(-)-N-(Diphenylmethylene)glycinyl-(2R)-bornane-10,2-sultam

Base Information

• Chemical Name: (-)-N-(Diphenylmethylene)glycinyl-(2R)-bornane-10,2-sultam
• CAS No.: 138566-17-3
• Molecular Formula: C25H28N2O3S
• Molecular Weight: 436.575
• Mol file: 138566-17-3.mol

Synonyms:Pentanedioyl dichloride,2-[(phenylsulfonyl)amino];2-(Benzenesulphonamido)glutaryl chloride;

Chemical Property of (-)-N-(Diphenylmethylene)glycinyl-(2R)-bornane-10,2-sultam

Chemical Property:

• PSA: 75.19000
• Density: 1.30
• LogP: 4.90960
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

1-((3AS,6R,7aR)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methano-benzo[c]isothiazol-1-yl)-2-((diphenylmethylene)amino)ethanone 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (-)-N-(Diphenylmethylene)glycinyl-(2R)-bornane-10,2-sultam

There total 2 articles about (-)-N-(Diphenylmethylene)glycinyl-(2R)-bornane-10,2-sultam 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%

ethyl N-diphenylmethylene glycine (69555-14-2) + (2R)-bornane-10,2-sultam (94594-90-8,124224-04-0) → 2-(benzhydrylideneamino)-1-(10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01.5]dec-4-yl)ethanone (138566-17-3)

Guidance literature:

(2R)-bornane-10,2-sultam; With trimethylaluminum; In hexane; toluene; at 20 ℃; for 0.25h; Inert atmosphere;

ethyl N-diphenylmethylene glycine; In hexane; toluene; at 40 ℃; for 20h; Time;

Reference yield:

methyl N-(diphenylmethylene)glycinate (81167-39-7) + (2R)-bornane-10,2-sultam (94594-90-8,124224-04-0) → 2-(benzhydrylideneamino)-1-(10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01.5]dec-4-yl)ethanone (138566-17-3)

Guidance literature:

With trimethylaluminum; Yield given. Multistep reaction; 1.) toluene, 2.) 50 deg C, 2 d;

DOI:10.1016/0040-4039(91)80217-T

Reference yield: 98.0%

2-(benzhydrylideneamino)-1-(10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01.5]dec-4-yl)ethanone (138566-17-3) + 1-fluoro-2,3-dimethoxy-5-chloromethylbenzene (102034-50-4) → (2R)-N-[(2S)-2-((diphenylmethylidene)amino)-2-(5'-fluoro-3',4'-dimethoxybenzyl)-ethan-1-oyl]bornane-10,2-sultam (476359-33-8)

Guidance literature:

With tetrabutylammomium bromide; potassium carbonate; In acetonitrile; at 50 ℃;

DOI:10.1016/S0957-4166(02)00321-X

upstream raw materials:

methyl N-(diphenylmethylene)glycinate

(2R)-bornane-10,2-sultam

ethyl N-diphenylmethylene glycine

Downstream raw materials:

N-(diphenylmethylene)-L-2-(9-fluorenyl)glycinesultam

N-(diphenylmethylene)-L-3,3-diphenylalaninesultam

(S)-2-(Benzhydrylidene-amino)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(2,6-dimethyl-phenyl)-propan-1-one

Refernces

• 1、 Josien, Hubert,Lavielle, Solange,Brunissen, Alie,Saffroy, Monique,Torrens, Yvette,et al.. "Design and Synthesis of Side-Chain Conformationally Restricted Phenylalanines and Their Use for Structure-Activity Studies on Tachykinin NK-1 Receptor". . p. 1586 - 1601. Retrieved 1994.
• 2、 He, Kailun,Zhu, Fangmeng,Li, Hua,Tang, Jian,Zhang, Xingxian. "An Efficient and Highly Asymmetric Synthesis of (S)-2’,6’-Dimethyltyrosine". . p. 510 - 516. Retrieved 2020/11/02.