N-alpha-Cbz-L-tryptophanol

Base Information

• Chemical Name: N-alpha-Cbz-L-tryptophanol
• CAS No.: 58889-48-8
• Molecular Formula: C₁₉H₂₀N₂O₃
• Molecular Weight: 324.379
• Mol file: 58889-48-8.mol

Synonyms:Carbamic acid, N-[(1S)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]-, phenylmethyl ester;Carbamic acid, [(1S)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]-, phenylmethyl ester (9CI);Carbamic acid, [2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]-, phenylmethyl ester, (S)-;

Chemical Property of N-alpha-Cbz-L-tryptophanol

Chemical Property:

• PSA: 74.35000
• LogP: 3.38860

Purity/Quality:

98.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-alpha-Cbz-L-tryptophanol

There total 7 articles about N-alpha-Cbz-L-tryptophanol 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: 100.0%

(S)-N-benzyloxycarbonyl-L-tryptophan methyl ester (2717-76-2,130812-44-1,130812-46-3) → benzyl (S)-(1-hydroxy-3-(1H-indol-3-yl)propan-2-yl)carbamate (61535-47-5,58889-48-8)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 - 20 ℃; for 0.5h;

DOI:10.1039/c2cc31735d

Reference yield: 49.0%

benzyl chloroformate (501-53-1,94274-21-2) + L-tryptophanol (154-09-6,526-53-4,2899-29-8,52485-52-6) → benzyl (S)-(1-hydroxy-3-(1H-indol-3-yl)propan-2-yl)carbamate (61535-47-5,58889-48-8)

Guidance literature:

With sodium carbonate; In water; acetone; at 0 - 20 ℃; for 4h;

Reference yield:

Cbz-L-Tryptophan-OSu (50305-28-7) → benzyl (S)-(1-hydroxy-3-(1H-indol-3-yl)propan-2-yl)carbamate (61535-47-5,58889-48-8)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; water; at 0 ℃; for 0.0833333h;

DOI:10.1002/chem.201302732

upstream raw materials:

(S)-N-benzyloxycarbonyl-L-tryptophan methyl ester

benzyl chloroformate

L-tryptophanol

(S)-tryptophan methyl ester hydrochloride

Downstream raw materials:

C₂₄H₂₉N₃O₂

(S)-1-(1-(1H-indol-3-yl)-3-(piperidin-1-yl)propan-2-yl)-3-(3,5-bis(trifluoromethyl)phenyl)thiourea

(S)-2-(((benzyloxy)carbonyl)amino)-3-(1H-indol-3-yl)propyl 4-methylbenzenesulfonate

(2S)-2-[(benzyloxycarbonyl)amino]-3-(1H-indol-3-yl)propyl methanesulfonate

Refernces

• 1、 Jadhav, Sandip V.,Misra, Rajkumar,Singh, Sumeet K.,Gopi, Hosahudya N.. "Efficient access to enantiopure γ4-amino acids with proteinogenic side-chains and structural investigation of γ4- asn and γ4-ser in hybrid peptide helices". . p. 16256 - 16262. Retrieved 2013/12/04.
• 2、 Yeung, Bryan K. S.,Zou, Bin,Rottmann, Matthias,Lakshminarayana, Suresh B.,Ang, Shi Hua,Leong, Seh Yong,Tan, Jocelyn,Wong, Josephine,Keller-Maerki, Sonja,Fischli, Christoph,Goh, Anne,Schmitt, Esther K.,Krastel, Philipp,Francotte, Eric,Kuhen, Kelli,Plouffe, David,Henson, Kerstin,Wagner, Trixie,Winzeler, Elizabeth A.,Petersen, Frank,Brun, Reto,Dartois, Veronique,Diagana, Thierry T.,Keller, Thomas H.. "Spirotetrahydro β-carbolines (spiroindolones): A new class of potent and orally efficacious compounds for the treatment of malaria". experimental part. p. 5155 - 5164. Retrieved 2010/09/05.