N-(N-cyclohexyl-N-methyl-O-t-butyl-(S)-α-glutamyl)-2(S)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine

Base Information

Chemical Name:N-(N-cyclohexyl-N-methyl-O-t-butyl-(S)-α-glutamyl)-2(S)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine
CAS No.:441772-06-1
Molecular Formula:C₃₉H₆₉N₅O₈
Molecular Weight:736.006
Hs Code.:

Synonyms:N-(N-cyclohexyl-N-methyl-O-t-butyl-(S)-α-glutamyl)-2(S)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine

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Chemical Property of N-(N-cyclohexyl-N-methyl-O-t-butyl-(S)-α-glutamyl)-2(S)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine

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Technology Process of N-(N-cyclohexyl-N-methyl-O-t-butyl-(S)-α-glutamyl)-2(S)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine

There total 11 articles about N-(N-cyclohexyl-N-methyl-O-t-butyl-(S)-α-glutamyl)-2(S)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine 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: 94.0%

: 50-00-0,30525-89-4,61233-19-0
formaldehyd

: 441772-05-0
N-(N-cyclohexyl-O-t-butyl-(S)-α-glutamyl)-2(S)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine

: 441772-06-1
N-(N-cyclohexyl-N-methyl-O-t-butyl-(S)-α-glutamyl)-2(S)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine

Guidance literature:: formaldehyd; N-(N-cyclohexyl-O-t-butyl-(S)-α-glutamyl)-2(S)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine; In dichloromethane; water; for 1h;

With sodium tris(acetoxy)borohydride; In dichloromethane; water; for 1h; Further stages.;
DOI:10.1021/jm011133d

Reference yield:

: 5382-16-1
4-HYDROXYPIPERIDINE

: 441772-06-1
N-(N-cyclohexyl-N-methyl-O-t-butyl-(S)-α-glutamyl)-2(S)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine

Guidance literature:: Multi-step reaction with 9 steps

1.1: 86 percent / CH₂Cl₂ / 56 h / 23 °C

2.1: NaH / dimethylformamide / 2 h

2.2: 61 percent / dimethylformamide / 18 h

3.1: 100 percent / HCl(gas) / CH₂Cl₂ / 1.25 h / 0 °C

4.1: 88 percent / Et₃N; HgCl₂ / CH₂Cl₂ / 20 h

5.1: 94 percent / H₂ / 10percent Pd/C / ethanol / 2.5 h / 23 °C / 3102.97 Torr

6.1: 67 percent / DIPEA; bromotris(pyrrolidino)phosphonium hexafluorophosphate / CH₂Cl₂ / 4 h / 0 - 23 °C

7.1: 91 percent / piperidine / tetrahydrofuran / 1 h

8.1: 88 percent / NaBH(OAc)3; AcOH / tetrahydrofuran / 2 h / 23 °C

9.1: CH₂Cl₂; H₂O / 1 h

9.2: 94 percent / NaBH(OAc)3 / CH₂Cl₂; H₂O / 1 h

With piperidine; hydrogenchloride; hydrogen; sodium tris(acetoxy)borohydride; sodium hydride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; mercury dichloride; 10percent Pd/C; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jm011133d

Reference yield:

: 322474-21-5
N,N'-bis-Boc-S-methyl-isothiourea

: 441772-06-1
N-(N-cyclohexyl-N-methyl-O-t-butyl-(S)-α-glutamyl)-2(S)-{2-[N-(N,N'-di-t-butoxycarbonylamidino)-4-piperidyloxy]ethyl}piperidine

Guidance literature:: Multi-step reaction with 6 steps

1.1: 88 percent / Et₃N; HgCl₂ / CH₂Cl₂ / 20 h

2.1: 94 percent / H₂ / 10percent Pd/C / ethanol / 2.5 h / 23 °C / 3102.97 Torr

3.1: 67 percent / DIPEA; bromotris(pyrrolidino)phosphonium hexafluorophosphate / CH₂Cl₂ / 4 h / 0 - 23 °C

4.1: 91 percent / piperidine / tetrahydrofuran / 1 h

5.1: 88 percent / NaBH(OAc)3; AcOH / tetrahydrofuran / 2 h / 23 °C

6.1: CH₂Cl₂; H₂O / 1 h

6.2: 94 percent / NaBH(OAc)3 / CH₂Cl₂; H₂O / 1 h

With piperidine; hydrogen; sodium tris(acetoxy)borohydride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; mercury dichloride; 10percent Pd/C; In tetrahydrofuran; ethanol; dichloromethane; water;
DOI:10.1021/jm011133d