N-BOC-S-trityl-cysteine

Base Information

• Chemical Name: N-BOC-S-trityl-cysteine
• CAS No.: 21947-98-8
• Molecular Formula: C₂₇H₂₉NO₄S
• Molecular Weight: 463.598
• Hs Code.: 2930 90 16
• NSC Number: 129903
• ChEMBL ID: CHEMBL409818
• Mol file: 21947-98-8.mol

Synonyms:EINECS 244-674-6;NSC 129903;N-BOC-S-trityl-cysteine;MFCD00038251;(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-tritylsulfanylpropanoic acid;NSC129903;CHEMBL409818;SCHEMBL1530926;N-|A-t.-Boc-S-trityl-D-cysteine;NSC-129903;PD196532;SY060193;FT-0638167;FT-0686528

Chemical Property of N-BOC-S-trityl-cysteine

Chemical Property:

• Appearance/Colour: White to yellow crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 143-146 °C(lit.)
• Refractive Index: 1.596
• Boiling Point: 610.9 °C at 760 mmHg
• PKA: 3.82±0.10(Predicted)
• Flash Point: 323.3 °C
• PSA: 100.93000
• Density: 1.2 g/cm³
• LogP: 6.08050
• Storage Temp.: 2-8°C
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 463.18172958
• Heavy Atom Count: 33
• Complexity: 583

Purity/Quality:

99% ^*data from raw suppliers

Boc-S-trityl-L-cysteine 99+% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CSC(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)C(=O)O

Technology Process of N-BOC-S-trityl-cysteine

There total 9 articles about N-BOC-S-trityl-cysteine 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: 90.0%

di-tert-butyl dicarbonate (24424-99-5) + S-trityl-L-cysteine (2799-07-7) → N-tert-butyloxycarbonyl-S-trityl-L-cysteine (21947-98-8,87494-13-1)

Guidance literature:

di-tert-butyl dicarbonate; S-trityl-L-cysteine; With sodium hydroxide; In water; at 20 ℃; for 24h;

With hydrogenchloride; In water; pH=2;

DOI:10.1016/j.ejmech.2012.02.018

Reference yield:

triphenylmethyl alcohol (76-84-6) → N-tert-butyloxycarbonyl-S-trityl-L-cysteine (21947-98-8,87494-13-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trifluoroacetic acid / 2 h

1.2: 0 °C / pH 5 - 6

2.1: sodium hydroxide / water / 24 h / 20 °C

2.2: pH 2

With trifluoroacetic acid; sodium hydroxide; In water;

DOI:10.1016/j.ejmech.2012.02.018

Reference yield:

trityl chloride (76-83-5) → N-tert-butyloxycarbonyl-S-trityl-L-cysteine (21947-98-8,87494-13-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / dimethylformamide / 48 h / 20 °C

2: Et₃N / methanol / 1.5 h / Heating

With triethylamine; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/ol0507524

upstream raw materials:

N-(tert-butyloxycarbonyl) azide

S-trityl-L-cysteine

triphenylmethyl alcohol

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

Downstream raw materials:

Boc-Cys(Trt)-ONp

C₁₆H₂₁NO₆S₂

N-Boc-S-trityl-L-cys-L-ala-OMe

Boc-Cys(Trt)-Gly-OCH₂Ph

Refernces

• 1、 Zhang, Junling,Li, Kui,Zhang, Qianru,Zhu, Zhimei,Huang, Gongchao,Tian, Hongqi. "Polycysteine as a new type of radio-protector ameliorated tissue injury through inhibiting ferroptosis in mice". . . Retrieved 2021/02/26.
• 2、 Forli, Stefano,Holcomb, Matthew,Peters, David S.,Romesberg, Floyd E.,Santos-Martins, Diogo,Tan, Yun Xuan,Walsh, Shawn I.. "Initial Analysis of the Arylomycin D Antibiotics". supporting information. p. 2112 - 2121. Retrieved 2020/08/10.