(9H-fluoren-9-yl)methyl (S)-1-isothiocyanato-3-phenylpropan-2-ylcarbamate

Base Information

• Chemical Name: (9H-fluoren-9-yl)methyl (S)-1-isothiocyanato-3-phenylpropan-2-ylcarbamate
• CAS No.: 1172596-64-3
• Molecular Formula: C₂₅H₂₂N₂O₂S
• Molecular Weight: 414.528
• Mol file: 1172596-64-3.mol

Synonyms:(9H-fluoren-9-yl)methyl (S)-1-isothiocyanato-3-phenylpropan-2-ylcarbamate

Chemical Property of (9H-fluoren-9-yl)methyl (S)-1-isothiocyanato-3-phenylpropan-2-ylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (9H-fluoren-9-yl)methyl (S)-1-isothiocyanato-3-phenylpropan-2-ylcarbamate

There total 5 articles about (9H-fluoren-9-yl)methyl (S)-1-isothiocyanato-3-phenylpropan-2-ylcarbamate 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: 93.0%

carbon disulfide (75-15-0,12122-00-8) + (1-aminomethyl-2-phenyl-ethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester; hydrochloride → (9H-fluoren-9-yl)methyl (S)-1-isothiocyanato-3-phenylpropan-2-ylcarbamate (1172596-64-3)

Guidance literature:

carbon disulfide; (1-aminomethyl-2-phenyl-ethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester; hydrochloride; With triethylamine; In tetrahydrofuran; Cooling with ice;

With p-toluenesulfonyl chloride; In tetrahydrofuran; Cooling;

DOI:10.1021/jo900675s

Reference yield:

(S)-2-(N-fluorenylmethoxycarbonylamino)-3-phenyl-iodopropane (161529-17-5) → (9H-fluoren-9-yl)methyl (S)-1-isothiocyanato-3-phenylpropan-2-ylcarbamate (1172596-64-3)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium azide / N,N-dimethyl-formamide / 6 h / 20 °C

2: tetrahydrofuran / 0.5 h / Reflux

3: tetrahydrofuran / 1 h / Reflux

With sodium azide; In tetrahydrofuran; N,N-dimethyl-formamide; 2: |Staudinger Azide Reduction / 3: |Aza-Wittig Reaction;

DOI:10.1039/c8ob01061g

Reference yield:

N-Fmoc L-Phe (35661-40-6) → (9H-fluoren-9-yl)methyl (S)-1-isothiocyanato-3-phenylpropan-2-ylcarbamate (1172596-64-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 4-methyl-morpholine; chloroformic acid ethyl ester / tetrahydrofuran / 0.25 h / -15 °C

1.2: 0.5 h

1.3: 0.25 h

2.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 6 h

3.1: sodium azide / N,N-dimethyl-formamide / 6 h / 20 °C

4.1: tetrahydrofuran / 0.5 h / Reflux

5.1: tetrahydrofuran / 1 h / Reflux

With 4-methyl-morpholine; 1H-imidazole; sodium azide; iodine; chloroformic acid ethyl ester; triphenylphosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 4.1: |Staudinger Azide Reduction / 5.1: |Aza-Wittig Reaction;

DOI:10.1039/c8ob01061g

upstream raw materials:

carbon disulfide

(S)-2-(N-fluorenylmethoxycarbonylamino)-3-phenyl-iodopropane

(9-fluorenylmethoxycarbonyl)-L-phenylalaninol

N-Fmoc L-Phe

Downstream raw materials:

(9H-fluoren-9-yl)methyl (S)-3-phenyl-1-(3-((S)-1-phenylethyl)thioureido)propan-2-ylcarbamate

(9H-fluoren-9-yl)methyl (S)-3-phenyl-1-(3-((R)-1-phenylethyl)thioureido)propan-2-ylcarbamate

methyl (S)-3-(3-(2-(((9H-fluoren-9-yl)methoxy)carbonyl)amino-3-phenylpropyl)thioureido)propanoate

methyl (S)-2-(3-(2-(((9H-fluoren-9-yl)methoxy)carbonyl)amino-(S)-3-phenylpropyl)thioureido)propanoate

Refernces

• 1、 Sureshbabu, Vommina V.,Naik, Shankar A.,Hemantha,Narendra,Das, Ushati,Guru Row, Tayur N.. "N-urethane-protected amino alkyl isothiocyanates: Synthesis, isolation, characterization, and application to the synthesis of thioureidopeptides". supporting information; experimental part. p. 5260 - 5266. Retrieved 2009/12/06.