tert-butyl (S)-2-((2R,3R,4Z)-1-((S)-2-benzamido-6-(2,3-bis(tertbutoxycarbonyl)guanidino)hexanoyl)-4-ethylidene-3-methylpyrrolidine-2-carboxamido)-4-methylpentanoate

Base Information

Chemical Name:tert-butyl (S)-2-((2R,3R,4Z)-1-((S)-2-benzamido-6-(2,3-bis(tertbutoxycarbonyl)guanidino)hexanoyl)-4-ethylidene-3-methylpyrrolidine-2-carboxamido)-4-methylpentanoate
CAS No.:1197285-77-0
Molecular Formula:C₄₂H₆₆N₆O₉
Molecular Weight:799.021
Hs Code.:

tert-butyl (S)-2-((2R,3R,4Z)-1-((S)-2-benzamido-6-(2,3-bis(tertbutoxycarbonyl)guanidino)hexanoyl)-4-ethylidene-3-methylpyrrolidine-2-carboxamido)-4-methylpentanoate

Synonyms:tert-butyl (S)-2-((2R,3R,4Z)-1-((S)-2-benzamido-6-(2,3-bis(tertbutoxycarbonyl)guanidino)hexanoyl)-4-ethylidene-3-methylpyrrolidine-2-carboxamido)-4-methylpentanoate

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Chemical Property of tert-butyl (S)-2-((2R,3R,4Z)-1-((S)-2-benzamido-6-(2,3-bis(tertbutoxycarbonyl)guanidino)hexanoyl)-4-ethylidene-3-methylpyrrolidine-2-carboxamido)-4-methylpentanoate

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Technology Process of tert-butyl (S)-2-((2R,3R,4Z)-1-((S)-2-benzamido-6-(2,3-bis(tertbutoxycarbonyl)guanidino)hexanoyl)-4-ethylidene-3-methylpyrrolidine-2-carboxamido)-4-methylpentanoate

There total 14 articles about tert-butyl (S)-2-((2R,3R,4Z)-1-((S)-2-benzamido-6-(2,3-bis(tertbutoxycarbonyl)guanidino)hexanoyl)-4-ethylidene-3-methylpyrrolidine-2-carboxamido)-4-methylpentanoate 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: 80.5%

: 1197285-76-9
tert-butyl (S)-2-((2R,3R,Z)-4-ethylidene-3-methylpyrrolidine-2-carboxamido)-4-methylpentanoate

: 1197285-65-6
(S)-2-benzamido-6-(2,3-bis(tert-butoxycarbonyl)guanidino)hexanoic acid

: 1197285-77-0
tert-butyl (S)-2-((2R,3R,4Z)-1-((S)-2-benzamido-6-(2,3-bis(tertbutoxycarbonyl)guanidino)hexanoyl)-4-ethylidene-3-methylpyrrolidine-2-carboxamido)-4-methylpentanoate

: tert-butyl (S)-2-((2R,3R,4Z)-1-((R)-2-benzamido-6-(2,3-bis(tertbutoxycarbonyl)guanidino)hexanoyl)-4-ethylidene-3-methylpyrrolidine-2-carboxamido)-4-methylpentanoate

Guidance literature:: With 2,3,5-trimethyl-pyridine; HATU; In dichloromethane; N,N-dimethyl-formamide; at 0 ℃; for 6h; optical yield given as %de; Inert atmosphere;
DOI:10.1021/jo902115s

Reference yield:

: 1197285-76-9
tert-butyl (S)-2-((2R,3R,Z)-4-ethylidene-3-methylpyrrolidine-2-carboxamido)-4-methylpentanoate

: 1197285-77-0
tert-butyl (S)-2-((2R,3R,4Z)-1-((S)-2-benzamido-6-(2,3-bis(tertbutoxycarbonyl)guanidino)hexanoyl)-4-ethylidene-3-methylpyrrolidine-2-carboxamido)-4-methylpentanoate

Guidance literature:: Multi-step reaction with 3 steps

1: triethylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one / tetrahydrofuran / 6 h / 0 °C

2: diethylamine / tetrahydrofuran / 5 h / 20 °C

3: dichloromethane / 1.5 h

With diethylamine; triethylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo201727g

Reference yield:

: 1337555-98-2
(Z)-3-[(tert-butyldiphenylsilyloxy)methyl]pent-3-en-2-yl 2-(tert-butoxycarbonylamino)acetate

: 1197285-77-0
tert-butyl (S)-2-((2R,3R,4Z)-1-((S)-2-benzamido-6-(2,3-bis(tertbutoxycarbonyl)guanidino)hexanoyl)-4-ethylidene-3-methylpyrrolidine-2-carboxamido)-4-methylpentanoate

Guidance literature:: Multi-step reaction with 9 steps

1: sodium hexamethyldisilazane / tetrahydrofuran / 0.33 h / 20 °C

2: benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine / acetonitrile / 20 h / 20 °C

3: pyridine; pyridine hydrofluoride / tetrahydrofuran / 5 h / 0 - 20 °C

4: methanesulfonyl chloride; triethylamine / dichloromethane / 18 h / 0 - 20 °C

5: dichloromethane / 3 h / 0 °C

6: potassium carbonate / acetone / 20 h / 20 °C

7: triethylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one / tetrahydrofuran / 6 h / 0 °C

8: diethylamine / tetrahydrofuran / 5 h / 20 °C

9: dichloromethane / 1.5 h

With pyridine; pyridine hydrofluoride; sodium hexamethyldisilazane; potassium carbonate; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; methanesulfonyl chloride; diethylamine; triethylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; In tetrahydrofuran; dichloromethane; acetone; acetonitrile; 1: enolate-Claisen rearrangement;
DOI:10.1021/jo201727g