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68858-20-8

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68858-20-8 Usage

Chemical Properties

white to light yellow crystal powde

Uses

It is potentially useful for proteomics studies and solid phase peptide synthesis techniques. Fmoc-valine (in addition to the other amino acids) is commonly used to synthesize 4-thiazolidinones (e.g. (E)-5-(4-Ethylbenzylidene)-2-thioxothiazolidin-4-one [E925745]) and 4-metathiazanones as well.

General Description

The product number for this product was previously 04-12-1039.To obtain a certificate of analysis (CoA) of a lot that begins with the letter “A”, please select the option in the right hand menu “Request a COA for Lot#s starting with A”.

Check Digit Verification of cas no

The CAS Registry Mumber 68858-20-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,8,8,5 and 8 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 68858-20:
(7*6)+(6*8)+(5*8)+(4*5)+(3*8)+(2*2)+(1*0)=178
178 % 10 = 8
So 68858-20-8 is a valid CAS Registry Number.
InChI:InChI=1/C20H21NO4/c1-12(2)18(19(22)23)21-20(24)25-11-17-15-9-5-3-7-13(15)14-8-4-6-10-16(14)17/h3-10,12,17-18H,11H2,1-2H3,(H,21,24)(H,22,23)/p-1/t18-/m0/s1

68858-20-8 Well-known Company Product Price

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  • TCI America

  • (F0299)  N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-valine  >98.0%(HPLC)(T)

  • 68858-20-8

  • 5g

  • 230.00CNY

  • Detail
  • TCI America

  • (F0299)  N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-valine  >98.0%(HPLC)(T)

  • 68858-20-8

  • 25g

  • 790.00CNY

  • Detail
  • Alfa Aesar

  • (B21030)  N-Fmoc-L-valine, 98%   

  • 68858-20-8

  • 5g

  • 356.0CNY

  • Detail
  • Alfa Aesar

  • (B21030)  N-Fmoc-L-valine, 98%   

  • 68858-20-8

  • 25g

  • 895.0CNY

  • Detail
  • Aldrich

  • (47638)  Fmoc-Val-OH  ≥98.0% (HPLC)

  • 68858-20-8

  • 47638-50G-F

  • 563.94CNY

  • Detail
  • Aldrich

  • (47638)  Fmoc-Val-OH  ≥98.0% (HPLC)

  • 68858-20-8

  • 47638-250G-F

  • 2,130.57CNY

  • Detail

68858-20-8SDS

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 (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methylbutanoic acid

1.2 Other means of identification

Product number -
Other names FMOC-VAL-OH

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:68858-20-8 SDS

68858-20-8Synthetic route

L-valine
72-18-4

L-valine

(fluorenylmethoxy)carbonyl chloride
28920-43-6

(fluorenylmethoxy)carbonyl chloride

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

Conditions
ConditionsYield
With sodium carbonate In 1,4-dioxane at 0 - 20℃;96%
Stage #1: L-valine With sodium hydrogencarbonate In 1,4-dioxane; water
Stage #2: (fluorenylmethoxy)carbonyl chloride In 1,4-dioxane; water at 0 - 20℃;
70%
With pyridine; HOBT bound to the polystyrene-divinylbenzene copolymer resin 1.) DMF, H2O, 25 deg C, 2.) DMF, H2O, 25 deg C; Yield given. Multistep reaction;
L-valine
72-18-4

L-valine

3-(9-Fluorenylmethoxycarbonyl)-benzothiazoline-2-thione
100803-86-9

3-(9-Fluorenylmethoxycarbonyl)-benzothiazoline-2-thione

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane for 12h; Ambient temperature;91%
L-valine
72-18-4

L-valine

(9-fluorenyl)methyl pentafluorophenyl carbonate
88744-04-1

(9-fluorenyl)methyl pentafluorophenyl carbonate

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetone Ambient temperature;90%
L-valine
72-18-4

L-valine

9-fluorenylmethyl N-succinimidyl carbonate
102774-86-7

9-fluorenylmethyl N-succinimidyl carbonate

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

Conditions
ConditionsYield
With triethylamine In water; acetonitrile for 1h;89%
L-valine
72-18-4

L-valine

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide for 0.166667h; Ambient temperature;87%
With sodium hydrogencarbonate In water; acetone86%
Stage #1: L-valine With N-cyclohexyl-cyclohexanamine In acetone at 20℃;
Stage #2: N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide With sodium carbonate In water; acetonitrile at 0 - 20℃; pH=8;
Stage #3: With potassium hydrogensulfate In water; acetonitrile pH=2 - 3;
82%
With sodium hydrogencarbonate In water; N,N-dimethyl-formamide at 0 - 20℃; for 2h;
With sodium carbonate In 1,4-dioxane; water at 20℃; for 18h;
L-valine
72-18-4

L-valine

Carbonic acid 1,3-dioxo-1,3-dihydro-isoindol-2-yl ester 9H-fluoren-9-ylmethyl ester

Carbonic acid 1,3-dioxo-1,3-dihydro-isoindol-2-yl ester 9H-fluoren-9-ylmethyl ester

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃; for 2h;86%
L-valine
72-18-4

L-valine

Carbonic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl ester 9H-fluoren-9-ylmethyl ester
99503-04-5

Carbonic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl ester 9H-fluoren-9-ylmethyl ester

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

Conditions
ConditionsYield
With tertiary amine In 1,4-dioxane; water for 3h;85%
N-(9-fluorenylmethoxycarbonyl)valine 1,1-dimethylallyl ester
851713-90-1

N-(9-fluorenylmethoxycarbonyl)valine 1,1-dimethylallyl ester

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

Conditions
ConditionsYield
With 4-methyl-morpholine; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 25℃;82%
L-valine
72-18-4

L-valine

4-(9-fluorenylmethoxycarbonyloxy) phenyl dimethylsulfonium methylsulfate

4-(9-fluorenylmethoxycarbonyloxy) phenyl dimethylsulfonium methylsulfate

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

Conditions
ConditionsYield
With triethylamine In water Ambient temperature;75%
L-valine
72-18-4

L-valine

polymer-bound Fmoc-O-succinimide

polymer-bound Fmoc-O-succinimide

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃; for 24h;75%
N-Fmoc-L-valine phenacyl ester

N-Fmoc-L-valine phenacyl ester

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

Conditions
ConditionsYield
With magnesium; acetic acid In methanol; N,N-dimethyl-formamide at 20℃; for 75h;
9-Fluorenylmethanol
24324-17-2

9-Fluorenylmethanol

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 72 percent / pyridine / CH2Cl2 / 5 h / Ambient temperature
2: 86 percent / NaHCO3 / H2O; acetone
View Scheme
Multi-step reaction with 2 steps
1: pyridine / dichloromethane / 0 - 20 °C / Inert atmosphere
2: sodium carbonate / water; 1,4-dioxane / 0 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: pyridine / dichloromethane / 0 - 20 °C / Inert atmosphere
2: sodium carbonate / water; 1,4-dioxane / 1 h / 0 - 20 °C / Inert atmosphere
View Scheme
dicyclohexylamine salt of N-hydroxysuccinimide
82911-72-6

dicyclohexylamine salt of N-hydroxysuccinimide

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 90 percent / CHCl3
2: 86 percent / NaHCO3 / H2O; acetone
View Scheme
N-cyclohexyl-cyclohexanamine
101-83-7

N-cyclohexyl-cyclohexanamine

chromium oxide activated nickel catalyst

chromium oxide activated nickel catalyst

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 95 percent / acetone
2: 90 percent / CHCl3
3: 86 percent / NaHCO3 / H2O; acetone
View Scheme
N-hydroxy-5-norbornene-2,3-dicarboximide
21715-90-2

N-hydroxy-5-norbornene-2,3-dicarboximide

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) NaOH / 1.) MeOH; 2.) benzene, 10-15 deg C, 2 h
2: pyridine / 1.) room temp., 1 h; 2.) 35 deg C, 3 h
3: 85 percent / tertiary amine / H2O; dioxane / 3 h
View Scheme
Chlorameisensaeure-N-hydroxy-norborn-5-en-2,3-dicarboximidester
99502-89-3

Chlorameisensaeure-N-hydroxy-norborn-5-en-2,3-dicarboximidester

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / 1.) room temp., 1 h; 2.) 35 deg C, 3 h
2: 85 percent / tertiary amine / H2O; dioxane / 3 h
View Scheme
Fmoc-Val-OPfp
86060-87-9

Fmoc-Val-OPfp

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

Conditions
ConditionsYield
With benzotriazol-1-ol; 17O-water In tetrahydrofuran; water at 20℃; for 240h;
C38H50NO6PolSi

C38H50NO6PolSi

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

Conditions
ConditionsYield
With pyridine; pyridine hydrogenfluoride In tetrahydrofuran at 20℃; for 3h;
(fluorenylmethoxy)carbonyl chloride
28920-43-6

(fluorenylmethoxy)carbonyl chloride

L-valine hydrochloride
17498-50-9, 25616-14-2, 31320-20-4

L-valine hydrochloride

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 2h;
(fluorenylmethoxy)carbonyl chloride
28920-43-6

(fluorenylmethoxy)carbonyl chloride

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium carbonate / dichloromethane; water / 20.5 h / 0 - 20 °C
2: sodium carbonate / water; acetone / 4 h / 20 °C / pH 9 - 10
View Scheme
L-valine
72-18-4

L-valine

N-(((9H-fluoren-9-yl)methoxy)carbonyloxy)-2-amino-2-oxoacetimidoyl cyanide
1370440-28-0

N-(((9H-fluoren-9-yl)methoxy)carbonyloxy)-2-amino-2-oxoacetimidoyl cyanide

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

Conditions
ConditionsYield
With sodium carbonate In water; acetone at 20℃; for 4h; pH=9 - 10;
D,L-valine
516-06-3

D,L-valine

A

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

B

N-(9-fluorenylmethoxycarbonyl)-D-valine
84624-17-9

N-(9-fluorenylmethoxycarbonyl)-D-valine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium carbonate / water; 1,4-dioxane / Cooling with ice
1.2: 5 h / 20 °C
2.1: trifluoroacetic acid / isopropyl alcohol; hexane / 25 °C / Resolution of racemate
View Scheme
(fluorenylmethoxy)carbonyl chloride
28920-43-6

(fluorenylmethoxy)carbonyl chloride

A

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

B

N-(9-fluorenylmethoxycarbonyl)-D-valine
84624-17-9

N-(9-fluorenylmethoxycarbonyl)-D-valine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium carbonate / water; 1,4-dioxane / Cooling with ice
1.2: 5 h / 20 °C
2.1: trifluoroacetic acid / isopropyl alcohol; hexane / 25 °C / Resolution of racemate
View Scheme
Fmoc-valine
126727-02-4

Fmoc-valine

A

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

B

N-(9-fluorenylmethoxycarbonyl)-D-valine
84624-17-9

N-(9-fluorenylmethoxycarbonyl)-D-valine

Conditions
ConditionsYield
With trifluoroacetic acid In hexane; isopropyl alcohol at 25℃; Reagent/catalyst; Resolution of racemate;
With chiral column based on 3,5-dimethylphenylcarbamoylated β-cyclodextrin combining cinchona alkaloid immobilized on silica gel In methanol; formic acid; triethylamine; acetonitrile at 25℃; Resolution of racemate; enantioselective reaction;
Fmoc-Val-OBt
124007-51-8

Fmoc-Val-OBt

A

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

B

benzotriazol-1-ol
2592-95-2

benzotriazol-1-ol

Conditions
ConditionsYield
With water for 24h; Kinetics;
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

2,5-dioxopyrrolidin-1-yl-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valinate
130878-68-1

2,5-dioxopyrrolidin-1-yl-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valinate

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 9h;100%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; dichloromethane at 0 - 25℃;96%
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃;96%
Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

(S)-(9H-fluoren-9-yl)methyl 1-chloro-3-methyl-1-oxobutan-2-ylcarbamate
103321-53-5

(S)-(9H-fluoren-9-yl)methyl 1-chloro-3-methyl-1-oxobutan-2-ylcarbamate

Conditions
ConditionsYield
With thionyl chloride In dichloromethane at 55 - 60℃; for 1h; Inert atmosphere;100%
With thionyl chloride In dichloromethane at 50 - 55℃; for 1h; Inert atmosphere;100%
With thionyl chloride In dichloromethane for 24h; Ambient temperature;90%
Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

(9H-fluoren-9-yl)methyl (S)-(1-fluoro-3-methyl-1-oxobutan-2-yl)carbamate
130858-93-4

(9H-fluoren-9-yl)methyl (S)-(1-fluoro-3-methyl-1-oxobutan-2-yl)carbamate

Conditions
ConditionsYield
With pyridine; trifluoro-[1,3,5]triazine In dichloromethane at 20℃; for 15h;100%
With pyridine; trifluoro-[1,3,5]triazine In dichloromethane for 4h; Ambient temperature;85%
With pyridine; trifluoro-[1,3,5]triazine In dichloromethane for 2h;70.2%
Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

2,2-dimethyl-3-(N-methyl-N-phenylamino)-2H-azirine
75755-40-7

2,2-dimethyl-3-(N-methyl-N-phenylamino)-2H-azirine

(9H-fluoren-9-yl)methyl 1-{(2S)-2-methyl-1-[({1,1-dimethyl-2-[methyl(phenyl)amino]-2-oxoethyl}amino)carbonyl]propyl}carbamate
259217-20-4

(9H-fluoren-9-yl)methyl 1-{(2S)-2-methyl-1-[({1,1-dimethyl-2-[methyl(phenyl)amino]-2-oxoethyl}amino)carbonyl]propyl}carbamate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 72h; Condensation;100%
Leu-Cys(Trt)-Ala-Wang resin

Leu-Cys(Trt)-Ala-Wang resin

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

Val-Leu-Cys(Trt)-Ala-Wang resin

Val-Leu-Cys(Trt)-Ala-Wang resin

Conditions
ConditionsYield
Stage #1: Leu-Cys(Trt)-Ala-Wang resin; Fmoc-Val-OH With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 3h;
Stage #2: With piperidine In N,N-dimethyl-formamide at 20℃; for 0.25h;
100%
Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

monomethoxy-polyethylene glycol

monomethoxy-polyethylene glycol

N-(9-fluorenylmethoxycarbonyl)-L-valine terminated monomethoxy-polyethylene glycol

N-(9-fluorenylmethoxycarbonyl)-L-valine terminated monomethoxy-polyethylene glycol

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 20℃;100%
L-valinamide
4540-60-7

L-valinamide

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

Fmoc-Val-Val-NH2

Fmoc-Val-Val-NH2

Conditions
ConditionsYield
With 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 2h;100%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide Product distribution; Further Variations:; Reagents;
6-(tert-butoxycarbonylamino)hexanoic acid
6404-29-1

6-(tert-butoxycarbonylamino)hexanoic acid

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
35661-39-3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Boc-Ahx-Val-Ala-OH
1000018-75-6

Boc-Ahx-Val-Ala-OH

Conditions
ConditionsYield
Multistep reaction.;100%
2-(Trimethylsilyl)ethanol
2916-68-9

2-(Trimethylsilyl)ethanol

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

(S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methyl-butyric acid 2-trimethylsilanyl-ethyl ester
1089192-59-5

(S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methyl-butyric acid 2-trimethylsilanyl-ethyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane Cooling with ice;100%
C36H37N3O4S3

C36H37N3O4S3

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

C56H56N4O7S3

C56H56N4O7S3

Conditions
ConditionsYield
With dmap; 2,4,6-trichlorobenzoyl chloride In toluene100%
Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

C6H12NO2Pol

C6H12NO2Pol

Conditions
ConditionsYield
Stage #1: Fmoc-Val-OH With pyridine; 2,6-Dichlorobenzoyl chloride In 1-methyl-pyrrolidin-2-one hydroxymethyl Merrifield resin;
Stage #2: With piperidine In 1-methyl-pyrrolidin-2-one for 0.5h; hydroxymethyl Merrifield resin;
100%
Stage #1: Fmoc-Val-OH With pyridine; acetic anhydride; 2,6-Dichlorobenzoyl chloride In 1-methyl-pyrrolidin-2-one for 18h; Sasrin resin;
Stage #2: With acetic anhydride In 1-methyl-pyrrolidin-2-one at 45℃; for 3h; Sasrin resin;
Stage #3: With piperidine In 1-methyl-pyrrolidin-2-one for 1h; Sasrin resin;
100%
fmoc-Leu-Alko Resin

fmoc-Leu-Alko Resin

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

N-Fmoc L-Phe
35661-40-6

N-Fmoc L-Phe

C32H53N5O6

C32H53N5O6

Conditions
ConditionsYield
Stage #1: fmoc-Leu-Alko Resin With piperidine In N,N-dimethyl-formamide Wang resin;
Stage #2: With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 1.5h; Wang resin; Heating;
Stage #3: Fmoc-Val-OH; N-Fmoc L-Phe Further stages;
100%
fmoc-Leu-Alko Resin

fmoc-Leu-Alko Resin

N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

N-Fmoc L-Phe
35661-40-6

N-Fmoc L-Phe

C28H45N5O6
1613374-23-4

C28H45N5O6

Conditions
ConditionsYield
Stage #1: fmoc-Leu-Alko Resin With piperidine In N,N-dimethyl-formamide Wang resin;
Stage #2: With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 1.5h; Wang resin; Heating;
Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Val-OH; N-Fmoc L-Phe Further stages;
100%
fmoc-Leu-Alko Resin

fmoc-Leu-Alko Resin

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

N-Fmoc L-Phe
35661-40-6

N-Fmoc L-Phe

N-(9-fluorenylmethyloxycarbonyl)-4-aminobutyric acid
116821-47-7

N-(9-fluorenylmethyloxycarbonyl)-4-aminobutyric acid

C30H49N5O6
1613374-25-6

C30H49N5O6

Conditions
ConditionsYield
Stage #1: fmoc-Leu-Alko Resin With piperidine In N,N-dimethyl-formamide Wang resin;
Stage #2: With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 1.5h; Wang resin; Heating;
Stage #3: Fmoc-Val-OH; N-Fmoc L-Phe; N-(9-fluorenylmethyloxycarbonyl)-4-aminobutyric acid Further stages;
100%
N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

Fmoc-Leu-OH
35661-60-0

Fmoc-Leu-OH

N-Fmoc L-Phe
35661-40-6

N-Fmoc L-Phe

Fmoc-Tyr(tBu)-OH
71989-38-3

Fmoc-Tyr(tBu)-OH

Fmoc-Thr(tBu)-OH
71989-35-0

Fmoc-Thr(tBu)-OH

H2N-Thr(tBu)-Phe-Leu-Tyr(tBu)-Val-Gly-OH

H2N-Thr(tBu)-Phe-Leu-Tyr(tBu)-Val-Gly-OH

Conditions
ConditionsYield
Stage #1: Fmoc-Thr(tBu)-OH With N-ethyl-N,N-diisopropylamine In dichloromethane for 3h;
Stage #2: With piperidine In N,N-dimethyl-formamide for 0.1h;
Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Val-OH; Fmoc-Leu-OH; N-Fmoc L-Phe; Fmoc-Tyr(tBu)-OH Further stages;
100%
Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

C65H124N2O5

C65H124N2O5

C85H143N3O8

C85H143N3O8

Conditions
ConditionsYield
With benzotriazol-1-ol; diisopropyl-carbodiimide In dichloromethane at 20 - 40℃;100%
Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

C69H130N4O7

C69H130N4O7

C89H149N5O10

C89H149N5O10

Conditions
ConditionsYield
With benzotriazol-1-ol; diisopropyl-carbodiimide In dichloromethane at 20 - 40℃; for 2h;100%
Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

2-((1S,2S)-3-(allyloxy)-1,2-dimethoxypropyl)aniline
1421051-27-5

2-((1S,2S)-3-(allyloxy)-1,2-dimethoxypropyl)aniline

(9H-fluoren-9-yl)methyl (S)-1-(2-((1S,2S)-3-(allyloxy)-1,2-dimethoxypropyl)phenylamino)-3-methyl-1-oxobutan-2-ylcarbamate
1421051-33-3

(9H-fluoren-9-yl)methyl (S)-1-(2-((1S,2S)-3-(allyloxy)-1,2-dimethoxypropyl)phenylamino)-3-methyl-1-oxobutan-2-ylcarbamate

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃; for 3h;99.5%
Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

Phorbol 13,20-diacetate
41621-85-6

Phorbol 13,20-diacetate

C44H51NO11

C44H51NO11

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane99%
Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

3-(Dimethylamino)-2,2-dimethyl-2H-azirine

3-(Dimethylamino)-2,2-dimethyl-2H-azirine

Fmoc-Val-Aib-NMe2
128422-14-0

Fmoc-Val-Aib-NMe2

Conditions
ConditionsYield
In diethyl ether Ambient temperature;99%
Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

cyanomethylene triphenylphosphorane
16640-68-9

cyanomethylene triphenylphosphorane

C40H35N2O3P
1124196-12-8

C40H35N2O3P

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 20h; Inert atmosphere;99%
pregn-4-ene-3,20-dione cyclic 20-(ethylene acetal) 3-oxime

pregn-4-ene-3,20-dione cyclic 20-(ethylene acetal) 3-oxime

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

pregn-4-ene-3,20-dione cyclic 20-(ethylene acetal) 3-O-(N-Fmoc-L-valine)-E-oxime
1185296-45-0

pregn-4-ene-3,20-dione cyclic 20-(ethylene acetal) 3-O-(N-Fmoc-L-valine)-E-oxime

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane Inert atmosphere;99%
pregn-4-ene-3,20-dione cyclic 20-(ethylene acetal) 3-oxime
1185296-44-9

pregn-4-ene-3,20-dione cyclic 20-(ethylene acetal) 3-oxime

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

pregn-4-ene-3,20-dione cyclic 20-(ethylene acetal) 3-O-(N-Fmoc-L-valine)-Z-oxime
1185296-48-3

pregn-4-ene-3,20-dione cyclic 20-(ethylene acetal) 3-O-(N-Fmoc-L-valine)-Z-oxime

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane Inert atmosphere;99%
Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

tert-butyl hexa-4,5-dienoate
1598407-82-9

tert-butyl hexa-4,5-dienoate

(R)-tert-butyl 4-(((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-methylbutanoyl)oxy)hex-5-enoate
1598407-88-5

(R)-tert-butyl 4-(((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-methylbutanoyl)oxy)hex-5-enoate

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (S,S)-2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane In 1,2-dichloro-ethane at 10℃; for 48h; Schlenk technique; Inert atmosphere; diastereoselective reaction;99%
Fmoc-alanine-Wang-resin

Fmoc-alanine-Wang-resin

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

acetic anhydride
108-24-7

acetic anhydride

(2S,3R)-Fmoc-O-benzyl-threonine
117872-75-0

(2S,3R)-Fmoc-O-benzyl-threonine

N-acetyl-L-valyl-L-(OBn)threonyl-L-alanine

N-acetyl-L-valyl-L-(OBn)threonyl-L-alanine

Conditions
ConditionsYield
Stage #1: Fmoc-alanine-Wang-resin With piperidine In N,N-dimethyl-formamide at 75℃; for 0.05h; Fmoc-Ala-Wang-resin; Inert atmosphere; Microwave irradiation;
Stage #2: With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 75℃; for 0.05h; Fmoc-Ala-Wang-resin; Inert atmosphere; Microwave irradiation;
Stage #3: Fmoc-Val-OH; acetic anhydride; (2S,3R)-Fmoc-O-benzyl-threonine Further stages;
99%
Fmoc-Gly-Wang resin

Fmoc-Gly-Wang resin

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

acetic anhydride
108-24-7

acetic anhydride

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-isoleucine
71989-23-6

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-isoleucine

N-acetyl-L-isoleucyl-L-valylglycine

N-acetyl-L-isoleucyl-L-valylglycine

Conditions
ConditionsYield
Stage #1: Fmoc-Gly-Wang resin With piperidine In N,N-dimethyl-formamide at 75℃; for 0.05h; Fmoc-Ala-Wang-resin; Inert atmosphere; Microwave irradiation;
Stage #2: With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 75℃; for 0.05h; Fmoc-Ala-Wang-resin; Inert atmosphere; Microwave irradiation;
Stage #3: Fmoc-Val-OH; acetic anhydride; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-isoleucine Further stages;
99%
Fmoc-Gly-Wang resin

Fmoc-Gly-Wang resin

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

N-Fmoc L-Phe
35661-40-6

N-Fmoc L-Phe

acetic anhydride
108-24-7

acetic anhydride

N-acetyl-L-phenylalanyl-L-valylglycine

N-acetyl-L-phenylalanyl-L-valylglycine

Conditions
ConditionsYield
Stage #1: Fmoc-Gly-Wang resin With piperidine In N,N-dimethyl-formamide at 75℃; for 0.05h; Fmoc-Ala-Wang-resin; Inert atmosphere; Microwave irradiation;
Stage #2: With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 75℃; for 0.05h; Fmoc-Ala-Wang-resin; Inert atmosphere; Microwave irradiation;
Stage #3: Fmoc-Val-OH; N-Fmoc L-Phe; acetic anhydride Further stages;
99%
Fmoc-Gly-Wang resin

Fmoc-Gly-Wang resin

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

acetic anhydride
108-24-7

acetic anhydride

Fmoc-Phg-OH
102410-65-1

Fmoc-Phg-OH

N-acetyl-L-phenylglycyl-L-valylglycine

N-acetyl-L-phenylglycyl-L-valylglycine

Conditions
ConditionsYield
Stage #1: Fmoc-Gly-Wang resin With piperidine In N,N-dimethyl-formamide at 75℃; for 0.05h; Fmoc-Ala-Wang-resin; Inert atmosphere; Microwave irradiation;
Stage #2: With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 75℃; for 0.05h; Fmoc-Ala-Wang-resin; Inert atmosphere; Microwave irradiation;
Stage #3: Fmoc-Val-OH; acetic anhydride; Fmoc-Phg-OH Further stages;
99%
Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

(4-(hydroxymethyl)phenyl)diphenylphosphine oxide
5068-20-2

(4-(hydroxymethyl)phenyl)diphenylphosphine oxide

C39H36NO5P

C39H36NO5P

Conditions
ConditionsYield
Stage #1: Fmoc-Val-OH; (4-(hydroxymethyl)phenyl)diphenylphosphine oxide With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.166667h;
Stage #2: With dmap In dichloromethane at 20℃; for 2h;
99%
Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

(((R)-2'-(((S,E)-6-((tert-butoxycarbonyl)amino)-3-hydroxyhex-4-enamido)methyl)-4-methyl-4,5-dihydro-[2,4'-bithiazole]-4-carbonyl)oxy)fermium

(((R)-2'-(((S,E)-6-((tert-butoxycarbonyl)amino)-3-hydroxyhex-4-enamido)methyl)-4-methyl-4,5-dihydro-[2,4'-bithiazole]-4-carbonyl)oxy)fermium

(((R)-2'-((5S,8S)-8-((1E,3E)-3-((tert-butoxycarbonyl)iminio)prop-1-en-1-yl)-1-(9H-fluoren-9-yl)-5-isopropyl-3,6,10-trioxo-2,7-dioxa-4,11-diazadodecan-12-yl)-4-methyl-4,5-dihydro-[2,4'-bithiazole]-4-carbonyl)oxy)fermium

(((R)-2'-((5S,8S)-8-((1E,3E)-3-((tert-butoxycarbonyl)iminio)prop-1-en-1-yl)-1-(9H-fluoren-9-yl)-5-isopropyl-3,6,10-trioxo-2,7-dioxa-4,11-diazadodecan-12-yl)-4-methyl-4,5-dihydro-[2,4'-bithiazole]-4-carbonyl)oxy)fermium

Conditions
ConditionsYield
Stage #1: Fmoc-Val-OH With 2,4,6-trichlorobenzoyl chloride; triethylamine In tetrahydrofuran at 0℃; for 1h; Yamaguchi Lactonization; Inert atmosphere;
Stage #2: (((R)-2'-(((S,E)-6-((tert-butoxycarbonyl)amino)-3-hydroxyhex-4-enamido)methyl)-4-methyl-4,5-dihydro-[2,4'-bithiazole]-4-carbonyl)oxy)fermium With dmap In tetrahydrofuran at 0 - 25℃; for 0.5h; Yamaguchi Lactonization; Inert atmosphere;
99%

68858-20-8Relevant articles and documents

Self-assembly and anion-response of azobenzene-based L-valinamide derivative

Li, Kechang,Xue, Pengchong

, p. 206 - 212 (2018)

An azobenzene-based L-valinamide derivative was synthesized, and its gelation ability and self-assembly in organic solvents were investigated. Results suggested that it is an excellent gelator and formed organogels in many solvents, such as 3-pentanone, aniline, o-dichlorobenzene (ODCB), CH2Cl2, THF, ethanol, DMSO, and DMF. Its self-assembly in ODCB gel was studied. Transmission electron microscopic observation suggested that the gelator can self-assemble into one-dimensional nanofibers in the gel, and this phenomenon is driven by hydrogen bonding between amide units and π-π interaction between azobenzene moieties. With the increase in gelator concentration, the gel-to-sol phase transition temperature increased and the gelation time of the solvent shortened. Moreover, the gel exhibit anion response. A gel-to-sol phase transition was found after fluoride anion was added, exhibiting selective response to F?.

COMPOUNDS, COMPOSITIONS, METHODS, AND USES FOR TREATING CANCER AND IMMUNOLOGICAL DISORDERS

-

Paragraph 0546; 0551-0552, (2020/02/06)

The present disclosure provides novel polypeptide-therapeutic compound or hormone-therapeutic compound conjugates using cleavable or non-cleavable linkers, whereby the polypeptide or hormone serves to target specific cells using receptor expression on the targeted cell to bind the ligand (polypeptide or hormone) carrying the therapeutic compound unlike antibody drug conjugates. Upon binding, the ligand and the therapeutic compound (multiples of the therapeutic compound in some embodiments) enter the cell by receptor-mediated endocytosis, and release drugs conjugated to the ligand by linkers, to interact with intracellular components to enhance, restore, or block a signal transduction process. The ligands for the polypeptide-therapeutic compound or hormone-therapeutic compound conjugates include, but are not limited to: cytokines, growth factors and hormones among other proteins with corresponding cell surface specific receptors. The disorders targeted by such polypeptide-therapeutic compound or hormone-therapeutic compound conjugates include, but are not limited to: immunological disorders (e.g., allergy and autoimmune disorders) and cancer.

Unwanted hydrolysis or α/β-peptide bond formation: How long should the rate-limiting coupling step take?

Goldschmidt G?z, Viktória,Nagy, Adrienn,Farkas, Viktor,Keszei, Ern?,Perczel, András

, p. 30720 - 30728 (2019/10/28)

Nowadays, in Solid Phase Peptide Synthesis (SPPS), being either manual, automated, continuous flow or microwave-assisted, the reaction with various coupling reagents takes place via in situ active ester formation. In this study, the formation and stability of these key active esters were investigated with time-resolved 1H NMR by using the common PyBOP/DIEA and HOBt/DIC coupling reagents for both α- and β-amino acids. Parallel to the amide bond formation, the hydrolysis of the α/β-active esters, a side reaction that is a considerable efficacy limiting factor, was studied. Based on the chemical nature/constitution of the active esters, three amino acid categories were determined: (i) the rapidly hydrolyzing ones (t 24 h) in solution. The current insight into the kinetics of this key hydrolysis side reaction serves as a guide to optimize the coupling conditions of α- and β-amino acids, thereby saving time and minimizing the amounts of reagents and amino acids to be used-all key factors of more environmentally friendly chemistry.

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