tert-butyl 2-[(9S,10S,14S,18S)-7,16,19-triaza-10-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)-18-(carbamoylmethyl)-14-(naphthylmethyl)-8,17,20-trioxospiro[5.14]icos-11-en-9-yl]acetate

Base Information

Chemical Name:tert-butyl 2-[(9S,10S,14S,18S)-7,16,19-triaza-10-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)-18-(carbamoylmethyl)-14-(naphthylmethyl)-8,17,20-trioxospiro[5.14]icos-11-en-9-yl]acetate
CAS No.:495404-57-4
Molecular Formula:C₅₁H₇₁N₄O₉P
Molecular Weight:915.12
Hs Code.:

tert-butyl 2-[(9S,10S,14S,18S)-7,16,19-triaza-10-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)-18-(carbamoylmethyl)-14-(naphthylmethyl)-8,17,20-trioxospiro[5.14]icos-11-en-9-yl]acetate

Synonyms:tert-butyl 2-[(9S,10S,14S,18S)-7,16,19-triaza-10-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)-18-(carbamoylmethyl)-14-(naphthylmethyl)-8,17,20-trioxospiro[5.14]icos-11-en-9-yl]acetate

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Chemical Property of tert-butyl 2-[(9S,10S,14S,18S)-7,16,19-triaza-10-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)-18-(carbamoylmethyl)-14-(naphthylmethyl)-8,17,20-trioxospiro[5.14]icos-11-en-9-yl]acetate

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Technology Process of tert-butyl 2-[(9S,10S,14S,18S)-7,16,19-triaza-10-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)-18-(carbamoylmethyl)-14-(naphthylmethyl)-8,17,20-trioxospiro[5.14]icos-11-en-9-yl]acetate

There total 9 articles about tert-butyl 2-[(9S,10S,14S,18S)-7,16,19-triaza-10-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)-18-(carbamoylmethyl)-14-(naphthylmethyl)-8,17,20-trioxospiro[5.14]icos-11-en-9-yl]acetate 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: 87.0%

: 495404-50-7
tert-butyl 3-(N-{[N-((1S)-1-{N-[(2S)-2-(naphthylmethyl)pent-4-enyl]carbamoyl}-2-carbamoylethyl)carbamoyl]cyclohexyl}carbamoyl)-(3S,4S)-4-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)hex-5-enoate

: 495404-57-4
tert-butyl 2-[(9S,10S,14S,18S)-7,16,19-triaza-10-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)-18-(carbamoylmethyl)-14-(naphthylmethyl)-8,17,20-trioxospiro[5.14]icos-11-en-9-yl]acetate

Guidance literature:: With Grubbs catalyst first generation; In dichloromethane; Heating;
DOI:10.1021/jm0203635

Reference yield:

: 5292-43-3
bromoacetic acid tert-butyl ester

: 495404-57-4
tert-butyl 2-[(9S,10S,14S,18S)-7,16,19-triaza-10-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)-18-(carbamoylmethyl)-14-(naphthylmethyl)-8,17,20-trioxospiro[5.14]icos-11-en-9-yl]acetate

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaHMDS / tetrahydrofuran / 0.5 h / -78 °C

1.2: 77 percent / tetrahydrofuran / 2 h / -78 °C

2.1: 85 percent / aq. H₂O₂; aq. LiOH / tetrahydrofuran / 0 - 20 °C

3.1: 72 percent / HOAt; EDCI / dimethylformamide / 20 °C

4.1: 87 percent / (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / Heating

With lithium hydroxide; Grubbs catalyst first generation; 1-hydroxy-7-aza-benzotriazole; dihydrogen peroxide; sodium hexamethyldisilazane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm0203635

Reference yield:

: 162648-54-6
1-[((9H-fluoren-9-yl)methoxy)carbonylamino]cyclohexanecarboxylic acid

: 495404-57-4
tert-butyl 2-[(9S,10S,14S,18S)-7,16,19-triaza-10-(4-{[bis(tert-butoxy)phosphono]methyl}phenyl)-18-(carbamoylmethyl)-14-(naphthylmethyl)-8,17,20-trioxospiro[5.14]icos-11-en-9-yl]acetate

Guidance literature:: Multi-step reaction with 4 steps

1: 82 percent / HOBt; DIPCDI / dimethylformamide / 20 °C

2: piperidine / acetonitrile / 2 h / 20 °C

3: 72 percent / HOAt; EDCI / dimethylformamide / 20 °C

4: 87 percent / (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / Heating

With piperidine; Grubbs catalyst first generation; 1-hydroxy-7-aza-benzotriazole; 1,3-di-tert-butylcarbodiimide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jm0203635