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71989-38-3

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71989-38-3 Usage

Chemical Properties

white to light yellow crystal powde

Uses

Fmoc-Tyr(tBu)-OH Novabiochem?. CAS 71989-38-3, molar mass 459.55?g/mol.

General Description

Novabiochem?

Check Digit Verification of cas no

The CAS Registry Mumber 71989-38-3 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, 3 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 71989-38:
(7*7)+(6*1)+(5*9)+(4*8)+(3*9)+(2*3)+(1*8)=173
173 % 10 = 3
So 71989-38-3 is a valid CAS Registry Number.
InChI:InChI=1/C28H29NO5/c1-28(2,3)34-19-14-12-18(13-15-19)16-25(26(30)31)29-27(32)33-17-24-22-10-6-4-8-20(22)21-9-5-7-11-23(21)24/h4-15,24-25H,16-17H2,1-3H3,(H,29,32)(H,30,31)

71989-38-3 Well-known Company Product Price

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  • TCI America

  • (F0506)  Nα-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-tert-butyl-L-tyrosine  >98.0%(T)(HPLC)

  • 71989-38-3

  • 1g

  • 140.00CNY

  • Detail
  • TCI America

  • (F0506)  Nα-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-tert-butyl-L-tyrosine  >98.0%(T)(HPLC)

  • 71989-38-3

  • 5g

  • 480.00CNY

  • Detail
  • TCI America

  • (F0506)  Nα-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-tert-butyl-L-tyrosine  >98.0%(T)(HPLC)

  • 71989-38-3

  • 25g

  • 1,450.00CNY

  • Detail
  • Alfa Aesar

  • (H59730)  N-Fmoc-O-tert-butyl-L-tyrosine, 98%   

  • 71989-38-3

  • 5g

  • 617.0CNY

  • Detail
  • Alfa Aesar

  • (H59730)  N-Fmoc-O-tert-butyl-L-tyrosine, 98%   

  • 71989-38-3

  • 25g

  • 1466.0CNY

  • Detail
  • Aldrich

  • (47623)  Fmoc-Tyr(tBu)-OH  ≥98.0% (HPLC)

  • 71989-38-3

  • 47623-10G-F

  • 1,006.20CNY

  • Detail
  • Aldrich

  • (47623)  Fmoc-Tyr(tBu)-OH  ≥98.0% (HPLC)

  • 71989-38-3

  • 47623-25G-F

  • 1,987.83CNY

  • Detail
  • Aldrich

  • (47623)  Fmoc-Tyr(tBu)-OH  ≥98.0% (HPLC)

  • 71989-38-3

  • 47623-100G-F

  • 2,625.48CNY

  • Detail

71989-38-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Fmoc-O-tert-butyl-L-tyrosine

1.2 Other means of identification

Product number -
Other names (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]propanoic 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:71989-38-3 SDS

71989-38-3Synthetic route

Fmoc-Tyr(t-Bu)-1,1-dimethylallyl ester
851713-94-5

Fmoc-Tyr(t-Bu)-1,1-dimethylallyl ester

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

Fmoc-Tyr(tBu)-OH

Conditions
ConditionsYield
With 4-methyl-morpholine; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 25℃;91%
N-(9-Fluorenylmethoxycarbonyl)-O-tert-butyl-L-tyrosine Methyl Ester
132409-94-0

N-(9-Fluorenylmethoxycarbonyl)-O-tert-butyl-L-tyrosine Methyl Ester

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

Fmoc-Tyr(tBu)-OH

Conditions
ConditionsYield
With lithium iodide In ethyl acetate Reagent/catalyst; Reflux;84.3%
With sodium carbonate In acetonitrile for 15h;74%
Fmoc-Tyr(tBu)-OEt

Fmoc-Tyr(tBu)-OEt

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

Fmoc-Tyr(tBu)-OH

Conditions
ConditionsYield
With aluminum (III) chloride In ethyl acetate Reflux;78.6%
O-t-Butyl-L-tyrosine
4727-00-8, 18822-59-8

O-t-Butyl-L-tyrosine

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

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

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

Fmoc-Tyr(tBu)-OH

Conditions
ConditionsYield
Stage #1: O-t-Butyl-L-tyrosine 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;
58%
With sodium carbonate In 1,4-dioxane; water at 20℃; for 18h;
Fmoc-Tyr(but)-O-Pha
146346-74-9

Fmoc-Tyr(but)-O-Pha

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

Fmoc-Tyr(tBu)-OH

Conditions
ConditionsYield
With acetic acid; zinc Yield given;
With magnesium; acetic acid In methanol; N,N-dimethyl-formamide at 20℃; for 75h;
Fmoc-Tyr(tBu)-OH
71989-38-3

Fmoc-Tyr(tBu)-OH

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: diisopropylethylamine / ethyl acetate
2: 240 h
3: zinc, acetic acid
View Scheme
Fmoc-Tyr-O-Pha
146346-71-6

Fmoc-Tyr-O-Pha

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

Fmoc-Tyr(tBu)-OH

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 240 h
2: zinc, acetic acid
View Scheme
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

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

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

Fmoc-Tyr(tBu)-OH

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 97 percent / 10percent Na2CO3 / dioxane; H2O / 20 h / 0 deg C to r.t.
2: 83 percent / conc. H2SO4 / CH2Cl2 / 6 h / 258.6 Torr / Ambient temperature
3: 74 percent / aq. Na2CO3 / acetonitrile / 15 h
View Scheme
L-tyrosine methyl ester HCl
3417-91-2

L-tyrosine methyl ester HCl

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

Fmoc-Tyr(tBu)-OH

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 97 percent / 10percent Na2CO3 / dioxane; H2O / 20 h / 0 deg C to r.t.
2: 83 percent / conc. H2SO4 / CH2Cl2 / 6 h / 258.6 Torr / Ambient temperature
3: 74 percent / aq. Na2CO3 / acetonitrile / 15 h
View Scheme
Multi-step reaction with 4 steps
1: sodium carbonate / ethyl acetate; water / pH 8
2: sulfuric acid / dichloromethane / 120 h / 20 °C
3: palladium on activated charcoal; hydrogen / 25 °C
4: sodium carbonate / water; tetrahydrofuran / pH 9
View Scheme
Multi-step reaction with 3 steps
1: sodium carbonate / acetone; water / 8 h / 20 °C / pH 8 - 9
2: perchloric acid / 1 h / 20 °C / Cooling with ice
3: lithium iodide / ethyl acetate / Reflux
View Scheme
N-(fluorenyl-9-methoxycarbonyl)-L-tyrosine methyl ester
82911-79-3

N-(fluorenyl-9-methoxycarbonyl)-L-tyrosine methyl ester

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

Fmoc-Tyr(tBu)-OH

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 83 percent / conc. H2SO4 / CH2Cl2 / 6 h / 258.6 Torr / Ambient temperature
2: 74 percent / aq. Na2CO3 / acetonitrile / 15 h
View Scheme
Multi-step reaction with 2 steps
1: perchloric acid / 1 h / 20 °C / Cooling with ice
2: lithium iodide / ethyl acetate / Reflux
View Scheme
C42H40NO6Pol

C42H40NO6Pol

A

N-Fmoc-Tyr-OH
112883-29-1, 92954-90-0

N-Fmoc-Tyr-OH

B

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

Fmoc-Tyr(tBu)-OH

Conditions
ConditionsYield
With water; trifluoroacetic acid for 3h; Polystyrene crosslinked with divinylbenzene; Product distribution / selectivity;
C2H2O4*C13H26N2O4

C2H2O4*C13H26N2O4

C34H36N2O4S
1019691-75-8

C34H36N2O4S

A

Fmoc-Tyr(tBu)-Ala-Leu-OtBu
1019691-23-6

Fmoc-Tyr(tBu)-Ala-Leu-OtBu

B

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

Fmoc-Tyr(tBu)-OH

Conditions
ConditionsYield
Stage #1: C34H36N2O4S With Oxone In water; N,N-dimethyl-formamide at 25℃;
Stage #2: C2H2O4*C13H26N2O4 In N,N-dimethyl-formamide at 40℃; Further stages.;
(fluorenylmethoxy)carbonyl chloride
28920-43-6

(fluorenylmethoxy)carbonyl chloride

C13H19NO3*ClH

C13H19NO3*ClH

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

Fmoc-Tyr(tBu)-OH

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

(fluorenylmethoxy)carbonyl chloride

O-t-Butyl-L-tyrosine
4727-00-8, 18822-59-8

O-t-Butyl-L-tyrosine

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

Fmoc-Tyr(tBu)-OH

Conditions
ConditionsYield
With sodium carbonate In tetrahydrofuran; water pH=9;450 g
L-tyrosine
60-18-4

L-tyrosine

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

Fmoc-Tyr(tBu)-OH

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: thionyl chloride / Reflux
2: sodium carbonate / ethyl acetate; water / pH 8
3: sulfuric acid / dichloromethane / 120 h / 20 °C
4: palladium on activated charcoal; hydrogen / 25 °C
5: sodium carbonate / water; tetrahydrofuran / pH 9
View Scheme
Multi-step reaction with 4 steps
1: thionyl chloride / Reflux
2: sodium carbonate / acetone; water / 8 h / 20 °C / pH 8 - 9
3: perchloric acid / 1 h / 20 °C / Cooling with ice
4: lithium iodide / ethyl acetate / Reflux
View Scheme
Multi-step reaction with 4 steps
1: thionyl chloride / Reflux
2: sodium carbonate / acetone; water / 8 h / 20 °C / pH 8 - 9
3: perchloric acid / 1 h / Cooling with ice
4: aluminum (III) chloride / ethyl acetate / Reflux
View Scheme
N-(benzyloxycarbonyl)-L-tyrosine methyl ester
13512-31-7

N-(benzyloxycarbonyl)-L-tyrosine methyl ester

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

Fmoc-Tyr(tBu)-OH

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sulfuric acid / dichloromethane / 120 h / 20 °C
2: palladium on activated charcoal; hydrogen / 25 °C
3: sodium carbonate / water; tetrahydrofuran / pH 9
View Scheme
(S)-tert-butyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate
133852-23-0

(S)-tert-butyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate

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

Fmoc-Tyr(tBu)-OH

Conditions
ConditionsYield
With water Flow reactor;
L-tyrosine ethyl ester monohydrochloride
4089-07-0

L-tyrosine ethyl ester monohydrochloride

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

Fmoc-Tyr(tBu)-OH

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium carbonate / acetone; water / 8 h / 20 °C / pH 8 - 9
2: perchloric acid / 1 h / Cooling with ice
3: aluminum (III) chloride / ethyl acetate / Reflux
View Scheme
1-Adamantanamine
768-94-5

1-Adamantanamine

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

Fmoc-Tyr(tBu)-OH

(2S)-N-Adamantyl-3-[(4-tert-butoxy)phenyl]-2-(9-fluorenylmethoxycarbonylamino)propanamide
194673-21-7

(2S)-N-Adamantyl-3-[(4-tert-butoxy)phenyl]-2-(9-fluorenylmethoxycarbonylamino)propanamide

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide for 12h; Ambient temperature;100%
Fmoc-Tyr(tBu)-OH
71989-38-3

Fmoc-Tyr(tBu)-OH

allyl bromide
106-95-6

allyl bromide

allyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-tert-butoxyphenyl)propanoate
208655-83-8

allyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-tert-butoxyphenyl)propanoate

Conditions
ConditionsYield
Stage #1: Fmoc-Tyr(tBu)-OH With silver carbonate In N,N-dimethyl-formamide at 20℃; for 0.25h;
Stage #2: allyl bromide In N,N-dimethyl-formamide at 20℃; for 2.5h;
100%
Stage #1: Fmoc-Tyr(tBu)-OH With caesium carbonate In methanol at 20℃; for 2h; Metallation;
Stage #2: allyl bromide In N,N-dimethyl-formamide at 20℃; for 18h; Esterification; Further stages.;
98%
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 24h;97%
C153H228N16O19S
1258442-48-6

C153H228N16O19S

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

Fmoc-Tyr(tBu)-OH

C181H255N17O23S
1258442-40-8

C181H255N17O23S

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;100%
Fmoc-Tyr(tBu)-OH
71989-38-3

Fmoc-Tyr(tBu)-OH

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃; for 2h;100%
With trifluoroacetic acid In water at 20℃; for 2h;91.1%
With hydrogenchloride In water at 20℃; for 4h; Reagent/catalyst; Temperature; Time;
N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

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

C29H37N7O6
1454659-74-5

C29H37N7O6

Conditions
ConditionsYield
Stage #1: Fmoc-Leu-OH With pyridine; 2,6-dichlorobenzaldehyde In N,N-dimethyl-formamide
Stage #2: With pyridine; benzoyl chloride In N,N-dimethyl-formamide
Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; N-Fmoc L-Phe; Fmoc-Tyr(tBu)-OH 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-Tyr(tBu)-OH
71989-38-3

Fmoc-Tyr(tBu)-OH

(3,4,5-trioctadecyloxyphenyl)methan-1-ol
233281-31-7

(3,4,5-trioctadecyloxyphenyl)methan-1-ol

Fmoc-Try(tBu)-OKa

Fmoc-Try(tBu)-OKa

Conditions
ConditionsYield
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; for 0.583333h;100%
2,4-bis(docosyloxy)benzyl alcohol
931120-51-3

2,4-bis(docosyloxy)benzyl alcohol

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

Fmoc-Tyr(tBu)-OH

Fmoc-Tyr(tBu)-OKb, Kb=2,4-didocosyloxybenzyl

Fmoc-Tyr(tBu)-OKb, Kb=2,4-didocosyloxybenzyl

Conditions
ConditionsYield
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; for 0.5h;100%
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; for 0.5h;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

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

Fmoc-Tyr(tBu)-OH

(S)-3-cyclohexyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propionic acid
135673-97-1

(S)-3-cyclohexyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propionic acid

C31H41N5O7

C31H41N5O7

Conditions
ConditionsYield
Stage #1: (S)-3-cyclohexyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propionic acid With 4-methyl-morpholine; pyridine; 2,6-Dichlorobenzoyl chloride; 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 20℃; for 16h;
Stage #2: With piperidine In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; N-Fmoc L-Phe; Fmoc-Tyr(tBu)-OH Further stages;
100%
C35H34N4O5

C35H34N4O5

acetic anhydride
108-24-7

acetic anhydride

Fmoc-Ile-OH
71989-23-6

Fmoc-Ile-OH

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

Fmoc-Tyr(tBu)-OH

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

C79H111N15O14S2

C79H111N15O14S2

Conditions
ConditionsYield
Stage #1: Fmoc-Tyr(tBu)-OH 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 20℃; for 1h;
Stage #2: With piperidine In N,N-dimethyl-formamide at 20℃; for 0.2h;
Stage #3: C35H34N4O5; acetic anhydride; Fmoc-Ile-OH; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine Further stages;
100%
C50H67N10O9PolS

C50H67N10O9PolS

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

Fmoc-Tyr(tBu)-OH

C78H94N11O13PolS

C78H94N11O13PolS

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine for 0.833333h;99.5%
pentafluorophenyl trifloroacetate
14533-84-7

pentafluorophenyl trifloroacetate

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

Fmoc-Tyr(tBu)-OH

Fmoc-Tyr(tBu)-OPfp
86060-93-7

Fmoc-Tyr(tBu)-OPfp

Conditions
ConditionsYield
With pyridine In N,N-dimethyl-formamide for 0.75h; Ambient temperature;99%
Fmoc-Tyr(tBu)-OH
71989-38-3

Fmoc-Tyr(tBu)-OH

phenacyl 4-(hydroxymethyl)benzoate
136581-11-8

phenacyl 4-(hydroxymethyl)benzoate

Phenacyl 4-<<oxy>methyl>benzoate

Phenacyl 4-<methyl>benzoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane 1.) 0 deg C, 2 h, 2.) r.t., 18 h;99%
(4-(hydroxymethyl)phenyl)diphenylphosphine oxide
5068-20-2

(4-(hydroxymethyl)phenyl)diphenylphosphine oxide

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

Fmoc-Tyr(tBu)-OH

C47H44NO6P

C47H44NO6P

Conditions
ConditionsYield
Stage #1: (4-(hydroxymethyl)phenyl)diphenylphosphine oxide; Fmoc-Tyr(tBu)-OH 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-Tyr(tBu)-OH
71989-38-3

Fmoc-Tyr(tBu)-OH

2,4,6-trivinylcyclotriboroxane*pyridine complex

2,4,6-trivinylcyclotriboroxane*pyridine complex

(L)-N-Fmoc-tyrosine(OtBu) vinyl ester

(L)-N-Fmoc-tyrosine(OtBu) vinyl ester

Conditions
ConditionsYield
With N,N'-diethylurea; copper(II) bis(trifluoromethanesulfonate); triethylamine In tetrahydrofuran at 50℃; for 16h; Chan-Lam Coupling;99%
N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N6-tetradecanethioyl-L-lysine

N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N6-tetradecanethioyl-L-lysine

acetic anhydride
108-24-7

acetic anhydride

Fmoc-Ile-OH
71989-23-6

Fmoc-Ile-OH

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

Fmoc-Tyr(tBu)-OH

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

Ac-R(Pbf)IK(thioMis)R(Pbf)Y(tBu)-NH2*

Ac-R(Pbf)IK(thioMis)R(Pbf)Y(tBu)-NH2*

Conditions
ConditionsYield
Stage #1: Fmoc-Tyr(tBu)-OH 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 20℃; for 1h;
Stage #2: With piperidine In N,N-dimethyl-formamide at 20℃; for 0.2h;
Stage #3: N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N6-tetradecanethioyl-L-lysine; acetic anhydride; Fmoc-Ile-OH; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine Further stages;
99%
Fmoc-Leu-OH
35661-60-0

Fmoc-Leu-OH

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

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

Fmoc-Pro-OH
71989-31-6

Fmoc-Pro-OH

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

Fmoc-Glu(OtBu)-OH

Fmoc-Gly-NH2
115057-37-9

Fmoc-Gly-NH2

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

Fmoc-Tyr(tBu)-OH

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

Fmoc-Thr(tBu)-OH

H2N-YALPETG-CONH2
1419234-17-5

H2N-YALPETG-CONH2

Conditions
ConditionsYield
Stage #1: Fmoc-Gly-NH2 With 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: With piperidine In dichloromethane at 20℃; for 0.0333333h;
Stage #3: Fmoc-Leu-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; Fmoc-Pro-OH; Fmoc-Glu(OtBu)-OH; Fmoc-Tyr(tBu)-OH; Fmoc-Thr(tBu)-OH Further stages;
98%
N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Fmoc-Leu-OH
35661-60-0

Fmoc-Leu-OH

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

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

Fmoc-Pro-OH
71989-31-6

Fmoc-Pro-OH

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

Fmoc-Glu(OtBu)-OH

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

Fmoc-Tyr(tBu)-OH

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

Fmoc-Thr(tBu)-OH

H2N-Y-ALPETGG-COOH

H2N-Y-ALPETGG-COOH

Conditions
ConditionsYield
Stage #1: N-(fluoren-9-ylmethoxycarbonyl)glycine With 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: With piperidine In dichloromethane at 20℃; for 0.0333333h;
Stage #3: Fmoc-Leu-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; Fmoc-Pro-OH; Fmoc-Glu(OtBu)-OH; Fmoc-Tyr(tBu)-OH; Fmoc-Thr(tBu)-OH Further stages;
98%
Fmoc-Tyr(tBu)-OH
71989-38-3

Fmoc-Tyr(tBu)-OH

O-t-Butyl-L-tyrosine
4727-00-8, 18822-59-8

O-t-Butyl-L-tyrosine

Conditions
ConditionsYield
With sodium azide In N,N-dimethyl-formamide at 50℃; for 5h;98%
N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

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

Fmoc-Ser(tBu)-OH

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

Fmoc-Tyr(tBu)-OH

Fmoc-D(*)-OH

Fmoc-D(*)-OH

C29H37N7O11

C29H37N7O11

Conditions
ConditionsYield
Stage #1: N-(fluoren-9-ylmethoxycarbonyl)glycine With 1-methyl-pyrrolidin-2-one; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine at 20℃; for 0.5h;
Stage #2: With piperidine for 0.0833333h;
Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Ser(tBu)-OH; Fmoc-Tyr(tBu)-OH; Fmoc-D(*)-OH Further stages;
98%
fmoc-Lys(Boc)-Wang resin

fmoc-Lys(Boc)-Wang resin

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

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

Fmoc-Pro-OH
71989-31-6

Fmoc-Pro-OH

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

Fmoc-Ser(tBu)-OH

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

Fmoc-Tyr(tBu)-OH

Fmoc-Lys(tert-butoxycarbonyl)
71989-26-9

Fmoc-Lys(tert-butoxycarbonyl)

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

Fmoc-Thr(tBu)-OH

(2S,4R)-4-tert-butoxy-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carboxylic acid

(2S,4R)-4-tert-butoxy-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carboxylic acid

Ala-Lys-Pro-Ser-Tyr-Hyp-Hyp-Thr-Tyr-Lys
119106-85-3

Ala-Lys-Pro-Ser-Tyr-Hyp-Hyp-Thr-Tyr-Lys

Conditions
ConditionsYield
Stage #1: fmoc-Lys(Boc)-Wang resin With piperidine In N,N-dimethyl-formamide for 0.25h; Wang resin;
Stage #2: Fmoc-Tyr(tBu)-OH With O-(benzotriazol-1-yl)- N,N,N’,N’-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 1h; Wang resin;
Stage #3: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; Fmoc-Pro-OH; Fmoc-Ser(tBu)-OH; Fmoc-Tyr(tBu)-OH; Fmoc-Lys(tert-butoxycarbonyl); Fmoc-Thr(tBu)-OH; (2S,4R)-4-tert-butoxy-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carboxylic acid Further stages;
97.89%
N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

Fmoc-(tBu)Asp-OH
71989-14-5

Fmoc-(tBu)Asp-OH

Fmoc-Ile-OH
71989-23-6

Fmoc-Ile-OH

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

Fmoc-Tyr(tBu)-OH

Fmoc-Lys(tert-butoxycarbonyl)
71989-26-9

Fmoc-Lys(tert-butoxycarbonyl)

H-Val-Lys-Asp-Gly-Tyr-Ile-OH

H-Val-Lys-Asp-Gly-Tyr-Ile-OH

Conditions
ConditionsYield
Stage #1: Fmoc-Ile-OH With 17α-acetoxy-6-formyl-3-methoxypregna-3,5-dien-20-one; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 20 - 65℃; for 0.333333h; Microwave irradiation;
Stage #2: With piperazine; formic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃; for 0.25h;
Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Val-OH; Fmoc-(tBu)Asp-OH; Fmoc-Tyr(tBu)-OH; Fmoc-Lys(tert-butoxycarbonyl) Further stages;
97.6%
Stage #1: Fmoc-Ile-OH With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide Automated synthesizer;
Stage #2: With piperidine In N,N-dimethyl-formamide Automated synthesizer;
Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Val-OH; Fmoc-(tBu)Asp-OH; Fmoc-Tyr(tBu)-OH; Fmoc-Lys(tert-butoxycarbonyl) Further stages;
(S)-methyl 2-amino-6-(benzyloxycarbonylamino)hexanoate
24498-31-5

(S)-methyl 2-amino-6-(benzyloxycarbonylamino)hexanoate

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

Fmoc-Tyr(tBu)-OH

Fmoc-Tyr(tBu)-Lys(Z)-OMe
908120-74-1

Fmoc-Tyr(tBu)-Lys(Z)-OMe

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane for 8h;97.5%
N-benzyl-2,2-dimethoxyethylamine
54879-88-8

N-benzyl-2,2-dimethoxyethylamine

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

Fmoc-Tyr(tBu)-OH

C39H44N2O6
1083074-14-9

C39H44N2O6

Conditions
ConditionsYield
With N'-methyl polystyrene; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Inert atmosphere;97%
N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

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

C29H37N7O6
1454659-75-6

C29H37N7O6

Conditions
ConditionsYield
Stage #1: Fmoc-Leu-OH With pyridine; 2,6-dichlorobenzaldehyde In N,N-dimethyl-formamide
Stage #2: With pyridine; benzoyl chloride In N,N-dimethyl-formamide
Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; N-Fmoc L-Phe; Fmoc-Tyr(tBu)-OH Further stages;
97%
4,7,10-trioxa-1,13-diaminotridecane
4246-51-9

4,7,10-trioxa-1,13-diaminotridecane

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

Fmoc-Tyr(tBu)-OH

C66H78N4O11
1402012-45-6

C66H78N4O11

Conditions
ConditionsYield
Stage #1: Fmoc-Tyr(tBu)-OH With benzotriazol-1-ol In N,N-dimethyl-formamide at 20℃; for 0.166667h;
Stage #2: 4,7,10-trioxa-1,13-diaminotridecane In N,N-dimethyl-formamide at 20℃; for 0.5h;
97%
4-((1,3-bis(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyloxy)propan-2-yloxy)methyl)benzenemethanol

4-((1,3-bis(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyloxy)propan-2-yloxy)methyl)benzenemethanol

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

Fmoc-Tyr(tBu)-OH

C55H49F26NO8

C55H49F26NO8

Conditions
ConditionsYield
Stage #1: 4-((1,3-bis(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyloxy)propan-2-yloxy)methyl)benzenemethanol; Fmoc-Tyr(tBu)-OH In dichloromethane for 0.166667h; Cooling with ice;
Stage #2: With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 3.5h;
97%
Dimethyl-(3-methyl-2-butenyl)-sulfonium tetrafluoroborate

Dimethyl-(3-methyl-2-butenyl)-sulfonium tetrafluoroborate

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

Fmoc-Tyr(tBu)-OH

Fmoc-Tyr(t-Bu)-1,1-dimethylallyl ester
851713-94-5

Fmoc-Tyr(t-Bu)-1,1-dimethylallyl ester

Conditions
ConditionsYield
Stage #1: Fmoc-Tyr(tBu)-OH With sodium carbonate In dichloromethane for 0.0833333h;
Stage #2: Dimethyl-(3-methyl-2-butenyl)-sulfonium tetrafluoroborate With copper(I) bromide In dichloromethane at 20℃; Inert atmosphere; regioselective reaction;
96%
With potassium carbonate; copper(I) bromide In dichloromethane at 20℃;90%
(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-methyloct-7-enoic acid

(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-methyloct-7-enoic acid

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

N-(fluoren-9-ylmethoxycarbonyl)glycine

Fmoc-Leu-OH
35661-60-0

Fmoc-Leu-OH

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

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

N-Fmoc L-Phe
35661-40-6

N-Fmoc L-Phe

Fmoc-Ile-OH
71989-23-6

Fmoc-Ile-OH

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

Fmoc-Tyr(tBu)-OH

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

Fmoc-Thr(tBu)-OH

Fmoc-Arg(Pbf)-OH
119831-72-0

Fmoc-Arg(Pbf)-OH

3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester
143824-78-6

3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester

C78H117N17O14

C78H117N17O14

Conditions
ConditionsYield
Stage #1: 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester With diisopropyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 2h; amide resin;
Stage #2: With piperidine In N,N-dimethyl-formamide at 20℃; for 0.5h; amide resin;
Stage #3: (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-methyloct-7-enoic acid; N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Leu-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; N-Fmoc L-Phe; Fmoc-Ile-OH; Fmoc-Tyr(tBu)-OH; Fmoc-Thr(tBu)-OH; Fmoc-Arg(Pbf)-OH Further stages;
96%
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-Leu-Tyr(tBu)-Val-Gly-Thr(tBu)-Phe-OH

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

Conditions
ConditionsYield
Stage #1: Fmoc-Leu-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; N-Fmoc L-Phe; Fmoc-Tyr(tBu)-OH; Fmoc-Thr(tBu)-OH Further stages;
96%

71989-38-3Relevant articles and documents

Fungal Dioxygenase AsqJ Is Promiscuous and Bimodal: Substrate-Directed Formation of Quinolones versus Quinazolinones

Einsiedler, Manuel,Jamieson, Cooper S.,Maskeri, Mark A.,Houk, Kendall N.,Gulder, Tobias A. M.

supporting information, p. 8297 - 8302 (2021/03/01)

Previous studies showed that the FeII/α-ketoglutarate dependent dioxygenase AsqJ induces a skeletal rearrangement in viridicatin biosynthesis in Aspergillus nidulans, generating a quinolone scaffold from benzo[1,4]diazepine-2,5-dione substrates. We report that AsqJ catalyzes an additional, entirely different reaction, simply by a change in substituent in the benzodiazepinedione substrate. This new mechanism is established by substrate screening, application of functional probes, and computational analysis. AsqJ excises H2CO from the heterocyclic ring structure of suitable benzo[1,4]diazepine-2,5-dione substrates to generate quinazolinones. This novel AsqJ catalysis pathway is governed by a single substituent within the complex substrate. This unique substrate-directed reactivity of AsqJ enables the targeted biocatalytic generation of either quinolones or quinazolinones, two alkaloid frameworks of exceptional biomedical relevance.

Supported Catalytically Active Supramolecular Hydrogels for Continuous Flow Chemistry

Rodon Fores, Jennifer,Criado-Gonzalez, Miryam,Chaumont, Alain,Carvalho, Alain,Blanck, Christian,Schmutz, Marc,Serra, Christophe A.,Boulmedais,Schaaf, Pierre,Jierry, Lo?c

supporting information, p. 18817 - 18822 (2019/11/16)

Inspired by biology, one current goal in supramolecular chemistry is to control the emergence of new functionalities arising from the self-assembly of molecules. In particular, some peptides can self-assemble and generate exceptionally catalytically active fibrous networks able to underpin hydrogels. Unfortunately, the mechanical fragility of these materials is incompatible with process developments, relaying this exciting field to academic curiosity. Here, we show that this drawback can be circumvented by enzyme-assisted self-assembly of peptides initiated at the walls of a supporting porous material. We applied this strategy to grow an esterase-like catalytically active supramolecular hydrogel (CASH) in an open-cell polymer foam, filling the whole interior space. Our supported CASH material is highly efficient towards inactivated esters and enables the kinetic resolution of racemates. This hybrid material is robust enough to be used in continuous flow reactors, and is reusable and stable over months.

A one-pot procedure for the preparation of N-9-fluorenylmethyloxycarbonyl- α-amino diazoketones from α-amino acids

Siciliano, Carlo,De Marco, Rosaria,Guidi, Ludovica Evelin,Spinella, Mariagiovanna,Liguori, Angelo

, p. 10575 - 10582 (2013/02/22)

The study describes a new "one-pot" route to the synthesis of N-9-fluorenylmethyloxycarbonyl (Fmoc) α-amino diazoketones. The procedure was tested on a series of commercially available free or side-chain protected α-amino acids employed as precursors. The conversion into the title compounds was achieved by masking and activating the α-amino acids with a single reagent, namely, 9-fluorenylmethyl chloroformate (Fmoc-Cl). The resulting N-protected mixed anhydrides were reacted with diazomethane to lead to the α-amino diazoketones, which were isolated by flash column chromatography in very good to excellent overall yields. The versatility of the procedure was verified on lipophilic α-amino acids and further demonstrated by the preparation of N-Fmoc-α-amino diazoketones also from α-amino acids containing side-chain masking groups, which are orthogonal to the Fmoc one. The results confirmed that tert-butyloxycarbonyl (Boc), tert-butyl (tBu), and 2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl (Pbf), three acid-labile protecting groups mostly adopted in the solution and solid-phase peptide synthesis, are compatible to the adopted reaction conditions. In all cases, the formation of the corresponding C-methyl ester of the starting amino acid was not observed. Moreover, the proposed method respects the chirality of the starting α-amino acids. No racemization occurred when the procedure was applied to the synthesis of the respective N-Fmoc-protected α-amino diazoketones from l-isoleucine and l-threonine and to the preparation of a diastereomeric pair of N-Fmoc-protected dipeptidyl diazoketones.

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