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247068-84-4

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247068-84-4 Usage

Description

(S)-2-amino-4-methyl-1-((R)-2-methyloxiran-2-yl)pentan-1-one, also known as (S)-4-methyl-1-(2-methyloxiran-2-yl)pentan-2-amine, is a chiral compound characterized by the presence of an amino group and a ketone group attached to a pentane chain. The molecule features a methyl group at the fourth position and a stereocenter at the second position, which is designated as the (R) configuration. This chemical is widely recognized for its utility as a building block in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals, making it a high-value intermediate in organic synthesis. Its pharmaceutical properties and unique structure contribute to its use in the research and development of new drugs and therapeutic compounds, as well as its role as a valuable tool in the study of organic chemistry and drug discovery.

Uses

Used in Pharmaceutical Industry:
(S)-2-amino-4-methyl-1-((R)-2-methyloxiran-2-yl)pentan-1-one is used as a key intermediate in the synthesis of various pharmaceuticals for its potential to contribute to the development of new drugs and therapeutic compounds. Its unique structure and reactivity allow for the creation of molecules with specific biological activities, making it a valuable asset in drug discovery and medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, (S)-2-amino-4-methyl-1-((R)-2-methyloxiran-2-yl)pentan-1-one is utilized as a building block for the synthesis of agrochemicals, including pesticides and herbicides. Its chiral nature and functional groups enable the development of targeted and effective compounds for agricultural applications.
Used in Organic Synthesis Research:
(S)-2-amino-4-methyl-1-((R)-2-methyloxiran-2-yl)pentan-1-one serves as a valuable tool in the field of organic synthesis research. Its unique structure allows researchers to explore new synthetic pathways and develop innovative methods for the preparation of complex organic molecules, contributing to the advancement of organic chemistry.
Used in Drug Discovery:
This chiral compound is employed in drug discovery processes to identify and optimize potential drug candidates. Its presence in the synthesis of various compounds aids in the investigation of their pharmacological properties and potential therapeutic applications, thus playing a crucial role in the development of novel treatments for various diseases and conditions.

Check Digit Verification of cas no

The CAS Registry Mumber 247068-84-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,4,7,0,6 and 8 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 247068-84:
(8*2)+(7*4)+(6*7)+(5*0)+(4*6)+(3*8)+(2*8)+(1*4)=154
154 % 10 = 4
So 247068-84-4 is a valid CAS Registry Number.

247068-84-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name (5)-2-amino-4-methyl-1-((R)-2-methyloxiran-2-yl)pentan-1-one

1.2 Other means of identification

Product number -
Other names (S)-2-aMino-4-Methyl-1-((R)-2-Methyloxiran-2-yl)pentan-1-one

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:247068-84-4 SDS

247068-84-4Synthetic route

tert-butyl ((2S)-4-methyl-1-((2R)-2-methyloxirane-2-yl)-1-oxopentan-2-yl)carbamate
247068-82-2

tert-butyl ((2S)-4-methyl-1-((2R)-2-methyloxirane-2-yl)-1-oxopentan-2-yl)carbamate

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

Conditions
ConditionsYield
With trifluoroacetic acid at 20℃; for 0.0333333 - 0.333333h;
With trifluoroacetic acid In dichloromethane at 25℃; for 1.5h; Inert atmosphere;
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 1h;
N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / dichloromethane / 3 h / 25 °C / Inert atmosphere
2: tetrahydrofuran / 6 h / 0 °C / Inert atmosphere
3: potassium peroxymonosulfate; 1,1,1-trifluoro-2-propanone; sodium hydrogencarbonate / water; acetonitrile / Inert atmosphere
4: trifluoroacetic acid / dichloromethane / 1.5 h / 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 6 steps
1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.5 h / 0 °C
1.2: 3 h / 0 °C
2.1: tetrahydrofuran / 0 °C / Inert atmosphere
3.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol; tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 °C
5.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere
6.1: trifluoroacetic acid / dichloromethane / 1 h / 0 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: 4-methyl-morpholine; chloroformic acid ethyl ester / dichloromethane / 0.33 h / -15 - -10 °C / Inert atmosphere
1.2: 2 h / -15 - -10 °C
2.1: magnesium; iodine / tetrahydrofuran / 2.5 h / 50 - 55 °C / Inert atmosphere
2.2: 8.25 h / 0 - 30 °C
3.1: potassium carbonate; benzonitrile; dihydrogen peroxide / methanol / 6 h / 25 - 30 °C
4.1: trifluoroacetic acid / dichloromethane / 3 h / 5 - 10 °C / Inert atmosphere
View Scheme
N-(tert-butoxycarbonyl)-L-leucine-N'-methoxy-N'-methylamide
87694-50-6

N-(tert-butoxycarbonyl)-L-leucine-N'-methoxy-N'-methylamide

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tetrahydrofuran / 6 h / 0 °C / Inert atmosphere
2: potassium peroxymonosulfate; 1,1,1-trifluoro-2-propanone; sodium hydrogencarbonate / water; acetonitrile / Inert atmosphere
3: trifluoroacetic acid / dichloromethane / 1.5 h / 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1: tetrahydrofuran / 0 °C / Inert atmosphere
2: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol; tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 °C
4: Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere
5: trifluoroacetic acid / dichloromethane / 1 h / 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1: tetrahydrofuran / 6 h / 0 °C / Inert atmosphere
2: sodium hydrogencarbonate; Oxone; 1,1,1-trifluoro-2-propanone / water; acetonitrile / 1.5 h / -10 °C / Inert atmosphere
3: trifluoroacetic acid / dichloromethane / 1.5 h / 25 °C / Inert atmosphere
View Scheme
tert-butyl [(1S)-3-methyl-1-(2-methylpropyl)-2-oxobut-3-en-1-yl]carbamate
247068-81-1

tert-butyl [(1S)-3-methyl-1-(2-methylpropyl)-2-oxobut-3-en-1-yl]carbamate

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol; tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 °C
3: Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere
4: trifluoroacetic acid / dichloromethane / 1 h / 0 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium hydrogencarbonate; Oxone; 1,1,1-trifluoro-2-propanone / water; acetonitrile / 1.5 h / -10 °C / Inert atmosphere
2: trifluoroacetic acid / dichloromethane / 1.5 h / 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate; benzonitrile; dihydrogen peroxide / methanol / 6 h / 25 - 30 °C
2: trifluoroacetic acid / dichloromethane / 3 h / 5 - 10 °C / Inert atmosphere
View Scheme
tert-butyl N-[(4S)-3-hydroxy-2,6-dimethylhept-1-en-4-yl]carbamate
1609959-45-6

tert-butyl N-[(4S)-3-hydroxy-2,6-dimethylhept-1-en-4-yl]carbamate

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 °C
2: Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere
3: trifluoroacetic acid / dichloromethane / 1 h / 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 °C
2: Dess-Martin periodane / dichloromethane / 10 h / 0 °C / Inert atmosphere
3: trifluoroacetic acid / dichloromethane / 0 - 20 °C
View Scheme
tert-butyl N-[(2S)-1-(-2-methyloxirane-2-yl)-1-hydroxy-4-methylpentan-2-yl]carbamate
1609959-47-8

tert-butyl N-[(2S)-1-(-2-methyloxirane-2-yl)-1-hydroxy-4-methylpentan-2-yl]carbamate

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere
2: trifluoroacetic acid / dichloromethane / 1 h / 0 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: Dess-Martin periodane / dichloromethane / 10 h / 0 °C / Inert atmosphere
2: trifluoroacetic acid / dichloromethane / 0 - 20 °C
View Scheme
L-leucine
61-90-5

L-leucine

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sodium hydroxide / water / 20 h / 25 - 30 °C
2.1: 4-methyl-morpholine; chloroformic acid ethyl ester / dichloromethane / 0.33 h / -15 - -10 °C / Inert atmosphere
2.2: 2 h / -15 - -10 °C
3.1: magnesium; iodine / tetrahydrofuran / 2.5 h / 50 - 55 °C / Inert atmosphere
3.2: 8.25 h / 0 - 30 °C
4.1: potassium carbonate; benzonitrile; dihydrogen peroxide / methanol / 6 h / 25 - 30 °C
5.1: trifluoroacetic acid / dichloromethane / 3 h / 5 - 10 °C / Inert atmosphere
View Scheme
3-(tert-butoxycarbonylamino)-3-phenylpropanoic acid
14676-01-8

3-(tert-butoxycarbonylamino)-3-phenylpropanoic acid

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

tert-butyl 3-[(2S)-4-methyl-1-((2R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino]-3-oxo-1-phenylpropylcarbamate
1609959-50-3

tert-butyl 3-[(2S)-4-methyl-1-((2R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino]-3-oxo-1-phenylpropylcarbamate

Conditions
ConditionsYield
Stage #1: 3-(tert-butoxycarbonylamino)-3-phenylpropanoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h;
Stage #2: (2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one With N-ethyl-N,N-diisopropylamine In dichloromethane for 3h;
92%
N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

tert-butyl ((S)-1-(((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate
1469983-01-4

tert-butyl ((S)-1-(((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate

Conditions
ConditionsYield
Stage #1: N-tert-butoxycarbonyl-L-phenylalanine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h;
Stage #2: (2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one With N-ethyl-N,N-diisopropylamine In dichloromethane for 3h;
87%
Stage #1: (2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h;
Stage #2: N-tert-butoxycarbonyl-L-phenylalanine With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 3h;
87%
N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

tert-butyl ((S)-4-methyl-1-(((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)amino)-1-oxopentan-2-yl)carbamate

tert-butyl ((S)-4-methyl-1-(((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)amino)-1-oxopentan-2-yl)carbamate

Conditions
ConditionsYield
Stage #1: (2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h;
Stage #2: N-tert-butoxycarbonyl-L-leucine With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 3h;
76%
C17H30N8O4
1644406-04-1

C17H30N8O4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

C26H43N7O6
1620107-53-0

C26H43N7O6

Conditions
ConditionsYield
Stage #1: C17H30N8O4 With hydrogenchloride; tert.-butylnitrite In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide at -30℃; for 3h;
Stage #2: (2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at -30 - 20℃;
67%
C22H31N3O5

C22H31N3O5

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

(S)-1-(2-acetamidoacetyl)-N-((S)-3-(4-tert-butylphenyl)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-1-oxopropan-2-yl)pyrrolidine-2-carboxamide

(S)-1-(2-acetamidoacetyl)-N-((S)-3-(4-tert-butylphenyl)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-1-oxopropan-2-yl)pyrrolidine-2-carboxamide

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;64%
C19H20Cl2N2O4

C19H20Cl2N2O4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

2,5-dichloro-N-[5-methyl-1-(4-methyl-1-{(S)-4-methyl-1-[(R)-2-methyloxiran-2-yl]-1-oxopentan-2-ylamino}-1-oxopentan-2-yl)-2-oxo-1,2-dihydropyridin-3-yl]benzamide

2,5-dichloro-N-[5-methyl-1-(4-methyl-1-{(S)-4-methyl-1-[(R)-2-methyloxiran-2-yl]-1-oxopentan-2-ylamino}-1-oxopentan-2-yl)-2-oxo-1,2-dihydropyridin-3-yl]benzamide

Conditions
ConditionsYield
With 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); N-ethyl-N,N-diisopropylamine In dichloromethane for 6h; Inert atmosphere;58%
(S)-4-methoxybenzyl 2-((S)-4-methyl-2-((S)-N-(((2-methyl-2-(prop-2-yn-1-yloxy)propanoyl)oxy)methyl)-2-(2-morpholinoacetamido)-4-pheylbutanamido)pentanamido)-3-phenylpropanoate trifluoroacetic acid salt

(S)-4-methoxybenzyl 2-((S)-4-methyl-2-((S)-N-(((2-methyl-2-(prop-2-yn-1-yloxy)propanoyl)oxy)methyl)-2-(2-morpholinoacetamido)-4-pheylbutanamido)pentanamido)-3-phenylpropanoate trifluoroacetic acid salt

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

((S)-N-((S)-4-methyl-1-(((S)-1-(((S)-4-methyl-1-((R)-2-methyioxiran-2-yl)-1-oxopentan-2-yl)amino)-1-oxo-3-phenylpropan-2-yi)amino)-1-oxopentan-2-yl)-2-(2-morphoiinoacetamido)-4-phenyibutanamido)methyl2-methyl-2-(prop-2-yn-1-yloxy)propanoate

((S)-N-((S)-4-methyl-1-(((S)-1-(((S)-4-methyl-1-((R)-2-methyioxiran-2-yl)-1-oxopentan-2-yl)amino)-1-oxo-3-phenylpropan-2-yi)amino)-1-oxopentan-2-yl)-2-(2-morphoiinoacetamido)-4-phenyibutanamido)methyl2-methyl-2-(prop-2-yn-1-yloxy)propanoate

Conditions
ConditionsYield
With 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium In dichloromethane at 0 - 20℃; for 4h;56.6%
C15H26N8O4
1644401-94-4

C15H26N8O4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

C24H39N7O6
1620107-52-9

C24H39N7O6

Conditions
ConditionsYield
Stage #1: C15H26N8O4 With hydrogenchloride; tert.-butylnitrite In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide at -30℃; for 3h;
Stage #2: (2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at -30 - 20℃;
55%
Boc-homoPhe-Leu-Phe-NHNH2

Boc-homoPhe-Leu-Phe-NHNH2

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

C39H56N4O7

C39H56N4O7

Conditions
ConditionsYield
Stage #1: Boc-homoPhe-Leu-Phe-NHNH2 With hydrogenchloride; tert-butyl nitrate In 1,4-dioxane; N,N-dimethyl-formamide at -30℃; for 0.166667h; Inert atmosphere;
Stage #2: (2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one With N-ethyl-N,N-diisopropylamine at -30 - 20℃;
54%
C17H20N4O4

C17H20N4O4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

N-[5-methyl-1-(4-methyl-1-{(S)-4-methyl-1-[(R)-2-methyloxiran-2-yl]-1-oxopentan-2-ylamino}-1-oxopentan-2-yl)-2-oxo-1,2-dihydropyridin-3-yl]pyrazine-2-carboxamide

N-[5-methyl-1-(4-methyl-1-{(S)-4-methyl-1-[(R)-2-methyloxiran-2-yl]-1-oxopentan-2-ylamino}-1-oxopentan-2-yl)-2-oxo-1,2-dihydropyridin-3-yl]pyrazine-2-carboxamide

Conditions
ConditionsYield
With 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); N-ethyl-N,N-diisopropylamine In dichloromethane for 6h; Inert atmosphere;50%
C18H21N3O6

C18H21N3O6

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

(S)-1-(2-acetamidoacetyl)-N-((S)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-1-oxo-3-phenylpropan-2-yl)-4-oxopyrrolidine-2-carboxamide

(S)-1-(2-acetamidoacetyl)-N-((S)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-1-oxo-3-phenylpropan-2-yl)-4-oxopyrrolidine-2-carboxamide

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;49%
C17H21N3O5

C17H21N3O5

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

(S)-1-(2-acetamidoacetyl)-N-((S)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-1-oxo-3-phenylpropan-2-yl)azetidine-2-carboxamide

(S)-1-(2-acetamidoacetyl)-N-((S)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-1-oxo-3-phenylpropan-2-yl)azetidine-2-carboxamide

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;49%
C22H26N4O6

C22H26N4O6

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

5-methyl-N-(2-((S)-2-((S)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-1-oxo-4-phenylbutan-2-ylcarbamoyl)pyrrolidin-1-yl)-2-oxoethyl)isoxazole-3-carboxamide

5-methyl-N-(2-((S)-2-((S)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-1-oxo-4-phenylbutan-2-ylcarbamoyl)pyrrolidin-1-yl)-2-oxoethyl)isoxazole-3-carboxamide

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;48%
C18H22FN3O5

C18H22FN3O5

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

(S)-1-(2-acetamidoacetyl)-N-((S)-3-(4-fluorophenyl)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-1-oxopropan-2-yl)pyrrolidine-2-carboxamide

(S)-1-(2-acetamidoacetyl)-N-((S)-3-(4-fluorophenyl)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-1-oxopropan-2-yl)pyrrolidine-2-carboxamide

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;47%
C24H33N5O7

C24H33N5O7

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

N-(4-((S)-2-((S)-1-(2-acetamidoacetyl)pyrrolidine-2-carboxamido)-3-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-3-oxopropyl)phenyl)morpholine-4-carboxamide

N-(4-((S)-2-((S)-1-(2-acetamidoacetyl)pyrrolidine-2-carboxamido)-3-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-3-oxopropyl)phenyl)morpholine-4-carboxamide

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;46%
C22H25N3O5

C22H25N3O5

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

(S)-1-(2-acetamidoacetyl)-N-((S)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-3-(naphthalen-1-yl)-1-oxopropan-2-yl)pyrrolidine-2-carboxamide

(S)-1-(2-acetamidoacetyl)-N-((S)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-3-(naphthalen-1-yl)-1-oxopropan-2-yl)pyrrolidine-2-carboxamide

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;43%
C17H21N3O5

C17H21N3O5

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

5-methyl-N-[5-methyl-1-(4-methyl-1-{(S)-4-methyl-1-[(R)-2-methyloxiran-2-yl]-1-oxopentan-2-ylamino}-1-oxopentan-2-yl)-2-oxo-1,2-dihydropyridin-3-yl]isoxazole-3-carboxamide

5-methyl-N-[5-methyl-1-(4-methyl-1-{(S)-4-methyl-1-[(R)-2-methyloxiran-2-yl]-1-oxopentan-2-ylamino}-1-oxopentan-2-yl)-2-oxo-1,2-dihydropyridin-3-yl]isoxazole-3-carboxamide

Conditions
ConditionsYield
With 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); N-ethyl-N,N-diisopropylamine In dichloromethane for 6h; Inert atmosphere;41%
C20H27N3O5

C20H27N3O5

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

(S)-N-((S)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-1-oxo-3-phenylpropan-2-yl)-1-(2-morpholinoacetyl)pyrrolidine-2-carboxamide

(S)-N-((S)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-1-oxo-3-phenylpropan-2-yl)-1-(2-morpholinoacetyl)pyrrolidine-2-carboxamide

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;39%
C15H25N3O5

C15H25N3O5

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

(S)-1-(2-acetamidoacetyl)-N-((S)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-1-oxohexan-2-yl)pyrrolidine-2-carboxamide

(S)-1-(2-acetamidoacetyl)-N-((S)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-1-oxohexan-2-yl)pyrrolidine-2-carboxamide

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;38%
C18H20F3N3O5

C18H20F3N3O5

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

(S)-N-((S)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-1-oxo-3-phenylpropan-2-yl)-1-(2-(2,2,2-trifluoroacetamido)acetyl)pyrrolidine-2-carboxamide

(S)-N-((S)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-1-oxo-3-phenylpropan-2-yl)-1-(2-(2,2,2-trifluoroacetamido)acetyl)pyrrolidine-2-carboxamide

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;38%
C20H25N3O6

C20H25N3O6

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

(S)-N-((S)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-1-oxo-3-phenylpropan-2-yl)-1-(2-(3-oxomorpholino)acetyl)pyrrolidine-2-carboxamide

(S)-N-((S)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-1-oxo-3-phenylpropan-2-yl)-1-(2-(3-oxomorpholino)acetyl)pyrrolidine-2-carboxamide

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;38%
C28H37N3O6Si

C28H37N3O6Si

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

(S)-1-(2-acetamidoacetyl)-N-((S)-3-(tert-butyldiphenylsilyloxy)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-1-oxopropan-2-yl)pyrrolidine-2-carboxamide

(S)-1-(2-acetamidoacetyl)-N-((S)-3-(tert-butyldiphenylsilyloxy)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-1-oxopropan-2-yl)pyrrolidine-2-carboxamide

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;37%
C21H24N4O5S

C21H24N4O5S

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

2-methyl-N-(2-((S)-2-((S)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-1-oxo-3-phenylpropan-2-ylcarbamoyl)pyrrolidin-1-yl)-2-oxoethyl)thiazole-5-carboxamide

2-methyl-N-(2-((S)-2-((S)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-1-oxo-3-phenylpropan-2-ylcarbamoyl)pyrrolidin-1-yl)-2-oxoethyl)thiazole-5-carboxamide

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;37%
C18H21F2N3O5

C18H21F2N3O5

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

(S)-1-(2-acetamidoacetyl)-4,4-difluoro-N-((S)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-1-oxo-3-phenylpropan-2-yl)pyrrolidine-2-carboxamide

(S)-1-(2-acetamidoacetyl)-4,4-difluoro-N-((S)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-1-oxo-3-phenylpropan-2-yl)pyrrolidine-2-carboxamide

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;33%
C25H25N5O5

C25H25N5O5

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

N-(2-((S)-2-((S)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-3-(naphthalen-2-yl)-1-oxopropan-2-ylcarbamoyl)pyrrolidin-1-yl)-2-oxoethyl)pyrazine-2-carboxamide

N-(2-((S)-2-((S)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-3-(naphthalen-2-yl)-1-oxopropan-2-ylcarbamoyl)pyrrolidin-1-yl)-2-oxoethyl)pyrazine-2-carboxamide

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;33%
C20H27N3O5

C20H27N3O5

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

(S)-1-(2-acetamidoacetyl)-N-((S)-3-(4-ethylphenyl)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-1-oxopropan-2-yl)pyrrolidine-2-carboxamide

(S)-1-(2-acetamidoacetyl)-N-((S)-3-(4-ethylphenyl)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-1-oxopropan-2-yl)pyrrolidine-2-carboxamide

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;32%
C22H24N4O6

C22H24N4O6

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

6-hydroxy-N-(2-((S)-2-((S)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-1-oxo-3-phenylpropan-2-ylcarbamoyl)pyrrolidin-1-yl)-2-oxoethyl)picolinamide

6-hydroxy-N-(2-((S)-2-((S)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-1-oxo-3-phenylpropan-2-ylcarbamoyl)pyrrolidin-1-yl)-2-oxoethyl)picolinamide

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;32%
C20H24N2O5

C20H24N2O5

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

benzyl 5-methyl-1-(4-methyl-1-{(S)-4-methyl-1-[(R)-2-methyloxiran-2-yl]-1-oxopentan-2-ylamino}-1-oxopentan-2-yl)-2-oxo-1,2-dihydropyridin-3-ylcarbamate

benzyl 5-methyl-1-(4-methyl-1-{(S)-4-methyl-1-[(R)-2-methyloxiran-2-yl]-1-oxopentan-2-ylamino}-1-oxopentan-2-yl)-2-oxo-1,2-dihydropyridin-3-ylcarbamate

Conditions
ConditionsYield
With 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); N-ethyl-N,N-diisopropylamine In dichloromethane for 6h; Inert atmosphere;31%
C24H27N3O5

C24H27N3O5

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

(S)-1-(2-acetamidoacetyl)-N-((S)-3-(biphenyl-4-yl)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-1-oxopropan-2-yl)pyrrolidine-2-carboxamide

(S)-1-(2-acetamidoacetyl)-N-((S)-3-(biphenyl-4-yl)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-1-oxopropan-2-yl)pyrrolidine-2-carboxamide

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;31%
C20H21N3O5

C20H21N3O5

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one
247068-84-4

(2S)-2-amino-4-methyl-1-[(2R)-2-methyloxiran-2-yl]pentan-1-one

(S)-1-(6-hydroxypicolinoyl)-N-((S)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-1-oxo-3-phenylpropan-2-yl)pyrrolidine-2-carboxamide

(S)-1-(6-hydroxypicolinoyl)-N-((S)-1-((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-ylamino)-1-oxo-3-phenylpropan-2-yl)pyrrolidine-2-carboxamide

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;31%

247068-84-4Relevant articles and documents

Allenone-Mediated Racemization/Epimerization-Free Peptide Bond Formation and Its Application in Peptide Synthesis

Wang, Penghui,Wang, Xuewei,Wang, Zhengning,Zhao, Junfeng

supporting information, p. 10374 - 10381 (2021/07/26)

Allenone has been identified as a highly effective peptide coupling reagent for the first time. The peptide bond was formed with an α-carbonyl vinyl ester as the key intermediate, the formation and subsequent aminolysis of which proceed spontaneously in a racemization-/epimerization-free manner. The allenone coupling reagent not only is effective for the synthesis of simple amides and dipeptides but is also amenable to peptide fragment condensation and solid-phase peptide synthesis (SPPS). The robustness of the allenone-mediated peptide bond formation was showcased incisively by the synthesis of carfilzomib, which involved a rare racemization-/epimerization-free N to C peptide elongation strategy. Furthermore, the successful synthesis of the model difficult peptide ACP (65-74) on a solid support suggested that this method was compatible with SPPS. This method combines the advantages of conventional active esters and coupling reagents, while overcoming the disadvantages of both strategies. Thus, this allenone-mediated peptide bond formation strategy represents a disruptive innovation in peptide synthesis.

Covalent docking modelling-based discovery of tripeptidyl epoxyketone proteasome inhibitors composed of aliphatic-heterocycles

Dong, Xiao-Wu,Zhang, Jian-Kang,Xu, Lei,Che, Jin-Xin,Cheng, Gang,Hu, Xiao-Bei,Sheng, Li,Gao, An-Hui,Li, Jia,Liu, Tao,Hu, Yong-Zhou,Zhou, Yu-Bo

, p. 602 - 614 (2019/01/11)

The potential of specific proteasome inhibitors to act as anti-cancer agents has attracted intensive investigations. The proteasome can be covalently inhibited by epoxyketone derivatives via a two-step reaction. Several computational approaches have been developed to mimic the covalent binding event. Compound 1 composed of a six-membered heterocyclic ring was designed by using covalent docking. With a possible different binding mode from the clinical compound Carfilzomib, it occupied the S5 pocket of 20S proteasome and showed favorable inhibitory activity. Subsequently optimization and evaluation were taken place. Among these compounds, 11h demonstrated extraordinary in vitro inhibitory activity and selectivity, and good in vivo proteasome inhibitory activity, a favorable pharmacokinetic profile and xenograft tumor inhibition. The possible binding pattern of compound 11h against proteasome was further fully explored via calculations, providing a theoretical basis for finding potent proteasome inhibitors.

BETA-SUBSTITUTED BETA-AMINO ACIDS AND ANALOGS AS CHEMOTHERAPEUTIC AGENTS AND USES THEREOF

-

Paragraph 0569; 0885; 0908, (2017/02/28)

β-Substituted β-amino acids, β-substituted β-amino acid derivatives, and β-substituted β-amino acid analogs and (bio)isosteres and their use as chemotherapeutic agents are disclosed. The β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs and (bio)isosteres are selective LAT1/4F2hc substrates and exhibit rapid uptake and retention in tumors expressing the LAT1/4F2hc transporter. Methods of synthesizing the β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs and methods of using the compounds for treating cancer are also disclosed. The β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs exhibit selective uptake in tumor cells expressing the LAT1/4F2hc transporter and accumulate in cancerous cells when administered to a subject in vivo. The β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs and (bio)isosteres exhibit cytotoxicity toward several tumor types.

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