D-7-Azatryptophan

Base Information

• Chemical Name: D-7-Azatryptophan
• CAS No.: 134235-82-8
• Molecular Formula: C10H11N3O2
• Molecular Weight: 205.216
• UNII: W6B510DC3B
• DSSTox Substance ID: DTXSID40428421
• Nikkaji Number: J727.807A
• Mol file: 134235-82-8.mol

Synonyms:D-7-Azatryptophan;134235-82-8;7-Aza-D-tryptophan;1H-Pyrrolo[2,3-b]pyridine-3-propanoic acid, a-amino-, (aR)-;(R)-2-Amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoic acid;(2R)-2-amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoic acid;W6B510DC3B;1H-Pyrrolo[2,3-b]pyridine-3-propanoic acid,a-amino-,(aR)-;(R)-2-Amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-propionic acid;(2R)-2-AMINO-3-{1H-PYRROLO[2,3-B]PYRIDIN-3-YL}PROPANOIC ACID;(-)-(r)-7-azatryptophan;UNII-W6B510DC3B;SCHEMBL12223910;(aR)-a-Amino-1H-pyrrolo[2,3-b]pyridine-3-propanoic acid;DTXSID40428421;MFCD10565743;AS-70811;CS-0004118;CS-0012684;J-006505;(R)-2-Amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoicacid;(alphaR)-alpha-Amino-1H-pyrrolo[2,3-b]pyridine-3-propanoic acid;1H-Pyrrolo(2,3-b)pyridine-3-propanoic acid, alpha-amino-, (alphaR)-;1H-Pyrrolo[2,3-b]pyridine-3-propanoic acid, |A-(acetylamino)-, (|AR)-;1H-PYRROLO(2,3-B)PYRIDINE-3-PROPANOIC ACID, .ALPHA.-AMINO-, (.ALPHA.R)-

Chemical Property of D-7-Azatryptophan

Chemical Property:

• PSA: 92.00000
• LogP: 1.21760
• Storage Temp.: 2-8°C
• XLogP3: -2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 205.085126602
• Heavy Atom Count: 15
• Complexity: 247

Purity/Quality:

99%+, ^*data from raw suppliers

(R)-2-Amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoicacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(NC=C2CC(C(=O)O)N)N=C1
• Isomeric SMILES: C1=CC2=C(NC=C2C[C@H](C(=O)O)N)N=C1

Technology Process of D-7-Azatryptophan

There total 18 articles about D-7-Azatryptophan which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

C19H21N3O2 → (-)-(R)-7-azatryptophan (134235-82-8,1137-00-4) + (S)-2-amino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)propanoic acid (49758-35-2,1137-00-4)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; at 20 ℃; for 8h; under 3040.2 Torr;

DOI:10.1002/bkcs.10287

Reference yield: 69.0%

tert-butyl α-amino-β-(1-tert-butyloxycarbonyl-7-azaindolyl)propionate (144657-73-8) → (-)-(R)-7-azatryptophan (134235-82-8,1137-00-4)

Guidance literature:

With trifluoroacetic acid; at 21 ℃; for 2h;

Reference yield: 40.0%

(R)-2-Acetylamino-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-propionic acid → (-)-(R)-7-azatryptophan (134235-82-8,1137-00-4)

Guidance literature:

With hydrogenchloride; for 4h; Heating;

DOI:10.1016/S0957-4166(98)00130-X

upstream raw materials:

tert-butyl α-amino-β-(1-tert-butyloxycarbonyl-7-azaindolyl)propionate

diethyl 2-((1H-pyrrolo[2,3-b]pyridin-3-yl)methyl)-2-acetamidomalonate

N^α-Acetyl-DL-7-azatryptophan

7-Azaindole

Refernces

• 1、 Gee, Moon Bae,Kim, Tae Seung,Yum, Eul Kgun. "Palladium-catalyzed heteroannulation approach to 7-azatryptophan with a Sch?llkopf chiral auxiliary". . p. 1546 - 1549. Retrieved 2015/07/15.
• 2、 Sanchez-Obregon, Ruben,Fallis, Alex G.,Szabo, Arthur G.. "Syntheses of a potential fluorescence probe, (-)-(R)-7-azatryptophan, via alkylation of the (1R,4R)-camphor imine of tert-butylglycinate". . p. 1531 - 1536. Retrieved 2007/10/02.