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2304-96-3

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2304-96-3 Usage

Chemical Properties

white to light yellow crystal powde

Uses

Nα-Cbz-L-asparagine is an N-Cbz-protected form of L-Asparagine (A790005). L-Asparagine was first isolated by Robiquet and Vauquelin from asparagus juice (a high source of L-asparagine). L-Asparagine is often incorporated into proteins, and is a basis for some cancer therapies as certain cancerous cells require L-asparagine for growth.

Check Digit Verification of cas no

The CAS Registry Mumber 2304-96-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,3,0 and 4 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 2304-96:
(6*2)+(5*3)+(4*0)+(3*4)+(2*9)+(1*6)=63
63 % 10 = 3
So 2304-96-3 is a valid CAS Registry Number.
InChI:InChI=1/C12H14N2O5/c13-10(15)6-9(11(16)17)14-12(18)19-7-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H2,13,15)(H,14,18)(H,16,17)/t9-/m1/s1

2304-96-3 Well-known Company Product Price

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  • TCI America

  • (C0573)  Nα-Carbobenzoxy-L-asparagine  >99.0%(T)

  • 2304-96-3

  • 1g

  • 145.00CNY

  • Detail
  • TCI America

  • (C0573)  Nα-Carbobenzoxy-L-asparagine  >99.0%(T)

  • 2304-96-3

  • 10g

  • 335.00CNY

  • Detail
  • Alfa Aesar

  • (L08592)  N(alpha)-Benzyloxycarbonyl-L-asparagine, 98+%   

  • 2304-96-3

  • 5g

  • 184.0CNY

  • Detail
  • Alfa Aesar

  • (L08592)  N(alpha)-Benzyloxycarbonyl-L-asparagine, 98+%   

  • 2304-96-3

  • 25g

  • 675.0CNY

  • Detail
  • Aldrich

  • (C6404)  Z-Asn-OH  99%

  • 2304-96-3

  • C6404-10G-A

  • 492.57CNY

  • Detail

2304-96-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name (2S)-4-amino-4-oxo-2-(phenylmethoxycarbonylamino)butanoic acid

1.2 Other means of identification

Product number -
Other names N-Cbz-L-Asparagine

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:2304-96-3 SDS

2304-96-3Synthetic route

(S)-N-benzyloxycarbonylaspargine t-butyl ester
25456-85-3

(S)-N-benzyloxycarbonylaspargine t-butyl ester

N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

Conditions
ConditionsYield
With triethylsilane; trifluoroacetic acid In dichloromethane for 0.583333h; Ambient temperature;98%
L-asparagine
70-47-3

L-asparagine

dimethylsulfonium methyl sulfate

dimethylsulfonium methyl sulfate

N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

Conditions
ConditionsYield
With triethylamine In water Ambient temperature;95%
L-asparagine
70-47-3

L-asparagine

benzyl chloroformate
501-53-1

benzyl chloroformate

N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

Conditions
ConditionsYield
With sodium carbonate In water85%
With sodium carbonate In 1,4-dioxane; water at 20℃; Substitution;84%
With sodium carbonate In 1,4-dioxane at 0 - 20℃; Inert atmosphere;84%
(S)-2-Benzyloxycarbonylamino-succinamic acid 3-methyl-but-2-enyl ester

(S)-2-Benzyloxycarbonylamino-succinamic acid 3-methyl-but-2-enyl ester

N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃;83%
N-benzyloxycarbonyl-D,L-asparagine methyl ester
160348-01-6

N-benzyloxycarbonyl-D,L-asparagine methyl ester

A

N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

B

N-benzyloxycarbonyl-D-asparagine methyl ester
160348-02-7

N-benzyloxycarbonyl-D-asparagine methyl ester

Conditions
ConditionsYield
With sodium hydroxide; Alcalase 2.4L from Bacillus sp; sodium chloride In tetrahydrofuran; phosphate buffer for 16h; pH=6.5;A n/a
B 46%
With sodium hydroxide; Alcalase 2.4L from Bacillus sp; sodium chloride In tetrahydrofuran; phosphate buffer for 2.1h; pH=6.5;A 44%
B n/a
L-Phenylalanine amide
5241-58-7

L-Phenylalanine amide

C19H21N5O5*H(1+)

C19H21N5O5*H(1+)

A

C7H9N3O*H(1+)

C7H9N3O*H(1+)

B

N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

Conditions
ConditionsYield
With sodium chloride; calcium chloride; papain In N,N-dimethyl-formamide at 25℃; for 0.416667h; pH=8; aq. buffer; Enzymatic reaction;A n/a
B 30.2%
C 6.1%
L-asparagine
70-47-3

L-asparagine

N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

Conditions
ConditionsYield
With sodium hydrogencarbonate; benzyl chloroformate
Z-Asp(OBzl)-OH
3479-47-8

Z-Asp(OBzl)-OH

N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

Conditions
ConditionsYield
With ammonia
N-benzyloxy-carbonyl-DL-asparagine
29880-22-6

N-benzyloxy-carbonyl-DL-asparagine

N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

Conditions
ConditionsYield
With Cinchonin
Multi-step reaction with 2 steps
1: 91 percent / SOCl2 / 0.25 h / 0 °C
2: 44 percent / Alcalase 2.4L from Bacillus sp.; NaCl; NaOH / aq. phosphate buffer; tetrahydrofuran / 2.1 h / pH 6.5
View Scheme
N-(benzyloxycarbonyl)-L-aspartic acid 4-methyl ester
3160-47-2

N-(benzyloxycarbonyl)-L-aspartic acid 4-methyl ester

N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

Conditions
ConditionsYield
With ammonia
N-Benzyloxycarbonyl-L-asparaginsaeure-β-
20806-05-7

N-Benzyloxycarbonyl-L-asparaginsaeure-β-

N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

Conditions
ConditionsYield
With trifluoroacetic acid
N-benzyloxy-carbonyl-DL-asparagine
29880-22-6

N-benzyloxy-carbonyl-DL-asparagine

A

(R)-4-amino-2-(((benzyloxy)carbonyl)amino)-4-oxobutanoic acid
4474-86-6

(R)-4-amino-2-(((benzyloxy)carbonyl)amino)-4-oxobutanoic acid

B

N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

Conditions
ConditionsYield
resolved on CSP cellulose tris(3,5-dimethylphenylcarbamate) by chiral HPLC;
benzyl chloroformate
501-53-1

benzyl chloroformate

N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 90 percent / Et3N / acetonitrile / 2 h / 5 °C
2: 95 percent / Et3N / H2O / Ambient temperature
View Scheme
benzyl alcohol
100-51-6

benzyl alcohol

N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: toluene / anfangs unter Kuehlung
2: MgO; water / unter Kuehlung
View Scheme
di(phenylmethyl) (2S)-2-[(phenylmethoxy)carbonylamino]-butane-1,4-dioate
5241-60-1

di(phenylmethyl) (2S)-2-[(phenylmethoxy)carbonylamino]-butane-1,4-dioate

N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous dioxane; aqueous NaOH
2: liquid NH3
View Scheme
N-Cbz-L-Asp
1152-61-0

N-Cbz-L-Asp

N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: toluene
2: aqueous dioxane; aqueous NaOH
3: liquid NH3
View Scheme
benzyl chloroformate
501-53-1

benzyl chloroformate

aqueous alanine

aqueous alanine

N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. NaHCO3
2: liq. NH3
View Scheme
Z-Asp-OBn
4779-31-1

Z-Asp-OBn

N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (i) diethyl-prop-1-ynyl-amine, THF, (ii) aq. NaOH, dioxane
2: CF3CO2H
View Scheme
methanol
67-56-1

methanol

N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

N-(benzyloxycarbonyl)asparagine methyl ester
4668-37-5

N-(benzyloxycarbonyl)asparagine methyl ester

Conditions
ConditionsYield
With acetyl chloride at -15℃;99%
With acetyl chloride at -15℃; for 24h;98%
With thionyl chloride at 0℃; for 0.25h;97%
N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

(S)-2-oxo-imidazolidine-1,5-dicarboxylic acid 1-benzyl ester
59760-01-9, 76497-31-9, 46961-70-0

(S)-2-oxo-imidazolidine-1,5-dicarboxylic acid 1-benzyl ester

Conditions
ConditionsYield
With sodium hydroxide; bromine In water at 55℃; for 3h; Hofmann rearrangement;99%
With sodium hydroxide; bromine In water at 55℃; for 3h;92%
With hypobromous acid83%
L-phenylalanine tert-butyl ester
16874-17-2

L-phenylalanine tert-butyl ester

N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

2-(2-benzyloxycarbonylamino-3-carbamoylpropionylamino)-3-phenylpropionic acid tert-butyl ester
21467-13-0

2-(2-benzyloxycarbonylamino-3-carbamoylpropionylamino)-3-phenylpropionic acid tert-butyl ester

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 2h;98%
N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

glycine ethyl ester hydrochloride
5680-79-5

glycine ethyl ester hydrochloride

N2-(carboxybenzyl)-L-asparaginylglycine methyl ester
329257-17-2

N2-(carboxybenzyl)-L-asparaginylglycine methyl ester

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; Darkness;98%
N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

benzyl alcohol
100-51-6

benzyl alcohol

(S)-benzyl 2-(((benzyloxy)carbonyl)amino)-3-cyanopropanoate
82215-18-7

(S)-benzyl 2-(((benzyloxy)carbonyl)amino)-3-cyanopropanoate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;95%
N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

(S)-3-amino-2-(((benzyloxy)carbonyl)amino)propanoic acid
35761-26-3

(S)-3-amino-2-(((benzyloxy)carbonyl)amino)propanoic acid

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene In water; ethyl acetate; acetonitrile at 20℃; for 4h; Hoffmann rearrangement;93%
With [bis(acetoxy)iodo]benzene Hofmann rearrangement;92%
With [bis(acetoxy)iodo]benzene In water; ethyl acetate; acetonitrile Hoffmann degradation;92%
L-glutamine tert-butyl ester
41444-88-6

L-glutamine tert-butyl ester

N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

Z-Asn-Gln-OBut
65895-51-4

Z-Asn-Gln-OBut

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;93%
methanol
67-56-1

methanol

N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

benzyl N-(2-carbamoyl-1-methoxyethyl)carbamate

benzyl N-(2-carbamoyl-1-methoxyethyl)carbamate

Conditions
ConditionsYield
With 3-(1-piperidino)propyl-functionalized silica gel at 10℃; Hofer-Moest reaction; Electrolysis;93%
N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

N-(benzyloxycarbonyl)-3-cyano-L-alanine
3309-41-9

N-(benzyloxycarbonyl)-3-cyano-L-alanine

Conditions
ConditionsYield
With pyridine; trifluoroacetic anhydride In tetrahydrofuran at -10 - 20℃; for 15h;92%
With pyridine; p-toluenesulfonyl chloride
With pyridine; acetic anhydride
N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride
7524-50-7

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

benzyloxycarbonylasparaginyl-phenylalanine methyl ester
4976-86-7

benzyloxycarbonylasparaginyl-phenylalanine methyl ester

Conditions
ConditionsYield
With Sephadex G-50; triethylamine; bromelain In ethyl acetate at 37℃; for 7h;90%
(i) carbonochloridic acid adamantan-1-yl ester, Et3N, THF, dioxane, (ii) /BRN= 3597948/; Multistep reaction;
With diphenyl phosphoryl azide; triethylamine
L-Tyr-OMe
1080-06-4

L-Tyr-OMe

N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

Cbz-L-Asn-L-Tyr-OMe
20898-06-0

Cbz-L-Asn-L-Tyr-OMe

Conditions
ConditionsYield
With Sephadex G-50; triethylamine; bromelain In ethyl acetate at 37℃; for 7h;90%
With dicyclohexyl-carbodiimide
N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

H-Trp-Lys(Mtr)-Gly-OBut
84552-42-1

H-Trp-Lys(Mtr)-Gly-OBut

Z-Asn-Trp-Lys(Mtr)-Gly-OBut
84552-43-2

Z-Asn-Trp-Lys(Mtr)-Gly-OBut

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide; (3aR,4R,7S,7aS)-2-hydroxy-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione (N-hydroxy-5-exo-norbornene-2,3-dicarboximide) In N,N-dimethyl-formamide for 10h;87.4%
1-methyl-1-nitrosourea
684-93-5

1-methyl-1-nitrosourea

N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

N-(benzyloxycarbonyl)asparagine methyl ester
4668-37-5

N-(benzyloxycarbonyl)asparagine methyl ester

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; diethyl ether86.76%
N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

methyl (L)-leucinate hydrochloride
7517-19-3

methyl (L)-leucinate hydrochloride

N-Benzyloxycarbonyl-L-asparaginyl-L-leucine Methyl Ester
14317-83-0

N-Benzyloxycarbonyl-L-asparaginyl-L-leucine Methyl Ester

Conditions
ConditionsYield
With N-ethylmorpholine;; benzotriazol-1-ol In N,N-dimethyl-formamide 1) 2 h, -20 deg C, 2) 6 h, 0 deg C; overnight, r.t.;84%
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 0 - 25℃;50%
(i) 2-ethyl-5-(3-sulfo-phenyl)-isoxazolium betaine, (ii) /BRN= 3595133/; Multistep reaction;
(i) 2-ethyl-5-(4-sulfo-phenyl)-isoxazolium betaine, Et3N, MeNO2, (ii) /BRN= 3595133/, aq. NaOH; Multistep reaction;
N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

4,4'-Dimethoxybenzhydrol
728-87-0

4,4'-Dimethoxybenzhydrol

Nα-Cbz-Nγ-(4,4'-dimethoxybenzhydryl)-Asn-OH
28252-50-8

Nα-Cbz-Nγ-(4,4'-dimethoxybenzhydryl)-Asn-OH

Conditions
ConditionsYield
With sulfuric acid; acetic acid at 25℃; for 13.5h;84%
With sulfuric acid In acetic acid
N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

N-<(3S-amino)-2R-hydroxy-4-phenylbutyl>-N'-(1,1-dimethylethyl)-N-(2-methyl-propyl)urea
143224-64-0

N-<(3S-amino)-2R-hydroxy-4-phenylbutyl>-N'-(1,1-dimethylethyl)-N-(2-methyl-propyl)urea

[1S-[1R*(R*),2S*]]-N1[3-[[[(1,1-dimethylethyl)amino]carbonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-2-[(phenylmethylcarbamoyl)amino]butanediamide

[1S-[1R*(R*),2S*]]-N1[3-[[[(1,1-dimethylethyl)amino]carbonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-2-[(phenylmethylcarbamoyl)amino]butanediamide

Conditions
ConditionsYield
Stage #1: N-benzyloxycarbonyl-L-asparagine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In DMF (N,N-dimethyl-formamide) at 0℃; for 0.333333h;
Stage #2: N-<(3S-amino)-2R-hydroxy-4-phenylbutyl>-N'-(1,1-dimethylethyl)-N-(2-methyl-propyl)urea In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 7h;
Stage #3: With sodium hydrogencarbonate In DMF (N,N-dimethyl-formamide); water
83%
(Z)-2-(hydroxyimino)-2-phenylacetonitrile
7541-02-8

(Z)-2-(hydroxyimino)-2-phenylacetonitrile

N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

C20H18N4O5
126706-95-4

C20H18N4O5

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In ethyl acetate other solvent, 1. 0 deg C 1 h 2. rt 1 h;82%
With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran 1.) 10 min, -15 deg C 2.) 1 h, -15 deg C 3.) 1 h, rt;
N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

L-valine tert-butylester hydrochloride
13518-40-6

L-valine tert-butylester hydrochloride

N-(benzyloxycarbonyl)-L-asparaginyl-L-valine tert-butyl ester
26061-17-6

N-(benzyloxycarbonyl)-L-asparaginyl-L-valine tert-butyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane; d7-N,N-dimethylformamide at 0℃; for 3h;82%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 0℃; for 3h;81%
N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

(-)-(3S,4aS,8aS,2'R,3'R)-[3'-amino-2'-hydroxy-3'-(thiophen-2-yl)-propyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide
690223-68-8

(-)-(3S,4aS,8aS,2'R,3'R)-[3'-amino-2'-hydroxy-3'-(thiophen-2-yl)-propyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

(-)-(3S,4aS,8aS,2'R,3'R)-{1-[3-(3-tert-butyl-carbamoyl-decahydro-isoquinolin-2-yl)-2-hydroxy-1-thiophen-2-yl-propylcarbamoyl]-2-carbamoyl-ethyl}-carbamic acid bezyl ester

(-)-(3S,4aS,8aS,2'R,3'R)-{1-[3-(3-tert-butyl-carbamoyl-decahydro-isoquinolin-2-yl)-2-hydroxy-1-thiophen-2-yl-propylcarbamoyl]-2-carbamoyl-ethyl}-carbamic acid bezyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 6h;80%
N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

HCl*H-Ile-Leu-Aib-OMe

HCl*H-Ile-Leu-Aib-OMe

Z-Asn-Ile-Leu-Aib-OMe

Z-Asn-Ile-Leu-Aib-OMe

Conditions
ConditionsYield
With TEA; benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide for 34h; Ambient temperature;78%
N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

allyl bromide
106-95-6

allyl bromide

(S)-2-((benzyloxycarbonyl)amino)succinic acid 1-allyl ester 4-amide
848047-83-6

(S)-2-((benzyloxycarbonyl)amino)succinic acid 1-allyl ester 4-amide

Conditions
ConditionsYield
With sodium iodide In N,N-dimethyl-formamide for 24h;78%
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 48h;68%
With sodium iodide In N,N-dimethyl-formamide at 20℃; for 24h;57%
L-glutamine methyl ester
40846-98-8, 108258-30-6

L-glutamine methyl ester

N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

(S)-2-((S)-2-Benzyloxycarbonylamino-3-carbamoyl-propionylamino)-4-carbamoyl-butyric acid methyl ester
16305-90-1

(S)-2-((S)-2-Benzyloxycarbonylamino-3-carbamoyl-propionylamino)-4-carbamoyl-butyric acid methyl ester

Conditions
ConditionsYield
With 1-hydroxy-7-aza-benzotriazole; 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 0 - 20℃; for 10h;78%
N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

H-Gln-O-But
5132-46-7

H-Gln-O-But

Z-Asn-Gln-OBut
65895-51-4

Z-Asn-Gln-OBut

Conditions
ConditionsYield
With TEA; dicyclohexyl-carbodiimide; (3aR,4R,7S,7aS)-2-hydroxy-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione (N-hydroxy-5-exo-norbornene-2,3-dicarboximide) In N,N-dimethyl-formamide for 15h;77.8%
N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

benzyl bromide
100-39-0

benzyl bromide

benzyl Nα-benzyloxycarbonyl-L-asparaginate
4668-39-7

benzyl Nα-benzyloxycarbonyl-L-asparaginate

Conditions
ConditionsYield
Stage #1: N-benzyloxycarbonyl-L-asparagine With caesium carbonate In methanol; water pH=7;
Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 6h;
76%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;
N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

O-tert-butyl-L-serine tert-butyl ester hydrochloride
51537-21-4

O-tert-butyl-L-serine tert-butyl ester hydrochloride

N-carbobenzyloxy-L-asparaginyl-O-tert-butyl-L-serine tert-butyl ester
26055-00-5

N-carbobenzyloxy-L-asparaginyl-O-tert-butyl-L-serine tert-butyl ester

Conditions
ConditionsYield
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide75%
di-isopropyl ether
108-20-3

di-isopropyl ether

(4-methylphenyl)diphenylmethanol
5440-76-6

(4-methylphenyl)diphenylmethanol

N-benzyloxycarbonyl-L-asparagine
2304-96-3

N-benzyloxycarbonyl-L-asparagine

Z-Asn(Mtt)-OH

Z-Asn(Mtt)-OH

Conditions
ConditionsYield
With sulfuric acid; acetic anhydride; acetic acid In water; ethyl acetate75%

2304-96-3Relevant articles and documents

PYRROLOBENZODIAZEPINE DIMER PRECURSOR AND LIGAND-LINKER CONJUGATE COMPOUND THEREOF

-

Paragraph 0251; 0252, (2020/02/18)

The present invention relates to a pyrrolobenzodiazepine dimer prodrug and a ligand-linker conjugate compound thereof, a composition containing these, and therapeutic use thereof particularly as an anticancer drug. The stability of the compounds themselves and the stability thereof in plasma are excellent and the compounds are advantageous in terms of manifestation of toxicity, and thus the compounds are industrially useful in that it is possible to target proliferative diseases such as cancer, to perform a specific treatment, to maximize the drug efficacy, and to minimize the occurrence of side effects.

Phosphate bioisostere containing amphiphiles: A novel class of squaramide-based lipids

Saha, Abhishek,Panda, Subhankar,Paul, Saurav,Manna, Debasis

supporting information, p. 9438 - 9441 (2016/07/29)

We describe a novel class of amphiphiles with squaramide moiety as a phosphate bioisostere. Most synthesized squaramide-based amphiphiles have the favorable physicochemical properties of lipids, such as: formation of stable liposomes or giant unilamellar vesicles in aqueous solution, high phase-transition temperature, low vesicle leakage and phospholipase resistance properties.

Solution phase synthetic approach to fellutamide B

Yadav, Jhillu Singh,Dachavaram, Soma Shekar,Grée, René,Das, Saibal

supporting information, p. 3999 - 4001 (2015/06/08)

Abstract A convenient solution phase approach for the synthesis of fellutamide B with efficient purification techniques has been demonstrated on the molecule for the first time. The strategy involves the use of natural amino acids as starting materials and classical peptide coupling reactions. The synthesis has been achieved in 10 steps with overall yield of 26.7% making the synthesis facile.

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