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BOC-15-AMINO-4,7,10,13-TETRAOXAPENTADECANOIC ACID, also known as t-Boc-N-amido-PEG4-acid, is a PEGylated compound featuring a terminal carboxylic acid and a Boc-protected amino group. The hydrophilic PEG spacer enhances its solubility in aqueous environments, while the terminal carboxylic acid allows for the formation of stable amide bonds with primary amine groups through activation. The Boc group can be removed under mild acidic conditions to yield the free amine.

756525-91-4

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756525-91-4 Usage

Uses

Used in Pharmaceutical Industry:
BOC-15-AMINO-4,7,10,13-TETRAOXAPENTADECANOIC ACID is used as a substitution variant of cocaine esterase for improved stability. This application is crucial for the treatment of cocaine overdose, as it helps in the rapid metabolism and detoxification of the drug, reducing its harmful effects on the body.

Check Digit Verification of cas no

The CAS Registry Mumber 756525-91-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 7,5,6,5,2 and 5 respectively; the second part has 2 digits, 9 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 756525-91:
(8*7)+(7*5)+(6*6)+(5*5)+(4*2)+(3*5)+(2*9)+(1*1)=194
194 % 10 = 4
So 756525-91-4 is a valid CAS Registry Number.

756525-91-4 Well-known Company Product Price

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  • Aldrich

  • (30953)  15-(Boc-amino)-4,7,10,13-tetraoxapentadecanoicacid  purum, ≥97.0% (TLC)

  • 756525-91-4

  • 30953-100MG

  • 1,910.61CNY

  • Detail
  • Aldrich

  • (30953)  15-(Boc-amino)-4,7,10,13-tetraoxapentadecanoicacid  purum, ≥97.0% (TLC)

  • 756525-91-4

  • 30953-500MG

  • 7,733.70CNY

  • Detail

756525-91-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-[2-[2-[2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid

1.2 Other means of identification

Product number -
Other names 15-T-BUTYLOXYCARBONYLAMINO-4,7,10,13-TETRAOXA-PENTADECANOIC ACID

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:756525-91-4 SDS

756525-91-4Synthetic route

benzyl (E)-2,2-dimethyl-4-oxo-3,8,11,14,17-pentaoxa-5-azaicos-18-en-20-oate

benzyl (E)-2,2-dimethyl-4-oxo-3,8,11,14,17-pentaoxa-5-azaicos-18-en-20-oate

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
756525-91-4

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran under 760.051 Torr; for 24h;100%
3-[2-(2-{2-[2-(2-aminoethoxy)ethoxy]ethoxy}ethoxy)ethoxy]propanoic acid
663921-15-1

3-[2-(2-{2-[2-(2-aminoethoxy)ethoxy]ethoxy}ethoxy)ethoxy]propanoic acid

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
756525-91-4

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran; water at 20℃; Cooling with ice;93%
2-<2-<2-<2-<(tert-Butoxycarbonyl)amino>ethoxy>ethoxy>ethoxy>ethanol
106984-09-2

2-<2-<2-<2-<(tert-Butoxycarbonyl)amino>ethoxy>ethoxy>ethoxy>ethanol

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
756525-91-4

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 4-methyl-morpholine / dichloromethane / 18 h / 20 °C
2: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 24 h / 760.05 Torr
View Scheme
3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
756525-91-4

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid

C19H22ClN5*2C2HF3O2

C19H22ClN5*2C2HF3O2

C35H51ClN6O7

C35H51ClN6O7

Conditions
ConditionsYield
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 22℃; for 1.5h;100%
3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
756525-91-4

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid

C19H25N5S

C19H25N5S

C35H54N6O7S

C35H54N6O7S

Conditions
ConditionsYield
With 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 22℃; for 3h;100%
3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
756525-91-4

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid

C20H24ClN5*C2HF3O2

C20H24ClN5*C2HF3O2

C36H53ClN6O7

C36H53ClN6O7

Conditions
ConditionsYield
With 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 22℃; for 1h;100%
3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
756525-91-4

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid

(S)-4,11-diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl piperazine-1-carboxylate
97682-37-6

(S)-4,11-diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl piperazine-1-carboxylate

(S)-4,11-diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl 4-[3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoyl]piperazine-1-carboxylate

(S)-4,11-diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl 4-[3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoyl]piperazine-1-carboxylate

Conditions
ConditionsYield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 24h;99%
3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
756525-91-4

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid

rac-tyrosine benzyl ester p-toluenesulfonate

rac-tyrosine benzyl ester p-toluenesulfonate

t-boc-NH-dPEG4-CO-Tyr-OBn

t-boc-NH-dPEG4-CO-Tyr-OBn

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 5 - 20℃;98%
3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
756525-91-4

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid

4,11-diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl (S)-4-(aminomethyl)cyclohexanecarboxylate

4,11-diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl (S)-4-(aminomethyl)cyclohexanecarboxylate

(S)-4,11-diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl 4-(21,21-dimethyl-3,19-dioxo-6,9,12,15,20-pentaoxa-2,18-diazadocosyl)cyclohexanecarboxylate

(S)-4,11-diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl 4-(21,21-dimethyl-3,19-dioxo-6,9,12,15,20-pentaoxa-2,18-diazadocosyl)cyclohexanecarboxylate

Conditions
ConditionsYield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 24h;96%
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
756525-91-4

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid

2,5-dioxopyrrolidin-1-yl 2,2-dimethyl-4-oxo-3,8,11,14,17-pentaoxa-5-azaicosan-20-oate

2,5-dioxopyrrolidin-1-yl 2,2-dimethyl-4-oxo-3,8,11,14,17-pentaoxa-5-azaicosan-20-oate

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 18h;94%
With dicyclohexyl-carbodiimide In dichloromethane
With dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 2h;
With dicyclohexyl-carbodiimide In dichloromethane at 20℃;
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;
3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
756525-91-4

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid

(2S,4R)-1-[(2S)-2-azanyl-3,3-dimethylbutanoyl]-N-[[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl]-4-oxidanylpyrrolidine-2-carboxamide
1448297-52-6

(2S,4R)-1-[(2S)-2-azanyl-3,3-dimethylbutanoyl]-N-[[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl]-4-oxidanylpyrrolidine-2-carboxamide

tert-butyl ((S)-17-((2S,4R)-4-hydroxy-2-((4-(4-methylthiazol-5-yl)benzyl)carbamoyl)pyrrolidine-1-carbonyl)-18,18-dimethyl-15-oxo-3,6,9,12-tetraoxa-16-azanonadecyl)carbamate

tert-butyl ((S)-17-((2S,4R)-4-hydroxy-2-((4-(4-methylthiazol-5-yl)benzyl)carbamoyl)pyrrolidine-1-carbonyl)-18,18-dimethyl-15-oxo-3,6,9,12-tetraoxa-16-azanonadecyl)carbamate

Conditions
ConditionsYield
With N-[(dimethylamino)-1H-1,2,3-triazolo[4,5-b]pyridine-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide; triethylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;92%
3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
756525-91-4

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid

1-amino-3,6,9,12-tetraoxapentadecan-15-oic acid hydrochloride

1-amino-3,6,9,12-tetraoxapentadecan-15-oic acid hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane at 20℃; for 2h;90%
3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
756525-91-4

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid

Propargylamine

Propargylamine

tert-butyl(15-oxo-3,6,9,12-tetraoxa-16-azanonadeca-18-yne-1-yl)carbamate

tert-butyl(15-oxo-3,6,9,12-tetraoxa-16-azanonadeca-18-yne-1-yl)carbamate

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 3h;89%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;72%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 16h; Inert atmosphere;71%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 16h; Inert atmosphere;71%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 16h; Inert atmosphere;71%
3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
756525-91-4

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid

C20H23ClN4O

C20H23ClN4O

C36H52ClN5O8

C36H52ClN5O8

Conditions
ConditionsYield
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 22℃; for 18h;85%
3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
756525-91-4

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid

(3-(5H,6H-11,12-didehydrodibenzo[b,f]azocin-5-yl)-3-oxopropyl)amine
1255942-06-3

(3-(5H,6H-11,12-didehydrodibenzo[b,f]azocin-5-yl)-3-oxopropyl)amine

N-boc protected ADIBO-PEG4-amine
1255942-12-1

N-boc protected ADIBO-PEG4-amine

Conditions
ConditionsYield
Stage #1: 3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid With 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.25h;
Stage #2: N-(3-aminopropionyl)-5,6-dihydro-11,12-didehydrodibenzo[b,f]azocine In dichloromethane at 20℃; for 4h;
80%
Stage #1: 3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.25h;
Stage #2: N-(3-aminopropionyl)-5,6-dihydro-11,12-didehydrodibenzo[b,f]azocine In dichloromethane for 4h;
N-(tert-butyloxycarbonyl)-S-methylisothiourea
173998-77-1

N-(tert-butyloxycarbonyl)-S-methylisothiourea

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
756525-91-4

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid

N-tert-butoxycarbonyl-N’-[15-(tert-butoxycarbonylamino-4,7,10,13-tetraoxa)pentadecanoyl]-S-methylisothiourea
1334181-91-7

N-tert-butoxycarbonyl-N’-[15-(tert-butoxycarbonylamino-4,7,10,13-tetraoxa)pentadecanoyl]-S-methylisothiourea

Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;80%
With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In water; N,N-dimethyl-formamide at 20℃; for 16h;80%
3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
756525-91-4

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid

cholesterol
57-88-5

cholesterol

cholest-5-en-3-yl 2,2-dimethyl-4-oxo-3,8,11,14,17-pentaoxa-5-azaicosan-20-oate
1147885-57-1

cholest-5-en-3-yl 2,2-dimethyl-4-oxo-3,8,11,14,17-pentaoxa-5-azaicosan-20-oate

Conditions
ConditionsYield
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃;75%
3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
756525-91-4

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid

A

tert-butyl {trans-4-[(3-{5-[(2S)-1-methylpyrrolidin-2-yl]pyridin-3-yl}propyl)carbamoyl]cyclohexyl}carbamate
1351946-91-2

tert-butyl {trans-4-[(3-{5-[(2S)-1-methylpyrrolidin-2-yl]pyridin-3-yl}propyl)carbamoyl]cyclohexyl}carbamate

B

tert-butyl (19-{5-[(2S)-1-methylpyrrolidine-2-yl]pyridine-3-yl}-15-oxo-3,6,9,12-tetraoxa-16-azanonadeca1-yl)carbamate
1351946-92-3

tert-butyl (19-{5-[(2S)-1-methylpyrrolidine-2-yl]pyridine-3-yl}-15-oxo-3,6,9,12-tetraoxa-16-azanonadeca1-yl)carbamate

Conditions
ConditionsYield
A n/a
B 70%
3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
756525-91-4

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid

1-ammonio-15-oxo-3,6,9,12-tetraoxa-16-azaoctadecane-18-sulfonate

1-ammonio-15-oxo-3,6,9,12-tetraoxa-16-azaoctadecane-18-sulfonate

Conditions
ConditionsYield
Stage #1: 3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid With di(succinimido) carbonate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; Inert atmosphere;
Stage #2: Tau In tetrahydrofuran; water at 20℃;
70%
3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
756525-91-4

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid

benzyl bromide
100-39-0

benzyl bromide

C23H37NO8
1351397-20-0

C23H37NO8

Conditions
ConditionsYield
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 20℃; Cooling with ice;69%
3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
756525-91-4

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid

N-(5-aminopentyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazole-4-yl)pentanamide
115416-38-1

N-(5-aminopentyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazole-4-yl)pentanamide

C31H57N5O9S

C31H57N5O9S

Conditions
ConditionsYield
Stage #1: 3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 2.16667h;
Stage #2: N-(5-aminopentyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazole-4-yl)pentanamide With triethylamine In N,N-dimethyl-formamide at 20℃;
65%
3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
756525-91-4

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid

(2S,3S,4R)-3,4-bis-tert-butyldimethylsilyloxy-2-hexacosanoylamino-1-(2,3,4-tri-O-benzyl-6-hydroxy-α-D-galactopyranosyl)octadecane

(2S,3S,4R)-3,4-bis-tert-butyldimethylsilyloxy-2-hexacosanoylamino-1-(2,3,4-tri-O-benzyl-6-hydroxy-α-D-galactopyranosyl)octadecane

(2S,3S,4R)-3,4-bis-tert-butyldimethylsilyloxy-2-hexacosanoylamino-1-(2,3,4-tri-O-benzyl-6-carbonyl-1-ethyl-2-(tri-1-ethanoyl)1-ethanoyl-2-(tert-butoxy-carbonyl)amino)-α-D-galactopyranosyloctadecane

(2S,3S,4R)-3,4-bis-tert-butyldimethylsilyloxy-2-hexacosanoylamino-1-(2,3,4-tri-O-benzyl-6-carbonyl-1-ethyl-2-(tri-1-ethanoyl)1-ethanoyl-2-(tert-butoxy-carbonyl)amino)-α-D-galactopyranosyloctadecane

Conditions
ConditionsYield
Stage #1: 3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: (2S,3S,4R)-3,4-bis-tert-butyldimethylsilyloxy-2-hexacosanoylamino-1-(2,3,4-tri-O-benzyl-6-hydroxy-α-D-galactopyranosyl)octadecane In N,N-dimethyl-formamide for 5h;
63%
3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
756525-91-4

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid

A

tert-butyl (trans-4-{[2-({5-[(2S)-1-methylpyrrolidin-2-yl]pyridin-3-yl}oxy)ethyl]carbamoyl}cyclohexyl)carbamate
1351947-13-1

tert-butyl (trans-4-{[2-({5-[(2S)-1-methylpyrrolidin-2-yl]pyridin-3-yl}oxy)ethyl]carbamoyl}cyclohexyl)carbamate

B

tert-butyl [18-({5-[(2S)-1-methylpyrrolidine-2-yl]pyridine-3-yl}oxy)-15-oxo-3,6,9,12-tetraoxa-16-azaoctadeca-1-yl]carbamate
1351947-23-3

tert-butyl [18-({5-[(2S)-1-methylpyrrolidine-2-yl]pyridine-3-yl}oxy)-15-oxo-3,6,9,12-tetraoxa-16-azaoctadeca-1-yl]carbamate

Conditions
ConditionsYield
A n/a
B 56%
3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
756525-91-4

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid

(S)-1-(5-chloro-6-(2H-1,2,3-triazol-2-yl)pyridin-3-yl)-3-(2-chloro-7-(1-(methylamino)ethyl)pyrazolo[1,5-a]pyrimidin-6-yl)urea hydrochloride

(S)-1-(5-chloro-6-(2H-1,2,3-triazol-2-yl)pyridin-3-yl)-3-(2-chloro-7-(1-(methylamino)ethyl)pyrazolo[1,5-a]pyrimidin-6-yl)urea hydrochloride

tert-butyl (S)-(17-(2-chloro-6-(3-(5-chloro-6-(2H-1,2,3-triazol-2-yl)pyridin-3-yl)ureido)pyrazolo[1,5-a]pyrimidin-7-yl)-16-methyl-15-oxo-3,6,9,12-tetraoxa-16-azaoctadecyl)carbamate

tert-butyl (S)-(17-(2-chloro-6-(3-(5-chloro-6-(2H-1,2,3-triazol-2-yl)pyridin-3-yl)ureido)pyrazolo[1,5-a]pyrimidin-7-yl)-16-methyl-15-oxo-3,6,9,12-tetraoxa-16-azaoctadecyl)carbamate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide for 0.5h;56%
3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
756525-91-4

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid

2-(2-((6-chlorohexyl)oxy)ethoxy)ethan-1-aminium 2,2,2-trifluoroacetate
744203-61-0

2-(2-((6-chlorohexyl)oxy)ethoxy)ethan-1-aminium 2,2,2-trifluoroacetate

C26H51ClN2O9

C26H51ClN2O9

Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h;56%
3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
756525-91-4

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid

2-((5-chloro-2-((4-(piperazin-1-yl)phenyl)amino)pyrimidin-4-yl)amino)-N-methylbenzamide
1439934-41-4

2-((5-chloro-2-((4-(piperazin-1-yl)phenyl)amino)pyrimidin-4-yl)amino)-N-methylbenzamide

tert-butyl (15-(4-(4-((5-chloro-4-((2-(methylcarbamoyl)phenyl)amino)pyrimidin-2-yl)amino)phenyl)piperazin-1-yl)-15-oxo-3,6,9,12-tetraoxapentadecyl)carbamate

tert-butyl (15-(4-(4-((5-chloro-4-((2-(methylcarbamoyl)phenyl)amino)pyrimidin-2-yl)amino)phenyl)piperazin-1-yl)-15-oxo-3,6,9,12-tetraoxapentadecyl)carbamate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide for 3h;53.3%
3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
756525-91-4

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid

p-nitrobenzenesulfonamide
6325-93-5

p-nitrobenzenesulfonamide

C22H35N3O11S

C22H35N3O11S

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 5h; Inert atmosphere;53%
3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
756525-91-4

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid

rac-2-piperidin-4-yl-1,2,4,10-tetrahydro-3-oxa-10-azaphenanthren-9-one trifluoroacetate
1520890-12-3

rac-2-piperidin-4-yl-1,2,4,10-tetrahydro-3-oxa-10-azaphenanthren-9-one trifluoroacetate

rac-(2-{2-[2-(2-{3-oxo-3-[4-(9-oxo-1,4,9,10-tetrahydro-2H-3-oxa-10-azaphenanthren-2-yl)piperidin-1-yl]propoxy}ethoxy)ethoxy]ethoxy}ethyl)carbamic acid tert-butyl ester
1520890-16-7

rac-(2-{2-[2-(2-{3-oxo-3-[4-(9-oxo-1,4,9,10-tetrahydro-2H-3-oxa-10-azaphenanthren-2-yl)piperidin-1-yl]propoxy}ethoxy)ethoxy]ethoxy}ethyl)carbamic acid tert-butyl ester

Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 20℃; for 18h; Inert atmosphere;52%
3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
756525-91-4

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid

C44H70N12O13
1012050-70-2

C44H70N12O13

Conditions
ConditionsYield
Stage #1: 3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: RGD-C2 With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 6h;
46%
3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
756525-91-4

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid

(2S)-4-[[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]amino]-2-(tertbutoxycarbonylamino)-4-oxobutanoic acid

(2S)-4-[[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]amino]-2-(tertbutoxycarbonylamino)-4-oxobutanoic acid

3-[2-[2-[2-[2-[[(2S)-4-[[(2R,3R,4R,5S,6R)]-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]amino-2-(tert-butoxycarbonylamino)-4-oxobutanoyl]amino]ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid

3-[2-[2-[2-[2-[[(2S)-4-[[(2R,3R,4R,5S,6R)]-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]amino-2-(tert-butoxycarbonylamino)-4-oxobutanoyl]amino]ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid

Conditions
ConditionsYield
Stage #1: 3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid With hydrogenchloride In 1,4-dioxane at 20℃; for 1h;
Stage #2: (2S)-4-[[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]amino]-2-(tertbutoxycarbonylamino)-4-oxobutanoic acid 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 1,4-dioxane; N,N-dimethyl-formamide at 20℃; for 0.51h;
43%
3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
756525-91-4

3-[2-[2-[2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid

(E)-4-(4-(2-aminoethyl)piperazin-1-yl)-1-(4-(4-(4-phenoxyphenoxy)-5H-pyrrolo[3,2-d]pyrimidin-5-yl)piperidin-1-yl)but-2-en-1-one

(E)-4-(4-(2-aminoethyl)piperazin-1-yl)-1-(4-(4-(4-phenoxyphenoxy)-5H-pyrrolo[3,2-d]pyrimidin-5-yl)piperidin-1-yl)but-2-en-1-one

tert-butyl (E)-(15-oxo-18-(4-(4-oxo-4-(4-(4-(4-phenoxyphenoxy)-5H-pyrrolo[3,2-d]pyrimidin-5-yl)piperidin-1-yl)but-2-en-1-yl)piperazin-1-yl)-3,6,9,12-tetraoxa-16-azaoctadecyl)carbamate

tert-butyl (E)-(15-oxo-18-(4-(4-oxo-4-(4-(4-(4-phenoxyphenoxy)-5H-pyrrolo[3,2-d]pyrimidin-5-yl)piperidin-1-yl)but-2-en-1-yl)piperazin-1-yl)-3,6,9,12-tetraoxa-16-azaoctadecyl)carbamate

Conditions
ConditionsYield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In dichloromethane; ethyl acetate at 20℃; for 6h;33.4%

756525-91-4Relevant academic research and scientific papers

CONJUGATES OF A CELL-BINDING MOLECULE WITH CAMPTOTHECIN ANALOGS

-

Page/Page column 190-191, (2021/10/30)

Provided are conjugates of camptothecin analogs with a cell-binding molecule of formula (I), wherein R1, R2, R3, R4, R5, X, L, n, m, T and ----- are defined herein. It also provides methods of making the conjugates of camptothecin analogs to a cell-binding agent, as well as methods of using the conjugates in targeted treatment of cancer, infection, and immunological disorders.

A CONJUGATE OF A CYTOTOXIC AGENT TO A CELL BINDING MOLECULE WITH BRANCHED LINKERS

-

Page/Page column 221, (2021/01/23)

Provided is a conjugation of cytotoxic drug to a cell-binding molecule with a side-chain linker. It provides side-chain linkage methods of making a conjugate of a cytotoxic molecule to a cell-binding ligand, as well as methods of using the conjugate in targeted treatment of cancer, infection and immunological disorders.

Synthesis of carboxy-polyethylene glycol-amine (CA (PEG)n) and [1-14C]-CA (PEG)n via oxa-Michael addition of amino-polyethylene glycols to propiolates vs to acrylates

Song, Fengbin,Chen, Lu,Lin, Ronghui,Salter, Rhys

, p. 15 - 24 (2019/12/30)

Synthesis of carboxy-polyethylene glycol-amine (CA (PEG)n) via oxa-Michael addition of amino-polyethylene glycols to either acrylates or propiolates was investigated. Compared with the oxa-Michael addition to acrylates, the corresponding addition to propiolates was found to proceed under mild reaction conditions and afford the adducts in high yields from a broad scope of substrates. A two-step efficient and convenient synthesis of benzyl [1-14C]-propiolate from 14CO2 was therefore developed and utilized as a common synthon to afford practical and high yielding access to [1-14C]-CA (PEG)n.

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