Boc-L-thiocitrulline-otbu

Base Information

• Chemical Name: Boc-L-thiocitrulline-otbu
• CAS No.: 133565-49-8
• Molecular Formula: C₁₅H₂₉N₃O₄S
• Molecular Weight: 347.479
• DSSTox Substance ID: DTXSID20427154
• Wikidata: Q82239868
• Mol file: 133565-49-8.mol

Synonyms:BOC-L-THIOCITRULLINE-OTBU;133565-49-8;tert-butyl (2S)-5-(carbamothioylamino)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate;(S)-tert-Butyl 2-((tert-butoxycarbonyl)amino)-5-thioureidopentanoate;Boc-L-thiocitrulline t-butyl ester;Boc-L-thiocitrulline tert-Butyl Ester;SCHEMBL3698636;DTXSID20427154;MFCD00236875;AKOS015911332;BS-26573;Boc-L-thiocitrulline-OtBu (Boc-L-Orn(CSNH2)-OtBu);(S)-tert-Butyl2-((tert-butoxycarbonyl)amino)-5-thioureidopentanoate;L-Ornithine,n5-(aminothioxomethyl)-n2-[(1,1-dimethylethoxy)carbonyl]-,1,1-dimethylethylester

Chemical Property of Boc-L-thiocitrulline-otbu

Chemical Property:

• PSA: 142.80000
• LogP: 3.15080
• Storage Temp.: -15°C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 347.18787759
• Heavy Atom Count: 23
• Complexity: 427

Purity/Quality:

99% ^*data from raw suppliers

Boc-L-thiocitrullinetert-ButylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C(CCCNC(=S)N)NC(=O)OC(C)(C)C
• Isomeric SMILES: CC(C)(C)OC(=O)[C@H](CCCNC(=S)N)NC(=O)OC(C)(C)C
• Uses: Boc-L-thiocitrulline tert-Butyl Ester is an analogue of L-thiocitrulline as inhibitor of the isoforms of nitric oxide synthase (NOS).

Technology Process of Boc-L-thiocitrulline-otbu

There total 8 articles about Boc-L-thiocitrulline-otbu 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: 89.0%

thiophosgene (463-71-8) + tert-butyl (2S)-5-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate (53054-03-8) → Nα-(1,1-dimethylethoxycarbonyl)-Nδ-aminothiocarbonylornithine 1,1-dimethylethyl ester (133565-49-8)

Guidance literature:

thiophosgene; tert-butyl (2S)-5-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate; With calcium carbonate; In chloroform; water; for 16h;

With ammonia; In methanol; at 0 ℃; for 3h;

DOI:10.1016/S0968-0896(99)00136-4

Reference yield:

C15H27ClN2O4S (163761-83-9) → α-N-t-butoxycarbonyl-δ-(thioureido)-L-norvaline-t-butyl ester (133565-49-8)

Guidance literature:

With ammonia; In methanol; at 0 ℃; for 3h; Yield given;

Reference yield:

tert-butyl (2S)-5-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate (53054-03-8) → α-N-t-butoxycarbonyl-δ-(thioureido)-L-norvaline-t-butyl ester (133565-49-8)

Guidance literature:

Multi-step reaction with 2 steps

1: calcium carbonate / CHCl₃; H₂O

2: ammonia gas / methanol / 3 h / 0 °C

With ammonia; calcium carbonate; In methanol; chloroform; water;

upstream raw materials:

α-N-tert-butoxycarbonyl-δ-N-isothiocyanato-L-ornithine tert-butyl ester

C₁₅H₂₇ClN₂O₄S

tert-butyl (2S)-5-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate

thiophosgene

Downstream raw materials:

N^ω-Hydroxy-L-arginine dihydrochloride

α-N-t-butoxycarbonyl-N^G-benzyloxy-N^6'-t-butoxycarbonyl-L-arginine-t-butyl ester