Boc-tryptophanol

Base Information

• Chemical Name: Boc-tryptophanol
• CAS No.: 82689-19-8
• Molecular Formula: C₁₆H₂₂N₂O₃
• Molecular Weight: 290.362
• Hs Code.: 29339900
• DSSTox Substance ID: DTXSID00427137
• Nikkaji Number: J1.170.614B
• Wikidata: Q72450965
• Mol file: 82689-19-8.mol

Synonyms:82689-19-8;BOC-TRYPTOPHANOL;N-BOC-L-Tryptophanol;BOC-L-TRYPTOPHANOL;TERT-BUTYL N-[(2S)-1-HYDROXY-3-(1H-INDOL-3-YL)PROPAN-2-YL]CARBAMATE;(S)-3-(2-(BOC-AMINO)-3-HYDROXYPROPYL)-INDOLE;Boc-Trp-ol;N-tert-Butoxycarbonyl-L-tryptophanol;Nalpha-Boc-L-tryptophanol;BOC-(S)-2-AMINO-3-(3-INDOLYL)-1-PROPANOL;SCHEMBL3560147;DTXSID00427137;(S)-tert-butyl 1-hydroxy-3-(1H-indol-3-yl)propan-2-ylcarbamate;MFCD00235953;tert-butyl (S)-(1-hydroxy-3-(1H-indol-3-yl)propan-2-yl)carbamate;AKOS015898393;AC-8566;CS-W009151;N-alpha-t-Butyloxycarbonyl-L-tryptophanol;Nalpha-(tert-Butoxycarbonyl)-L-tryptophanol;(S)-2-(Boc-amino)-3-(3-indolyl)propanol;B4287;N-I+/--(tert-Butoxycarbonyl)-L-tryptophanol;N- alpha -(tert-Butoxycarbonyl)-L-tryptophanol;8Z-5030;A840415;N-alpha-(tert-Butoxycarbonyl)-L-tryptophanol, 98%;(S)-2-(tert-Butoxycarbonyl)amino-3-(3-indolyl)propanol;(S)-2-(tert-Butoxycarbonylamino)-3-(1H-indole-3-yl)-1-propanol;tert-Butyl [(2S)-1-hydroxy-3-(1H-indol-3-yl)propan-2-yl]carbamate;tert-butyl N-[(2S)-1-(1H-indol-3-yl)-3-oxidanyl-propan-2-yl]carbamate;N-[(2S)-1-hydroxy-3-(1H-indol-3-yl)propan-2-yl]carbamic acid tert-butyl ester

Chemical Property of Boc-tryptophanol

Chemical Property:

• Appearance/Colour: White to off-white powder
• Vapor Pressure: 1.47E-11mmHg at 25°C
• Melting Point: 118-122 °C(lit.)
• Refractive Index: 1.593
• Boiling Point: 518.1 °C at 760 mmHg
• PKA: 12.06±0.46(Predicted)
• Flash Point: 267.1 °C
• PSA: 74.35000
• Density: 1.19 g/cm³
• LogP: 2.98690
• Storage Temp.: Store at 0°C
• Solubility.: soluble in Methanol
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 290.16304257
• Heavy Atom Count: 21
• Complexity: 354

Purity/Quality:

98%,99%, ^*data from raw suppliers

Nα-(tert-Butoxycarbonyl)-L-tryptophanol >98.0%(HPLC)(N) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CNC2=CC=CC=C21)CO
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CNC2=CC=CC=C21)CO

Technology Process of Boc-tryptophanol

There total 12 articles about Boc-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%

Boc-Trp-OH (13139-14-5) → N-t-butoxycarbonyl-tryptophanol (110659-38-6,143259-51-2,82689-19-8)

Guidance literature:

Boc-Trp-OH; With 4-methyl-morpholine; isobutyl chloroformate; In tetrahydrofuran; at -15 ℃; for 0.25h;

With sodium tetrahydroborate; In tetrahydrofuran; water; at -15 ℃; for 1h;

DOI:10.1128/AAC.01152-16

Reference yield: 100.0%

3-(1-benzyl-1H-indol-3-yl)-2-tert-butoxycarbonylamino-propionic acid methyl ester (219497-33-3) → N-t-butoxycarbonyl-tryptophanol (110659-38-6,143259-51-2,82689-19-8)

Guidance literature:

With ammonia; sodium; at -40 ℃; for 0.0166667h;

DOI:10.1039/c5ob01438g

Reference yield: 95.0%

methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoate (141215-69-2,33900-28-6) → N-t-butoxycarbonyl-tryptophanol (110659-38-6,143259-51-2,82689-19-8)

Guidance literature:

methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoate; With sodium tetrahydroborate; In ethanol; at 0 - 30 ℃; for 10h;

With ammonium chloride; In ethanol; at 0 - 5 ℃;

upstream raw materials:

Boc-Trp-OH

C₂₁H₂₈N₂O₆

methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoate

di-tert-butyl dicarbonate

Downstream raw materials:

[1-(3-bromo-phenoxymethyl)-2-(1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester

2S-N₂-[[2-(t-Butoxycarbonyl)amino-3-(1H-indol-3-yl)]propoxycarbonyl]-N₄-(2,2-dimethyl-3-oxo-4H-5-pyrido[1,4]oxazin-6-yl)-5-fluoro-N₂-(3,4,5-trimethoxyphenyl)-2,4-pyrimidinediamine

C₂₆H₃₁N₃O₆

C₂₁H₂₃N₃O₄*ClH

Refernces

• 1、 Maity, Arindam,Munda, Mintu,Niyogi, Sovan,Kumar, Nivesh,Bisai, Alakesh. "Total syntheses of Hexahydropyrrolo[2,3-b]indole Alkaloids, (+)-pseudophrynamine 270 and (+)-pseudophrynamine 272A". . . Retrieved 2021/12/09.
• 2、 Kondaparla, Srinivasarao,Debnath, Utsab,Dola, Vasantha Rao,Sinha, Manish,Katti, Seturam B.,Soni, Awakash,Srivastava, Kumkum,Puri, Sunil K.. "Synthesis, biological evaluation, and molecular modeling studies of chiral chloroquine analogues as antimalarial agents". . . Retrieved 2019/01/05.