tetrahydro-2H-pyran-4-yl (6S,7S)-7-((hydroxyamino)carbonyl)-6-((4-phenylpiperazin-1-yl)carbonyl)-5-azaspiro(2,5)octane-5-carboxylate

Base Information

• Chemical Name: tetrahydro-2H-pyran-4-yl (6S,7S)-7-((hydroxyamino)carbonyl)-6-((4-phenylpiperazin-1-yl)carbonyl)-5-azaspiro(2,5)octane-5-carboxylate
• CAS No.: 791828-53-0
• Molecular Formula: C₂₅H₃₄N₄O₆
• Molecular Weight: 486.568
• Mol file: 791828-53-0.mol

Synonyms:tetrahydro-2H-pyran-4-yl (6S,7S)-7-((hydroxyamino)carbonyl)-6-((4-phenylpiperazin-1-yl)carbonyl)-5-azaspiro(2,5)octane-5-carboxylate

Chemical Property of tetrahydro-2H-pyran-4-yl (6S,7S)-7-((hydroxyamino)carbonyl)-6-((4-phenylpiperazin-1-yl)carbonyl)-5-azaspiro(2,5)octane-5-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tetrahydro-2H-pyran-4-yl (6S,7S)-7-((hydroxyamino)carbonyl)-6-((4-phenylpiperazin-1-yl)carbonyl)-5-azaspiro(2,5)octane-5-carboxylate

There total 7 articles about tetrahydro-2H-pyran-4-yl (6S,7S)-7-((hydroxyamino)carbonyl)-6-((4-phenylpiperazin-1-yl)carbonyl)-5-azaspiro(2,5)octane-5-carboxylate 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:

tetrahydro-2H-pyran-4-yl (6S,7S)-7-(((benzyloxy)amino)carbonyl)-6-((4-phenylpiperazin-1-yl)carbonyl)-5-azaspiro(2,5)octane-5-carboxylate → tetrahydro-2H-pyran-4-yl (6S,7S)-7-((hydroxyamino)carbonyl)-6-((4-phenylpiperazin-1-yl)carbonyl)-5-azaspiro(2,5)octane-5-carboxylate (791828-53-0)

Guidance literature:

With 5% palladium on barium sulphate; hydrogen; In methanol; for 1.5h; under 760.051 Torr;

Reference yield:

C25H33N3O6 → tetrahydro-2H-pyran-4-yl (6S,7S)-7-((hydroxyamino)carbonyl)-6-((4-phenylpiperazin-1-yl)carbonyl)-5-azaspiro(2,5)octane-5-carboxylate (791828-53-0)

Guidance literature:

With hydroxylamine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2007.10.108

Reference yield:

(6S,7S)-6-((4-phenylpiperazin-1-yl)carbonyl)-5-azaspiro(2,5)octane-7-carboxylic acid (791834-68-9) → tetrahydro-2H-pyran-4-yl (6S,7S)-7-((hydroxyamino)carbonyl)-6-((4-phenylpiperazin-1-yl)carbonyl)-5-azaspiro(2,5)octane-5-carboxylate (791828-53-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 0.08 h / 0 °C

1.2: 3 h / 20 °C

2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 24 h / 20 °C

3.1: 5% palladium on barium sulphate; hydrogen / methanol / 1.5 h / 760.05 Torr

With 5% palladium on barium sulphate; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

upstream raw materials:

(6S,7S)-6-((4-phenylpiperazin-1-yl)carbonyl)-5-azaspiro(2,5)octane-7-carboxylic acid

(6S,7S)-7-(tert-butoxycarbonyl)-5-azaspiro[2,5]octane-6-carboxylic acid

4-phenyl-1-piperazine

tert-butyl (6S,7S)-6-((4-phenylpiperazin-1-yl)carbonyl)-5-azaspiro(2,5)octane-7-carboxylate

Refernces

• 1、 Yao, Wenqing,Zhuo, Jincong,Burns, David M.,Li, Yun-Long,Qian, Ding-Quan,Zhang, Colin,He, Chunhong,Xu, Meizhong,Shi, Eric,Li, Yanlong,Marando, Cindy A.,Covington, Maryanne B.,Yang, Gengjie,Liu, Xiangdong,Pan, Max,Fridman, Jordan S.,Scherle, Peggy,Wasserman, Zelda R.,Hollis, Gregory,Vaddi, Kris,Yeleswaram, Swamy,Newton, Robert,Friedman, Steve,Metcalf, Brian. "Design and identification of selective HER-2 sheddase inhibitors via P1′ manipulation and unconventional P2′ perturbations to induce a molecular metamorphosis". . p. 159 - 163. Retrieved 2008/09/19.