82689-19-8

Basic information

• Product Name: N-alpha-Boc-L-tryptophanol
• Synonyms: BOC-TRP-OL;BOC-TRYPTOPHANOL;BOC-(S)-2-AMINO-3-(3-INDOLYL)-1-PROPANOL;BOC-L-TRYPTOPHANOL;BOC-L-TRP-OL;Boc-L-tryptophanol≥ 98% (NMR);N-α-Boc-L-tryptophanol,99%e.e.;BOC-(R)-2-AMINO-3-(3-INDOLYL)-1-PROPANOL
• CAS NO: 82689-19-8
• Molecular Formula: C₁₆H₂₂N₂O₃
• Molecular Weight: 290.36
• Product Categories: Amino Acids;Tryptophan [Trp, W];Amino Alcohols;Boc-Amino acid series;Amino Acid Derivatives;Peptide Synthesis;Tryptophan
• Mol File: 82689-19-8.mol
• Article Data: 25

Chemical Properties

• Melting Point: 118-122 °C(lit.)
• Boiling Point: 518.1 °C at 760 mmHg
• Flash Point: 267.1 °C
• Appearance: White to off-white/Powder
• Density: 1.19 g/cm³
• Vapor Pressure: 1.47E-11mmHg at 25°C
• Refractive Index: 1.593
• Storage Temp.: Store at 0°C
• Solubility: soluble in Methanol
• PKA: 12.06±0.46(Predicted)
• CAS DataBase Reference: N-alpha-Boc-L-tryptophanol(CAS DataBase Reference)
• NIST Chemistry Reference: N-alpha-Boc-L-tryptophanol(82689-19-8)
• EPA Substance Registry System: N-alpha-Boc-L-tryptophanol(82689-19-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 82689-19-8(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

InChI:InChI=1/C16H22N2O3/c1-16(2,3)21-15(20)18-12(10-19)8-11-9-17-14-7-5-4-6-13(11)14/h4-7,9,12,17,19H,8,10H2,1-3H3,(H,18,20)/t12-/m0/s1

Upstream product

• 13139-14-5 Boc-Trp-OH 
• 127476-51-1 C₂₁H₂₈N₂O₆ 
• 141215-69-2 methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 73-22-3 L-Tryptophan 
• 154-09-6 L-tryptophanol 
• 3392-11-8 2,5-dioxopyrrolidin-1-yl N-(tert-butoxycarbonyl)-L-tryptophanate 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 4299-70-1 L-tryptophan methyl ester 
• 219497-33-3 3-(1-benzyl-1H-indol-3-yl)-2-tert-butoxycarbonylamino-propionic acid methyl ester 

Downstream Products

• 82689-14-3 N-tert-butyloxycarbonyl-tryptophanal 
• 882169-91-7 (S)-[2-(5-bromopyridin-3-yloxy)-1-(1H-indol-3-ylmethyl)ethyl]carbamic acid tert-butyl ester 
• 882170-23-2 [1-(3-bromo-phenoxymethyl)-2-(1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester 

Relevant articles and documents

Total syntheses of Hexahydropyrrolo[2,3-b]indole Alkaloids, (+)-pseudophrynamine 270 and (+)-pseudophrynamine 272A

A general strategy for asymmetric approach to the hexahydropyrrolo[2,3-b]indole alkaloids sharing a vicinal quaternary-tertiary centers has been disclosed via Pd(0)-catalyzed N-deacylative allylations (N-DaA) (dr > 20:1). Utilizing this strategy, asymmetric total syntheses of pseudophrynamines 270 (3c) and 272A (3b) have been achieved from a 3-substituted N-acyl indole 8 (pro-nucleophile) with allyl alcohol (pro-electrophile).

ANTIBODY DRUG CONJUGATES COMPRISING ECTEINASCIDIN DERIVATIVES

Drug conjugates having formula [D-(X) b -(AA) w -(T) g -(L)-] n -Ab wherein: D is a drug moiety having the following formula (I) or a pharmaceutically acceptable salt, ester, solvate, tautomer or stereoisomer th

A catalytic N-deacylative alkylation approach to hexahydropyrrolo[2,3-b]indole alkaloids

A versatile unprecedented strategy to diversely functionalized hexahydropyrrolo[2,3-b]indole alkaloids is described in high chemical yields. The synthesis features a key Pd(0)-catalyzed deacylative alkylation of N-acyl 3-substituted indoles using only 1 mol% of Pd(PPh3)4. The scope of this methodology is further defined in the asymmetric synthesis of pyrroloindolines using a diastereoselective approach.