(S)-methyl 2-((3S,6S)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-3-isopropyl-2-oxopiperazin-1-yl)-3-(1H-indol-3-yl)propanoate

Base Information

Chemical Name:(S)-methyl 2-((3S,6S)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-3-isopropyl-2-oxopiperazin-1-yl)-3-(1H-indol-3-yl)propanoate
CAS No.:1613043-88-1
Molecular Formula:C₃₆H₄₅N₃O₄Si
Molecular Weight:611.856
Hs Code.:

Synonyms:(S)-methyl 2-((3S,6S)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-3-isopropyl-2-oxopiperazin-1-yl)-3-(1H-indol-3-yl)propanoate

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Chemical Property of (S)-methyl 2-((3S,6S)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-3-isopropyl-2-oxopiperazin-1-yl)-3-(1H-indol-3-yl)propanoate

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Technology Process of (S)-methyl 2-((3S,6S)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-3-isopropyl-2-oxopiperazin-1-yl)-3-(1H-indol-3-yl)propanoate

There total 1 articles about (S)-methyl 2-((3S,6S)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-3-isopropyl-2-oxopiperazin-1-yl)-3-(1H-indol-3-yl)propanoate 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: 59.0%

: 1613043-85-8
(S)-benzyl 2-(((S)-2-(((S)-3-(1H-indol-3-yl)-1-methoxy-1-oxopropan-2-yl)amino)-3-((tert-butyldiphenylsilyl)-oxy)propyl)(4-methoxybenzyl)amino)-3-methylbutanoate

: 1613043-88-1
(S)-methyl 2-((3S,6S)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-3-isopropyl-2-oxopiperazin-1-yl)-3-(1H-indol-3-yl)propanoate

: (S)-methyl 2-((3S,6S)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-3-isopropyl-4-(4-methoxybenzyl)-2-oxopiperazin-1-yl)-3-(1H-indol-3-yl)propanoate

Guidance literature:: (S)-benzyl 2-(((S)-2-(((S)-3-(1H-indol-3-yl)-1-methoxy-1-oxopropan-2-yl)amino)-3-((tert-butyldiphenylsilyl)-oxy)propyl)(4-methoxybenzyl)amino)-3-methylbutanoate; With palladium hydroxide, 20 wt% on carbon; hydrogen; In ethanol; for 9h;

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In acetonitrile; at 20 ℃; for 24h;
DOI:10.1002/ejoc.201301773

Reference yield: 70.0%

: 1613043-88-1
(S)-methyl 2-((3S,6S)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-3-isopropyl-2-oxopiperazin-1-yl)-3-(1H-indol-3-yl)propanoate

: 71989-33-8
Fmoc-Ser(tBu)-OH

: (S)-methyl 2-((3S,6S)-4-((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(tert-butoxy)propanoyl)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-3-isopropyl-2-oxopiperazin-1-yl)-3-(1H-indol-3-yl)propanoate

Guidance literature:: With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 40 ℃; for 21h;
DOI:10.1002/ejoc.201301773

Reference yield:

: 1613043-88-1
(S)-methyl 2-((3S,6S)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-3-isopropyl-2-oxopiperazin-1-yl)-3-(1H-indol-3-yl)propanoate

: ((2S,5S)-1-((S)-1-((2-amino-2-oxoethyl)amino)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)-4-((6S,9S,12S)-9-benzyl-6-(4-(tert-butoxy)benzyl)-12-(tert-butoxymethyl)-2,2-dimethyl-4,7,10-trioxo-3-oxa-5,8,11-triazatridecan-13-oyl)-5-isopropyl-6-oxopiperazin-2-yl)methyl methanesulfonate

Guidance literature:: Multi-step reaction with 7 steps

1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 21 h / 40 °C

2: piperidine / N,N-dimethyl-formamide / 2 h / 20 °C

3: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / acetonitrile / 18 h / 20 °C

4: lithium hydroxide / methanol; tetrahydrofuran; water / 13 h / 20 °C

5: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 2 °C

6: tetrabutyl ammonium fluoride / tetrahydrofuran / 19 h / 0 °C

7: triethylamine / dichloromethane / 0.5 h / 20 °C

With piperidine; tetrabutyl ammonium fluoride; triethylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; lithium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/ejoc.201301773