(FMOC-CYS-OTBU)2, (DISULFIDE BOND)

Base Information

• Chemical Name: (FMOC-CYS-OTBU)2, (DISULFIDE BOND)
• CAS No.: 139592-37-3
• Molecular Formula: C44H48N2O8S2
• Molecular Weight: 797.006
• Mol file: 139592-37-3.mol

Synonyms:(FMOC-CYS-OTBU)2;(FMOC-CYS-OTBU)2, (DISULFIDE BOND)

Chemical Property of (FMOC-CYS-OTBU)2, (DISULFIDE BOND)

Chemical Property:

• PSA: 179.86000
• LogP: 9.64760
• Storage Temp.: Store at 0-5°C

Purity/Quality:

98.5% ^*data from raw suppliers

(2R)-tert-Butyl2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(((2R)-3-(tert-butoxy)-2-((((1,2,3,3a,8,8a-hexahydrocyclopenta[a]inden-8-yl)methoxy)carbonyl)amino)-3-oxopropyl)disulfanyl)propanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (2R)-tert-Butyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(((2R)-3-(tert-butoxy)-2-((((1,2,3,3a,8,8a-hexahydrocyclopenta[a]inden-8-yl)methoxy)carbonyl)amino)-3-oxopropyl)disulfanyl)propanoate is a useful research chemical.

Technology Process of (FMOC-CYS-OTBU)2, (DISULFIDE BOND)

There total 9 articles about (FMOC-CYS-OTBU)2, (DISULFIDE BOND) 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: 82.0%

L-cystine tert-butyl ester (62574-13-4) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → (2R,2‘R)-di-tert-butyl 3,3‘-disulfanediylbis(2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)propanoate) (139592-37-3)

Guidance literature:

With 4-methyl-morpholine; In tetrahydrofuran; at 20 ℃; for 14h;

DOI:10.1021/acs.jmedchem.9b01044

Reference yield: 81.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + L-cystine tert-butyl ester (62574-13-4) → (2R,2‘R)-di-tert-butyl 3,3‘-disulfanediylbis(2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)propanoate) (139592-37-3)

Guidance literature:

With 4-methyl-morpholine; In tetrahydrofuran; for 3h; cooling;

DOI:10.1021/jo0346398

Reference yield: 75.0%

L-Cystine tert-butyl ester + 9-fluorenylmethyl-N-succinimidyl carbonate → (2R,2‘R)-di-tert-butyl 3,3‘-disulfanediylbis(2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)propanoate) (139592-37-3)

Guidance literature:

With 4-methyl-morpholine; In tetrahydrofuran; at 0 - 20 ℃; for 18h;

upstream raw materials:

L-cystine tert-butyl ester

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(fluorenylmethoxy)carbonyl chloride

acetic acid tert-butyl ester

Downstream raw materials:

(2S,6R)-N²-triphenylmethyl-N⁶-(9H-fluorenylmethoxycarbonyl)-lanthionine O¹-allyl-O⁷-tert-butyl ester

benzyl (-)-(2S)-1-trityl-aziridine-2-carboxylate

(R)-3-[(R)-2-tert-Butoxycarbonyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-ethylsulfanyl]-2-(trityl-amino)-propionic acid benzyl ester

N-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-((R)-2,3-bis(palmitoyloxy)propyl)-L-cysteine

Refernces

• 1、 Owens, Andrew E.,De Paola, Ivan,Hansen, William A.,Liu, Yi-Wen,Khare, Sagar D.,Fasan, Rudi. "Design and Evolution of a Macrocyclic Peptide Inhibitor of the Sonic Hedgehog/Patched Interaction". . p. 12559 - 12568. Retrieved 2017.
• 2、 Lu, Benjamin L.,Williams, Geoffrey M.,Verdon, Daniel J.,Dunbar, P. Rod,Brimble, Margaret A.. "Synthesis and Evaluation of Novel TLR2 Agonists as Potential Adjuvants for Cancer Vaccines". supporting information. p. 2282 - 2291. Retrieved 2019/10/02.