase synthesis.

General approach for the synthesis of sarpagine indole alkaloids. Enantiospecific total synthesis of (+)-vellosimine, (+)-normacusine B, (-)-alkaloid Q3, (-)-panarine, (+)-Na-methylvellosimine, and (+)-Na-methyl-16-epipericyclivine

The first total synthesis of (+)-Na-methyl-16-epipericyclivine (9) was completed [from D-(+)-tryptophan methyl ester] in an overall yield of 42% (eight reaction vessels). The optical rotation [[α]D +22.8 (c 0.50, CHCl3)] obtained on this material confirmed that the reported optical rotation [[α]D 0 (c 0.50, CHCl 3)]47 was biogenetically unreasonable. The total syntheses of (+)-vellosimine, (+)-normacusine B, (-)-alkaloid Q3, (-)-panarine, and (+)-Na-methylvellosimine are also described. Moreover, a mixed sample (1:1) of synthetic (-)-panarine and natural (-)-panarine yielded only one set of signals in the 13C NMR; this indicated that the two compounds are identical and further confirmed the correct configuration of (+)-vellosimine, (+)-normacusine B, and (-)-alkaloid Q3. In this approach, the key templates, (-)-Na-H,N b-benzyltetracyclic ketone 15a and (-)-Na-methyl,N b-benzyltetracyclic ketone 43 were synthesized on multihundred gram scale by the asymmetric Pictet-Spengler reaction and a stereocontrolled Dieckmann cyclization via improved sequences. An intramolecular palladium (enolate-mediated) coupling reaction was employed to introduce the C(19)-C(20) E-ethylidene function in the sarpagine alkaloids for the first time in stereospecific fashion.