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71989-28-1

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71989-28-1 Usage

Chemical Properties

white to light yellow crystal powde

Uses

N-Fmoc-L-methionine is an N-Fmoc-protected form of L-Methionine (M260440). L-Methionine is an essential amino acid that is obtained from our diet. L-Methionine can be found in grain legumes (such as lentils), and poultry. L-Methionine’s main function is to act as the primary “Start” sequence on mRNA so that the ribosomes can start translating the mRNA into proteins.

Check Digit Verification of cas no

The CAS Registry Mumber 71989-28-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,1,9,8 and 9 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 71989-28:
(7*7)+(6*1)+(5*9)+(4*8)+(3*9)+(2*2)+(1*8)=171
171 % 10 = 1
So 71989-28-1 is a valid CAS Registry Number.
InChI:InChI=1/C20H21NO4S/c1-26-11-10-18(19(22)23)21-20(24)25-12-17-15-8-4-2-6-13(15)14-7-3-5-9-16(14)17/h2-9,17-18H,10-12H2,1H3,(H,21,24)(H,22,23)/p-1/t18-/m0/s1

71989-28-1 Well-known Company Product Price

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  • TCI America

  • (F0296)  N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-methionine  >98.0%(HPLC)(T)

  • 71989-28-1

  • 1g

  • 115.00CNY

  • Detail
  • TCI America

  • (F0296)  N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-methionine  >98.0%(HPLC)(T)

  • 71989-28-1

  • 5g

  • 160.00CNY

  • Detail
  • TCI America

  • (F0296)  N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-methionine  >98.0%(HPLC)(T)

  • 71989-28-1

  • 25g

  • 590.00CNY

  • Detail
  • Alfa Aesar

  • (B21220)  N-Fmoc-L-methionine, 98+%   

  • 71989-28-1

  • 5g

  • 336.0CNY

  • Detail
  • Alfa Aesar

  • (B21220)  N-Fmoc-L-methionine, 98+%   

  • 71989-28-1

  • 25g

  • 1415.0CNY

  • Detail
  • Aldrich

  • (47634)  Fmoc-Met-OH  ≥98.0% (HPLC)

  • 71989-28-1

  • 47634-5G-F

  • 244.53CNY

  • Detail
  • Aldrich

  • (47634)  Fmoc-Met-OH  ≥98.0% (HPLC)

  • 71989-28-1

  • 47634-25G-F

  • 313.56CNY

  • Detail
  • Aldrich

  • (47634)  Fmoc-Met-OH  ≥98.0% (HPLC)

  • 71989-28-1

  • 47634-100G-F

  • 939.51CNY

  • Detail

71989-28-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name FMOC-L-Methionine

1.2 Other means of identification

Product number -
Other names Fmoc-methionine

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:71989-28-1 SDS

71989-28-1Synthetic route

2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methylsulfanyl-butyric acid methyl ester
500872-34-4

2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methylsulfanyl-butyric acid methyl ester

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

Conditions
ConditionsYield
With aluminium trichloride; N,N-dimethyl-aniline In dichloromethane98%
L-methionine
63-68-3

L-methionine

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

(9-fluorenyl)methyl pentafluorophenyl carbonate

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetone Ambient temperature;84%
L-methionine
63-68-3

L-methionine

1-[(9-fluorenylmethyloxycarbonyl)]benzotriazole
1131148-55-4

1-[(9-fluorenylmethyloxycarbonyl)]benzotriazole

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

Conditions
ConditionsYield
With triethylamine In water; acetonitrile at 20℃; for 2h;84%
L-methionine
63-68-3

L-methionine

4-(9-fluorenylmethoxycarbonyloxy) phenyl dimethylsulfonium methylsulfate

4-(9-fluorenylmethoxycarbonyloxy) phenyl dimethylsulfonium methylsulfate

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

Conditions
ConditionsYield
With triethylamine In water Ambient temperature;80%
L-methionine
63-68-3

L-methionine

(fluorenylmethoxy)carbonyl chloride
28920-43-6

(fluorenylmethoxy)carbonyl chloride

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

Conditions
ConditionsYield
Stage #1: L-methionine With chloro-trimethyl-silane In dichloromethane for 1h; Inert atmosphere; Reflux;
Stage #2: (fluorenylmethoxy)carbonyl chloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 5 - 20℃; for 1.5h;
80%
In acetonitrile at 20℃; for 0.25h; pH=9.2; aq. borate buffer;
Stage #1: L-methionine With sodium carbonate In 1,4-dioxane; water Cooling with ice;
Stage #2: (fluorenylmethoxy)carbonyl chloride In 1,4-dioxane; water at 20℃; for 5h;
L-methionine
63-68-3

L-methionine

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

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

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

Conditions
ConditionsYield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 50℃;78%
Stage #1: L-methionine 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;
61%
With sodium hydrogencarbonate In water; N,N-dimethyl-formamide at 0 - 20℃; for 2h;
C23H29NO4SSi

C23H29NO4SSi

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

Conditions
ConditionsYield
With methanol In dichloromethane for 0.5h; Ambient temperature; Yield given;
N-Fmoc-L-methionine phenacyl ester

N-Fmoc-L-methionine phenacyl ester

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

Conditions
ConditionsYield
With magnesium; acetic acid In methanol; N,N-dimethyl-formamide at 20℃; for 75h;
L-methionine
63-68-3

L-methionine

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: CH2Cl2 / 1 h / Heating
2: CH2Cl2 / 72 h / Ambient temperature
3: MeOH / CH2Cl2 / 0.5 h / Ambient temperature
View Scheme
O-(Trimethylsilyl)methionine
5269-64-7

O-(Trimethylsilyl)methionine

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: CH2Cl2 / 72 h / Ambient temperature
2: MeOH / CH2Cl2 / 0.5 h / Ambient temperature
View Scheme
(fluorenylmethoxy)carbonyl chloride
28920-43-6

(fluorenylmethoxy)carbonyl chloride

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 2 h / 10 °C
2: triethylamine / water; acetonitrile / 2 h / 20 °C
View Scheme
picolyl N-Fmoc-L-methioninate
1361400-97-6

picolyl N-Fmoc-L-methioninate

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

Conditions
ConditionsYield
With magnesium In methanol at 20℃; for 4h;
(fluorenylmethoxy)carbonyl chloride
28920-43-6

(fluorenylmethoxy)carbonyl chloride

A

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

B

Nα-fluorenyl-9-methoxycarbonyl-D-Met
71989-28-1, 144701-23-5, 112883-40-6

Nα-fluorenyl-9-methoxycarbonyl-D-Met

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
N-Fmoc-methionine
144701-23-5

N-Fmoc-methionine

A

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

B

Nα-fluorenyl-9-methoxycarbonyl-D-Met
71989-28-1, 144701-23-5, 112883-40-6

Nα-fluorenyl-9-methoxycarbonyl-D-Met

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℃; Reagent/catalyst; Resolution of racemate; enantioselective reaction;
DL-methionine
59-51-8

DL-methionine

A

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

B

Nα-fluorenyl-9-methoxycarbonyl-D-Met
71989-28-1, 144701-23-5, 112883-40-6

Nα-fluorenyl-9-methoxycarbonyl-D-Met

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
mono-oxidized L-methionine

mono-oxidized L-methionine

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

Conditions
ConditionsYield
Stage #1: mono-oxidized L-methionine With chloro-trimethyl-silane In N,N-dimethyl-formamide at 20℃; Pummerer Sulfoxide Rearrangement;
Stage #2: With 1,3-dihydro-imidazole-2-thione In N,N-dimethyl-formamide at 20℃; Solvent; Reagent/catalyst; Pummerer Sulfoxide Rearrangement;
90 %Chromat.
1,3-dihydro-imidazole-2-thione
872-35-5

1,3-dihydro-imidazole-2-thione

mono-oxidized L-methionine

mono-oxidized L-methionine

A

C23H23N3O4S2

C23H23N3O4S2

B

S-(((1H-imidazol-2-yl)thio)methyl)-N-(((9H-fluoren-9-yl)methoxy)carbonyl)-L-homocysteine

S-(((1H-imidazol-2-yl)thio)methyl)-N-(((9H-fluoren-9-yl)methoxy)carbonyl)-L-homocysteine

C

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

Conditions
ConditionsYield
Stage #1: mono-oxidized L-methionine With chloro-trimethyl-silane In ethyl acetate at 20℃; Pummerer Sulfoxide Rearrangement;
Stage #2: 1,3-dihydro-imidazole-2-thione In ethyl acetate at 20℃; Solvent; Reagent/catalyst; Pummerer Sulfoxide Rearrangement;
A n/a
B n/a
C 8 %Chromat.
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

(9H-fluoren-9-yl)methyl (S)-(1-amino-4-(methylthio)-1-oxobutan-2-yl)carbamate
314732-61-1

(9H-fluoren-9-yl)methyl (S)-(1-amino-4-(methylthio)-1-oxobutan-2-yl)carbamate

Conditions
ConditionsYield
Stage #1: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: With ammonium chloride In tetrahydrofuran; water at 0℃; for 0.5h;
100%
With pyridine; di-tert-butyl dicarbonate; ammonium bicarbonate In 1,4-dioxane; N,N-dimethyl-formamide at 20℃; for 48h; Inert atmosphere;91%
With ammonium bicarbonate; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In acetonitrile at 20℃; for 15h;86%
Fmoc-Leu-OH
35661-60-0

Fmoc-Leu-OH

Fmoc-Pro-OH
71989-31-6

Fmoc-Pro-OH

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

trifluoroacetic acid
76-05-1

trifluoroacetic acid

(4S)-4-{[(9-fluorenylmethyloxy)carbonyl]amino}-5-({2-[([(2-{[(9H-fluorenylmethoxy)carbonyl]amino}ethyl)amino]{[(4-methylphenyl)-sulfonyl]imino}methyl)amino]ethyl}amino)-5-oxopentanoic acid

(4S)-4-{[(9-fluorenylmethyloxy)carbonyl]amino}-5-({2-[([(2-{[(9H-fluorenylmethoxy)carbonyl]amino}ethyl)amino]{[(4-methylphenyl)-sulfonyl]imino}methyl)amino]ethyl}amino)-5-oxopentanoic acid

C49H83N13O10S3*C2HF3O2

C49H83N13O10S3*C2HF3O2

Conditions
ConditionsYield
Multistep reaction.;100%
C42H37ClNO6Pol

C42H37ClNO6Pol

C29H31NO5

C29H31NO5

N-Cbz-L-Phe
1161-13-3

N-Cbz-L-Phe

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

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

O-benzyl-N-Fmoc-L-serine
122889-11-6, 83792-48-7

O-benzyl-N-Fmoc-L-serine

Fmoc-Pro-OH
71989-31-6

Fmoc-Pro-OH

Fmoc-Ser(tBu)-OH
71989-33-8

Fmoc-Ser(tBu)-OH

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

Nα-FMOC-Nω-L-tosylarginine
139090-50-9, 83792-47-6

Nα-FMOC-Nω-L-tosylarginine

N-(((9H-fluoren-9-yl)methoxy)carbonyl)-O-(tert-butyldimethylsilyl)-L-threonine
146346-82-9

N-(((9H-fluoren-9-yl)methoxy)carbonyl)-O-(tert-butyldimethylsilyl)-L-threonine

N-alpha-(9-fluorenylmethyloxycarbonyl)-L-aspartic acid beta-allyl ester
146982-24-3

N-alpha-(9-fluorenylmethyloxycarbonyl)-L-aspartic acid beta-allyl ester

Z-Phe-Ala-Thr(TBS)-Met-Arg(Tos)-Tyr(Pen)-Pro-Ser(tBu)-Asp(OAll)-Ser(Bzl)-Asp(OtBu)-OH
1240360-55-7

Z-Phe-Ala-Thr(TBS)-Met-Arg(Tos)-Tyr(Pen)-Pro-Ser(tBu)-Asp(OAll)-Ser(Bzl)-Asp(OtBu)-OH

Conditions
ConditionsYield
Stage #1: C42H37ClNO6Pol With morpholine Automated synthesizer; solid phase reaction;
Stage #2: O-benzyl-N-Fmoc-L-serine With O‑(6‑chlorobezotriazol‑1‑yl)‑N,N,N,N‑tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; 6-chloro-1-hydroxybenzotriazole In 1-methyl-pyrrolidin-2-one Automated synthesizer; solid phase reaction;
Stage #3: C29H31NO5; N-Cbz-L-Phe; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; Fmoc-Pro-OH; Fmoc-Ser(tBu)-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine; Nα-FMOC-Nω-L-tosylarginine; N-(((9H-fluoren-9-yl)methoxy)carbonyl)-O-(tert-butyldimethylsilyl)-L-threonine; N-alpha-(9-fluorenylmethyloxycarbonyl)-L-aspartic acid beta-allyl ester Further stages;
100%
N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

N-Fmoc L-Phe
35661-40-6

N-Fmoc L-Phe

Fmoc-Glu(OtBu)-OH
71989-18-9

Fmoc-Glu(OtBu)-OH

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

N3-L-Gly-L-Phe-L-Glu(OtBu)-L-Met-L-Glu(OtBu)-L-Met-OH

N3-L-Gly-L-Phe-L-Glu(OtBu)-L-Met-L-Glu(OtBu)-L-Met-OH

Conditions
ConditionsYield
Stage #1: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine With N-ethyl-N,N-diisopropylamine In methanol; dichloromethane; N,N-dimethyl-formamide for 1.33333h; Inert atmosphere;
Stage #2: With piperidine In N,N-dimethyl-formamide for 0.333333h; Inert atmosphere;
Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; N-Fmoc L-Phe; Fmoc-Glu(OtBu)-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine Further stages;
99%
N-Fmoc L-Phe
35661-40-6

N-Fmoc L-Phe

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

Fmoc-L-Phe-L-Met-L-Phe-L-Met-OH

Fmoc-L-Phe-L-Met-L-Phe-L-Met-OH

Conditions
ConditionsYield
Stage #1: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine With N-ethyl-N,N-diisopropylamine In methanol; dichloromethane; N,N-dimethyl-formamide for 1.33333h; Inert atmosphere;
Stage #2: With piperidine In N,N-dimethyl-formamide for 0.333333h; Inert atmosphere;
Stage #3: N-Fmoc L-Phe; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine Further stages;
99%
Stage #1: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine With N-ethyl-N,N-diisopropylamine In dichloromethane for 1.08333h; Inert atmosphere;
Stage #2: With piperidine In N,N-dimethyl-formamide for 0.166667h; Inert atmosphere;
Stage #3: N-Fmoc L-Phe; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine Further stages;
99%
N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

N-Fmoc L-Phe
35661-40-6

N-Fmoc L-Phe

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

Nα-(9-fluorenylmethoxycarbonyl)-L-glutamic acid α-allyl ester
144120-54-7

Nα-(9-fluorenylmethoxycarbonyl)-L-glutamic acid α-allyl ester

cyclo-[L-Met-Gly-L-Met-L-Phe-L-Phe-L-Glu]

cyclo-[L-Met-Gly-L-Met-L-Phe-L-Phe-L-Glu]

Conditions
ConditionsYield
Stage #1: Nα-(9-fluorenylmethoxycarbonyl)-L-glutamic acid α-allyl ester With N-ethyl-N,N-diisopropylamine In dichloromethane for 0.916667h;
Stage #2: With piperidine In N,N-dimethyl-formamide for 0.333333h;
Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; N-Fmoc L-Phe; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine Further stages;
99%
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

1-methyl-1-phenylethyl 2,2,2-trichloroacetimidoate
147221-33-8

1-methyl-1-phenylethyl 2,2,2-trichloroacetimidoate

(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-methylsulfanyl-butyric acid 1-methyl-1-phenyl-ethyl ester

(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-methylsulfanyl-butyric acid 1-methyl-1-phenyl-ethyl ester

Conditions
ConditionsYield
In dichloromethane98%
In dichloromethane at 20℃; for 16h;95%
N-(2,2-diethoxyethyl)-3-methylbutan-1-amine
103647-81-0

N-(2,2-diethoxyethyl)-3-methylbutan-1-amine

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

(S)-(9H-fluoren-9-yl)methyl 1-((2,2-diethoxyethyl)(isopentyl)amino)-4-(methylthio)-1-oxobutan-2-ylcarbamate

(S)-(9H-fluoren-9-yl)methyl 1-((2,2-diethoxyethyl)(isopentyl)amino)-4-(methylthio)-1-oxobutan-2-ylcarbamate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 20℃; Cooling with ice;98%
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

3-hydroxy-3,4-dihydrobenzotriazine-4-one
28230-32-2

3-hydroxy-3,4-dihydrobenzotriazine-4-one

Fmoc-Met-ODhbt
119767-83-8

Fmoc-Met-ODhbt

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran at -15 - 4℃;95%
With thionyl chloride In dichloromethane Heating;92%
tert-Butyl 2,2,2-trichloroacetimidate
98946-18-0

tert-Butyl 2,2,2-trichloroacetimidate

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-methylsulfanyl-butyric acid tert-butyl ester

(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-methylsulfanyl-butyric acid tert-butyl ester

Conditions
ConditionsYield
In dichloromethane Heating;95%
(4-iodomethylphenoxy)acetic acid 2-oxo-2-phenylethyl ester
913987-81-2

(4-iodomethylphenoxy)acetic acid 2-oxo-2-phenylethyl ester

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

4-(Fmoc-methionyloxymethyl)phenoxyacetic acid 2-phenacyl ester
913987-86-7

4-(Fmoc-methionyloxymethyl)phenoxyacetic acid 2-phenacyl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine at 0℃;95%
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

L-methionine
63-68-3

L-methionine

Conditions
ConditionsYield
With sodium azide In N,N-dimethyl-formamide at 50℃; for 16h;95%
formaldehyd
50-00-0

formaldehyd

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

(4S)-3-(9-fluorenylmethyloxycarbonyl)-4-<2-(methylthio)ethyl>-5-oxooxazolidine
84000-02-2

(4S)-3-(9-fluorenylmethyloxycarbonyl)-4-<2-(methylthio)ethyl>-5-oxooxazolidine

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 2h; Reflux;94%
With toluene-4-sulfonic acid In toluene for 0.5h; Heating;88%
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

α-bromoacetophenone
70-11-1

α-bromoacetophenone

N-Fmoc-L-methionine phenacyl ester

N-Fmoc-L-methionine phenacyl ester

Conditions
ConditionsYield
With triethylamine In ethyl acetate; N,N-dimethyl-formamide at 0℃; for 18h;94%
(E)-1α,25-dihydroxy-2-(1′-amino-3′,6′,9′-trioxadodecan-12′-ylidene)-19-norvitamin D3

(E)-1α,25-dihydroxy-2-(1′-amino-3′,6′,9′-trioxadodecan-12′-ylidene)-19-norvitamin D3

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

(E)-1α,25-dihydroxy-2-[1′-(9′’H-fluoren-9′’-yl)-5′-[2′’’-(methylthio)ethyl]-3′,6′-dioxo-2′,10′,13′,16′-tetraoxa-4′,7′-diazanonadecan-19′-ylidene]-19-norvitamin D3

(E)-1α,25-dihydroxy-2-[1′-(9′’H-fluoren-9′’-yl)-5′-[2′’’-(methylthio)ethyl]-3′,6′-dioxo-2′,10′,13′,16′-tetraoxa-4′,7′-diazanonadecan-19′-ylidene]-19-norvitamin D3

Conditions
ConditionsYield
Stage #1: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 1h; Inert atmosphere;
Stage #2: (E)-1α,25-dihydroxy-2-(1′-amino-3′,6′,9′-trioxadodecan-12′-ylidene)-19-norvitamin D3 In dichloromethane Inert atmosphere;
94%
2,3,4,5,6-pentafluorophenol
771-61-9

2,3,4,5,6-pentafluorophenol

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

N-α-Fmoc-L-methionine pentafluorophenyl ester
86060-94-8

N-α-Fmoc-L-methionine pentafluorophenyl ester

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In ethyl acetate 0 deg C, 1 h; r.t., 1 h;93%
With dicyclohexyl-carbodiimide In ethyl acetate at 0℃; for 2h; Yield given;
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

pentafluorophenyl 4-nitrobenzenesulfonate
244633-31-6

pentafluorophenyl 4-nitrobenzenesulfonate

N-α-Fmoc-L-methionine pentafluorophenyl ester
86060-94-8

N-α-Fmoc-L-methionine pentafluorophenyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Esterification;93%
methyl 2-aminoisobutyrate hydrochloride
15028-41-8

methyl 2-aminoisobutyrate hydrochloride

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

Fmoc-L-Met-Aib-OMe
1124322-46-8

Fmoc-L-Met-Aib-OMe

Conditions
ConditionsYield
With 4-methyl-morpholine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;93%
2-docosyloxy-4-methoxybenzyl alcohol
1313025-22-7

2-docosyloxy-4-methoxybenzyl alcohol

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

C50H73NO6S
1313025-44-3

C50H73NO6S

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform at 20℃; for 1h; Cooling with ice;93%
L-leucine benzyl ester p-toluenesulfonate
1738-77-8

L-leucine benzyl ester p-toluenesulfonate

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

Fmoc-Met-Leu-OBzl ester

Fmoc-Met-Leu-OBzl ester

Conditions
ConditionsYield
Stage #1: L-leucine benzyl ester p-toluenesulfonate With triethylamine In dichloromethane at 20℃; for 0.5h;
Stage #2: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 20℃;
93%
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

(9H-fluoren-9-yl)methyl (S)-(1-fluoro-4-(methylthio)-1-oxobutan-2-yl)carbamate
130859-02-8

(9H-fluoren-9-yl)methyl (S)-(1-fluoro-4-(methylthio)-1-oxobutan-2-yl)carbamate

Conditions
ConditionsYield
With tetramethylammonium trifluoromethanethiolate In dichloromethane at 20℃; for 0.0833333h;92%
With pyridine; trifluoro-[1,3,5]triazine In dichloromethane for 4h; Ambient temperature;80%
With pyridine; trifluoro-[1,3,5]triazine In dichloromethane at 20℃;74%
With pyridine; trifluoro-[1,3,5]triazine In dichloromethane for 2h;72%
L-leucine benzyl ester hydrochloride
2462-35-3

L-leucine benzyl ester hydrochloride

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

Fmoc-Met-Leu-OBzl ester

Fmoc-Met-Leu-OBzl ester

Conditions
ConditionsYield
With C36H24B4N2O3 In toluene at 80℃; for 48h; Inert atmosphere; Molecular sieve;92%
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

(S)-2-((S)-2-Amino-4-methyl-pentanoylamino)-3-phenyl-propionic acid (benzhydryl-carbamoyl)-methyl ester; compound with trifluoro-acetic acid
119706-37-5

(S)-2-((S)-2-Amino-4-methyl-pentanoylamino)-3-phenyl-propionic acid (benzhydryl-carbamoyl)-methyl ester; compound with trifluoro-acetic acid

Fmoc-Met-Leu-Phe-OBg
119706-25-1

Fmoc-Met-Leu-Phe-OBg

Conditions
ConditionsYield
With 4-methyl-morpholine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In N,N-dimethyl-formamide for 0.5h; Ambient temperature;91%
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

Ala-Ile-Pro-O-t-Bu

Ala-Ile-Pro-O-t-Bu

N-Fmoc-Met-Ala-Ile-Pro-t-Bu

N-Fmoc-Met-Ala-Ile-Pro-t-Bu

Conditions
ConditionsYield
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Addition; Peptide-bond formation;91%
1,2,3-Benzotriazole
95-14-7

1,2,3-Benzotriazole

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

9H-fluoren-9-ylmethyl N-[(1S)-1-(1H-1,2,3-benzotriazol-1-ylcarbonyl)-3-(methylsulfanyl)propyl]carbamate
850232-62-1

9H-fluoren-9-ylmethyl N-[(1S)-1-(1H-1,2,3-benzotriazol-1-ylcarbonyl)-3-(methylsulfanyl)propyl]carbamate

Conditions
ConditionsYield
Stage #1: 1,2,3-Benzotriazole With thionyl chloride In tetrahydrofuran at 25℃; for 0.5h; Inert atmosphere;
Stage #2: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;
91%
Stage #1: 1,2,3-Benzotriazole With thionyl chloride In tetrahydrofuran at 35 - 40℃; for 0.333333h;
Stage #2: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine In tetrahydrofuran at 25℃; for 2h;
87%
Stage #1: 1,2,3-Benzotriazole With thionyl chloride In tetrahydrofuran at 40 - 50℃; for 0.333333h;
Stage #2: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine In tetrahydrofuran at 20℃; for 2h;
87%
With thionyl chloride In tetrahydrofuran at 20℃; for 2h;
curcumin
147556-16-9

curcumin

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

((1E,3Z,6E)-3-hydroxy-5-oxohepta-1,3,6-triene-1,7-diyl)bis(2-methoxy-4,1-phenylene) (2S,2'S)-bis(2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(methylthio)butanoate)

((1E,3Z,6E)-3-hydroxy-5-oxohepta-1,3,6-triene-1,7-diyl)bis(2-methoxy-4,1-phenylene) (2S,2'S)-bis(2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(methylthio)butanoate)

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -5 - 0℃;91%
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

Fmoc-methioninechloride
103321-54-6

Fmoc-methioninechloride

Conditions
ConditionsYield
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane for 1h; Ambient temperature;90.3%
With thionyl chloride In dichloromethane for 24h; Ambient temperature;90%
With pyridine; thionyl chloride In dichloromethane Heating;
N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

Fmoc-Met-N(CH3)-OCH3

Fmoc-Met-N(CH3)-OCH3

Conditions
ConditionsYield
Stage #1: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; 1,8-diazabicyclo[5.4.0]undec-7-ene In ethyl acetate; acetonitrile at 0℃; for 0.166667h;
Stage #2: N,O-dimethylhydroxylamine*hydrochloride With triethylamine In ethyl acetate; acetonitrile at 0℃; for 0.5h;
90%
Stage #1: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine With trichloroacetonitrile; triphenylphosphine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
Stage #2: N,O-dimethylhydroxylamine*hydrochloride With triethylamine In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;
78%
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine
Stage #1: N,O-dimethylhydroxylamine*hydrochloride; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In acetonitrile at 0℃; Inert atmosphere;
Stage #2: With N-ethyl-N,N-diisopropylamine In acetonitrile at 0 - 20℃; Inert atmosphere;
Fmoc-Leu-OH
35661-60-0

Fmoc-Leu-OH

N-Fmoc L-Phe
35661-40-6

N-Fmoc L-Phe

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine
71989-28-1

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

Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine

Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine

NH2-RMLRF-OH

NH2-RMLRF-OH

Conditions
ConditionsYield
Stage #1: N-Fmoc L-Phe With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.666667h;
Stage #2: With N-ethyl-N,N-diisopropylamine In methanol; dichloromethane at 20℃; for 0.166667h;
Stage #3: Fmoc-Leu-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine Further stages;
90%

71989-28-1Relevant articles and documents

Novel chiral stationary phases based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin combining cinchona alkaloid moiety

Zhu, Lunan,Zhu, Junchen,Sun, Xiaotong,Wu, Yaling,Wang, Huiying,Cheng, Lingping,Shen, Jiawei,Ke, Yanxiong

, p. 1080 - 1090 (2020/05/25)

Novel chiral selectors based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin connecting quinine (QN) or quinidine (QD) moiety were synthesized and immobilized on silica gel. Their chromatographic performances were investigated by comparing to the 3,5-dimethyl phenylcarbamoylated β-cyclodextrin (β-CD) chiral stationary phase (CSP) and 9-O-(tert-butylcarbamoyl)-QN-based CSP (QN-AX). Fmoc-protected amino acids, chiral drug cloprostenol (which has been successfully employed in veterinary medicine), and neutral chiral analytes were evaluated on CSPs, and the results showed that the novel CSPs characterized as both enantioseparation capabilities of CD-based CSP and QN/QD-based CSPs have broader application range than β-CD-based CSP or QN/QD-based CSPs. It was found that QN/QD moieties play a dominant role in the overall enantioseparation process of Fmoc-amino acids accompanied by the synergistic effect of β-CD moiety, which lead to the different enantioseparation of β-CD-QN-based CSP and β-CD-QD-based CSP. Furthermore, new CSPs retain extraordinary enantioseparation of cyclodextrin-based CSP for some neutral analytes on normal phase and even exhibit better enantioseparation than the corresponding β-CD-based CSP for certain samples.

Diethyl Selenodiglycolate: An Eco-Friendly Synthetic Antioxidant with Potential Application to Inflammatory Disorders

Archilha, Marcos V. L. R.,Giroldo, Lilian,Kuznetsov, Aleksey E.,Meotti, Flávia C.,Pinatto-Botelho, Marcos F.,da Silva, Railmara P.,dos Santos, Alcindo A.

, p. 1239 - 1248 (2020/10/14)

This study describes a single step, high yield and purity, ecofriendly and scalable procedure to prepare a selenium derivative (diethyl selenodiglycolate). Diethyl selenodiglycolate rapidly reduces hypochlorous acid (HOCl, second-order rate constant of 7 × 107 M?1 s?1) to generate its corresponding selenoxide. In activated HL-60 cells, diethyl selenodiglycolate selectively reacted with HOCl (half maximal inhibitory concentration (IC50) = 23.07 μM) but not with superoxide anion radical or hydrogen peroxide without any cytotoxicity. These results show that this synthetically simple selenide reacts in a very efficient and specific way with the harmful pro-oxidant HOCl being a promising compound to be applied in oxidative inflammatory-related conditions.

Preparation method of methionine derivative corrosion inhibitor

-

Paragraph 0019; 0020, (2016/10/31)

The invention discloses a preparation method of a methionine derivative corrosion inhibitor. The method comprises the following steps: synthesis of Fmoc-methionine: adding methionine and Fmoc-OSu into a DMF (N,N-dimethylformamide) solvent to react, and adding NaHCO3 to remove the solvent and residual amine compounds, thereby obtaining the product, wherein the yield is 78%; synthesis of Fmoc-methionine acyl chloride: adding the Fmoc-methionine into 25ml of CH2Cl2, and refluxing to react for 4 hours; and synthesis of Fmoc-methionine amide: after the acyl-chlorination reaction, directly adding into an equal mole of octadecylamine CH2Cl2 solution to obtain a yellow solid, and purifying the product by a chromatographic column separation process, wherein the eluting solution is composed of dichloromethane and methanol in a volume ratio of 20:1. According to the preparation method, the Fmoc- protective group is connected to the methionine molecule by amidation, and the adsorption site formed by the pi-electron-containing benzene ring enhances the adsorptivity of the corrosion inhibitor molecule. The hydrophobic long chain is connected to the methionine molecule to resist the attack of water molecules, so that a protective film is formed on the steel surface, thereby achieving the goal of corrosion inhibition.

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