Boc-S-trityl-D-cysteine

Base Information

• Chemical Name: Boc-S-trityl-D-cysteine
• CAS No.: 87494-13-1
• Molecular Formula: C₂₇H₂₉NO₄S
• Molecular Weight: 463.598
• Mol file: 87494-13-1.mol

Synonyms:boc-d-cys(trt)-oh;N-Boc-S-Trityl-L-Cysteine;N-t-butoxycarbonyl-S-trityl-L-Cysteine;N-[(1,1-dimethylethoxy)carbonyl]-S-trityl-L-cysteine;Boc-S-Trityl-D-Cysteine;Boc-Cys(Trt);S-trityl-N-Boc-(R)-cysteine;AmbotzBAA5000;N-t-butyloxycarbonyl-S-trityl-L-cysteine;S-trityl-N-Boc-cysteine;

Chemical Property of Boc-S-trityl-D-cysteine

Chemical Property:

• Refractive Index: 1.599
• Boiling Point: 610.922 °C at 760 mmHg
• PKA: 3.82±0.10(Predicted)
• Flash Point: 323.274 °C
• PSA: 100.93000
• Density: 1.201 g/cm³
• LogP: 6.08050
• Storage Temp.: Store at 0°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Ethanol (Sparingly)

Purity/Quality:

99% ^*data from raw suppliers

Boc-D-Cys(Trt)-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Boc-Cys(Trt)-OH is used in method for preparing ularitide.

Technology Process of Boc-S-trityl-D-cysteine

There total 9 articles about Boc-S-trityl-D-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:

(R)-2-tert-Butoxycarbonylamino-3-tritylsulfanyl-propionic acid 2-hydroxy-ethyl ester

4-[4-((R)-2-tert-Butoxycarbonylamino-3-tritylsulfanyl-propionylamino)-phenoxy]-benzoic acid methyl ester

{(R)-2-[4-(3-Bromo-8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-yl)-piperazin-1-yl]-2-oxo-1-tritylsulfanylmethyl-ethyl}-carbamic acid tert-butyl ester

[(R)-2-(4-{2-[4-(3-Bromo-8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-yl)-piperazin-1-yl]-2-oxo-ethyl}-piperidin-1-yl)-2-oxo-1-tritylsulfanylmethyl-ethyl]-carbamic acid tert-butyl ester

Refernces

• 1、 Ali, Rafat,Chattopadhyay, Naibedya,Kulkarni, Chirag,Kulkarni, Manish M.,Porwal, Konica,Sharma, Swati,Tewari, Deepshikha,Verma, Sandeep. "Tripeptide-induced modulation of mesenchymal stem cell biomechanics stimulates proliferation and wound healing". supporting information. p. 3043 - 3046. Retrieved 2020/03/18.
• 2、 Yamada, Takeshi,Miki, Shouta,Ni, Lu,Nakatani, Kazuhiko. "CGG repeat DNA assisted dimerization of CGG/CGG binding molecule through intermolecular disulfide formation". . p. 13072 - 13075. Retrieved 2018/11/30.