N-Fmoc-N'-Boc-L-2,4-diaminobutyric acid supplier

Name
FMOC-DAB(BOC)-OH
EINECS 1533716-785-6
CAS No. 125238-99-5
Article Data4
CAS DataBase
Density 1.243 g/cm³
Solubility Slightly soluble in water.
Melting Point 111-113℃
Formula C₂₄H₂₈N₂O₆
Boiling Point 670.9 °C at 760 mmHg
Molecular Weight 440.496
Flash Point 359.6 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols Xi
Synonyms Butanoicacid, 4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-,(S)-;(S)-2-[[(9-Fluorenylmethoxy)carbonyl]amino]-4-(tert-butoxycarbonylamino)butanoicacid;(S)-4-[(tert-Butoxycarbonyl)amino]-2-[[[(9H-fluoren-9-yl)methoxy]carbonyl]amino]butanoicacid;
PSA 113.96000
LogP 4.67490

Synthetic route

: 24424-99-5
di-tert-butyl dicarbonate

: 161420-87-7
Nα-(9-fluorenylmethoxycarbonyl)-L-2,4-diaminobutyric acid

: 125238-99-5
(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid

Conditions

Conditions	Yield
With sodium hydroxide In water; acetone at 0 - 10℃; for 4h; pH=7.5 - 8; pH-value;	86.62%
With triethylamine In water; dimethyl sulfoxide	74.2%
With sodium hydrogencarbonate In water; acetonitrile for 6h; Yield given;

: (S)-(3-fluoren-9-yl-9-methoxycarbonyl)-4-[2-(tert-butyloxycarbonylamino)ethyl]-5-oxazolidinone

: 125238-99-5
(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid

Conditions

Conditions	Yield
With lithium hydroxide In tetrahydrofuran at 20℃;	73%

: 918428-66-7
9H-9-fluorenylmethyl (4S)-4-(3-azido-2-oxopropyl)-5-oxo-1,3-oxazolone-3-carboxylate

: 125238-99-5
(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 88 percent / toluene / 0.25 h / microwave irradiation 2: 73 percent / LiOH / tetrahydrofuran / 20 °C View Scheme

: 159530-17-3
Nα-Fmoc-Glu-5-oxazolidinone

: 125238-99-5
(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 94 percent / N-methylmorpholine; IBC-Cl; NaN3 / tetrahydrofuran / 0.5 h / -10 °C 2: 88 percent / toluene / 0.25 h / microwave irradiation 3: 73 percent / LiOH / tetrahydrofuran / 20 °C View Scheme

: 71989-20-3
N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine

Fmoc-Ala: Fmoc-Ala

: 125238-99-5
(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 88.9 percent / I,I-bis(trifluoroacetoxy)iodobenzene; H2O / dimethylsulfoxide / 20 h 2: 74.2 percent / triethylamine / H2O; dimethylsulfoxide View Scheme

: 71989-20-3
N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine

: 125238-99-5
(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine; bis-[(trifluoroacetoxy)iodo]benzene / 1.) CH3CN, H2O, 60 deg C, 2.) CH3CN, H2O, 60 deg C, 5 h 2: sodium hydrogencarbonate / water; acetonitrile / 6 h View Scheme

: 186581-53-3, 908094-01-9
diazomethane

: 125238-99-5
(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid

: 125218-68-0
Fmoc-L-Dbu(Boc)-OCH3

Conditions

Conditions	Yield
In diethyl ether for 0.166667h; Methylation;	100%

: 125238-99-5
(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid

: 100-46-9
benzylamine

: 316152-95-1
(9H-fluoren-9-yl)methyl tert-butyl (4-(benzylamino)-4-oxobutane-1,3-diyl)(S)-dicarbamate

Conditions

Conditions	Yield
With benzotriazol-1-ol; diisopropyl-carbodiimide In DMF (N,N-dimethyl-formamide); dichloromethane at 35℃;	100%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 2h; Inert atmosphere;	98%
Stage #1: (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid With benzotriazol-1-ol; diisopropyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide for 0.0833333h; Stage #2: benzylamine In dichloromethane; N,N-dimethyl-formamide at 35℃;	98%
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In acetonitrile at 20℃; for 3h;	14.4 g
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In acetonitrile at 20℃; for 2.5h;

: 65864-22-4
(S)-2-amino-3-phenylpropionamide hydrochloride

: 125238-99-5
(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid

: 849948-77-2
(1'S, 2S)-4-(N-Boc-amino)-N'-(1'-carbamoyl-2'-phenylethyl)-2-(N''-Fmoc-amino)butanamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; triethylamine; diisopropyl-carbodiimide In DMF (N,N-dimethyl-formamide); dichloromethane	100%
With benzotriazol-1-ol; triethylamine; diisopropyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide for 16h;

: 125238-99-5
(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid

: 13078-79-0
2-(3-chlorophenyl)ethylamine

: 849948-71-6
4-(N-Boc-amino)-N'-2-(3-chlorophenyl)ethyl-(S)-2-(N''-Fmoc-amino)butanamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; diisopropyl-carbodiimide In DMF (N,N-dimethyl-formamide); dichloromethane at 35℃;	100%

: 100-39-0
benzyl bromide

: 125238-99-5
(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid

: 668985-69-1
Fmoc-L-Dab(Boc)-OBn

Conditions

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 0 - 25℃; for 26h;	98%

: 125238-99-5
(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid

: HCl*H-Amn-Glu(OBzl)-Gly-OAll

: Fmoc-Dab(Boc)-Amn-Glu(OBzl)-Gly-OAll

Conditions

Conditions	Yield
With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide for 6h; Ambient temperature;	95.4%

: 152120-55-3
N,N-bis(benzyloxycarbonyl)-1H-pyrazole-1-carboxamidine

: 125238-99-5
(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid

: 76-05-1
trifluoroacetic acid

: 1573112-63-6
C21H24N4O6*C2HF3O2

Conditions

Conditions	Yield
Stage #1: (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid With N-ethyl-N,N-diisopropylamine In dichloromethane Stage #2: With piperidine In N,N-dimethyl-formamide Stage #3: N,N-bis(benzyloxycarbonyl)-1H-pyrazole-1-carboxamidine; trifluoroacetic acid Further stages;	95.2%

...Expand

: 50881-96-4
morpholine 4-carboxylic acid

: 125238-99-5
(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid

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

: 1276031-39-0
C23H40N4O7

Conditions

Conditions	Yield
Stage #1: (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.5h; Stage #3: morpholine-4-carboxylic acid; (S)-3-cyclohexyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propionic acid Further stages;	95%

...Expand

: methyl (4S,7S,10S)-16,25-bis(2-((tert-butoxycarbonyl)amino)ethoxy)-26-methoxy-7-methyl-10-(methylamino)-6,9-dioxo-5,8-diaza-1,2(1,3)-dibenzenacyclodecaphane-4-carboxylate

: 125238-99-5
(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid

: methyl (4S,7S,10S)-10-((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-((tert-butoxycarbonyl)amino)-N-methylbutanamido)-16,25-bis(2-((tert-butoxycarbonyl)amino)ethoxy)-26-methoxy-7-methyl-6,9-dioxo-5,8-diaza-1,2(1,3)-dibenzenacyclodecaphane-4-carboxylate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.5h;	95%

: C49H45N3O4S3

: 125238-99-5
(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid

: C73H71N5O9S3

Conditions

Conditions	Yield
Stage #1: (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid With 2,4,6-trichlorobenzoyl chloride; triethylamine In tetrahydrofuran at 0℃; for 2h; Stage #2: C49H45N3O4S3 With dmap In tetrahydrofuran at 0 - 25℃; for 1h;	91%

: methyl (4S,7S,10S)-16-(2-((tert-butoxycarbonyl)amino)ethoxy)-26-hydroxy-7-methyl-10-(methylamino)-6,9-dioxo-5,8-diaza-1,2(1,3)-dibenzenacyclodecaphane-4-carboxylate

: 125238-99-5
(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid

: methyl (4S,7S,10S)-10-((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-((tert-butoxycarbonyl)amino)-N-methylbutanamido)-16-(2-((tert-butoxycarbonyl)amino)ethoxy)-26-hydroxy-7-methyl-6,9-dioxo-5,8-diaza-1,2(1,3)-dibenzenacyclodecaphane-4-carboxylate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In tetrahydrofuran at 50℃; for 12h; Inert atmosphere;	89%
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate at 20℃; for 4h; Inert atmosphere;	78%

: 106-95-6
allyl bromide

: 125238-99-5
(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid

: Fmoc-L-Dab(Boc)-OAllyl, Dab = 2,4-diaminobutyric acid

Conditions

Conditions	Yield
With Aliquat (at)366; sodium hydrogencarbonate In dichloromethane; water at 20℃;	83%
With Aliquat 336; sodium hydrogencarbonate In dichloromethane; water at 20℃;

: EB-NH2

: 125238-99-5
(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid

: C48H48N6O12S2

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide for 24h;	80%

: 20924-05-4
thymidyl acetic acid

: 125238-99-5
(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid

: C26H26N4O7

Conditions

Conditions	Yield
Stage #1: (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid With trifluoroacetic acid In dichloromethane at 45℃; for 1h; Stage #2: thymidyl acetic acid With 2,4,6-trimethyl-pyridine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In 1-methyl-pyrrolidin-2-one for 1.5h;	80%

Yield

Stage #1: (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid With trifluoroacetic acid In dichloromethane at 45℃; for 1h;
Stage #2: thymidyl acetic acid With 2,4,6-trimethyl-pyridine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In 1-methyl-pyrrolidin-2-one for 1.5h;

80%

: 1447274-12-5
methyl 2'-(3'-(4-(aminomethyl)-[2,4'-bioxazol]-2'-yl)-[1,1'-biphenyl]-3-yl)-[2,4'-bioxazole]-4-carboxylate

: 125238-99-5
(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid

: 1447274-28-3
methyl 2'-(3'-(4-((2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(((tert-butoxy)carbonyl)amino)butanamido)methyl)-[2,4'-bioxazol]-2'-yl)-[1,1'-biphenyl]-3-yl)-[2,4'-bioxazol]-4-carboxylate

Conditions

Conditions	Yield
Stage #1: (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 0.0833333h; Inert atmosphere; Stage #2: methyl 2'-(3'-(4-(aminomethyl)-[2,4'-bioxazol]-2'-yl)-[1,1'-biphenyl]-3-yl)-[2,4'-bioxazole]-4-carboxylate With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	78%

Yield

Stage #1: (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 0.0833333h; Inert atmosphere;
Stage #2: methyl 2'-(3'-(4-(aminomethyl)-[2,4'-bioxazol]-2'-yl)-[1,1'-biphenyl]-3-yl)-[2,4'-bioxazole]-4-carboxylate With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;

78%

: 35661-60-0
Fmoc-Leu-OH

: 35661-40-6
N-Fmoc L-Phe

: 125238-99-5
(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid

: N-α-(9-fluorenylmethyloxycarbonyl)-N-γ-tert-butyloxycarbonyl-D-2,4-diaminobutyric acid

: NH2-D-Dab-L-Dab-L-Dab-L-Leu-D-Phe-L-Dab-L-Dab-L-Leu-NH2

Conditions

Conditions	Yield
Stage #1: Fmoc-Leu-OH With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 50℃; for 0.0833333h; Microwave irradiation; Stage #2: With piperidine In N,N-dimethyl-formamide at 75℃; for 0.1h; Microwave irradiation; Stage #3: Fmoc-Leu-OH; N-Fmoc L-Phe; (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid; N-α-(9-fluorenylmethyloxycarbonyl)-N-γ-tert-butyloxycarbonyl-D-2,4-diaminobutyric acid Further stages;	77%

Yield

Stage #1: Fmoc-Leu-OH With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 50℃; for 0.0833333h; Microwave irradiation;
Stage #2: With piperidine In N,N-dimethyl-formamide at 75℃; for 0.1h; Microwave irradiation;
Stage #3: Fmoc-Leu-OH; N-Fmoc L-Phe; (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid; N-α-(9-fluorenylmethyloxycarbonyl)-N-γ-tert-butyloxycarbonyl-D-2,4-diaminobutyric acid Further stages;

77%

...Expand

: methyl (4S,7S,10S)-26-(benzyloxy)-10-(((benzyloxy)carbonyl)(methyl)amino)-16-(2-((tert-butoxycarbonyl)amino)ethoxy)-25-fluoro-7-methyl-6,9-dioxo-5,8-diaza-1,2(1,3)-dibenzenacyclodecaphane-4-carboxylate

: 125238-99-5
(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid

: methyl (4S,7S,10S)-10-((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-((tert-butoxycarbonyl)amino)-N-methylbutanamido)-16-(2-((tert-butoxycarbonyl)amino)ethoxy)-25-fluoro-26-hydroxy-7-methyl-6,9-dioxo-5,8-diaza-1,2(1,3)-dibenzenacyclodecaphane-4-carboxylate

Conditions

Conditions	Yield
Stage #1: (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In tetrahydrofuran for 0.333333h; Stage #2: methyl (4S,7S,10S)-26-(benzyloxy)-10-(((benzyloxy)carbonyl)(methyl)amino)-16-(2-((tert-butoxycarbonyl)amino)ethoxy)-25-fluoro-7-methyl-6,9-dioxo-5,8-diaza-1,2(1,3)-dibenzenacyclodecaphane-4-carboxylate In tetrahydrofuran at 20℃; for 2h;	68%

Yield

Stage #1: (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In tetrahydrofuran for 0.333333h;
Stage #2: methyl (4S,7S,10S)-26-(benzyloxy)-10-(((benzyloxy)carbonyl)(methyl)amino)-16-(2-((tert-butoxycarbonyl)amino)ethoxy)-25-fluoro-7-methyl-6,9-dioxo-5,8-diaza-1,2(1,3)-dibenzenacyclodecaphane-4-carboxylate In tetrahydrofuran at 20℃; for 2h;

68%

: 1070774-52-5
(S)-2,4-dimethyl-pent-4-enoic acid

: 1070774-51-4
Fmoc-D-abrine

: 1070774-49-0
N-Fmoc-O-TIPS-β-tyrosine

: 125238-99-5
(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid

: C46H69N5O8Si

Conditions

Conditions	Yield
Stage #1: N-Fmoc-O-TIPS-β-tyrosine With N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 4h; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.25h; Stage #3: (S)-2,4-dimethyl-pent-4-enoic acid; Fmoc-D-abrine; (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid	65%

...Expand

: 118-31-0
(naphth-1-yl)methylamine

: 125238-99-5
(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid

: 369656-01-9
4-N-Boc-amino-(S)-2-N'-Fmoc-amino-N''-1-naphthylmethylbutanamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; diisopropyl-carbodiimide In DMF (N,N-dimethyl-formamide); dichloromethane at 50℃;	60%

: 3006-96-0
3-hydroxymethyl-benzoic acid

: 64-19-7
acetic acid

: 125238-99-5
(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid

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

: C17H20N4O3

Conditions

Conditions	Yield
Stage #1: 3-hydroxymethyl-benzoic acid With piperidine; N-ethylmorpholine;; N-[(1H-benzotriazol-1-yl)(dimethylamino)methylene]-N-methylmethanaminium tetrafluoroborate In N,N-dimethyl-formamide for 2.08333h; Stage #2: (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid With 1-methyl-1H-imidazole; 1-(mesitylene-2-sulfonyl)-3-nitro-1H-1,2,4-triazole In dichloromethane for 1.08333h; Stage #3: acetic acid; 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester Further stages;	59%

Yield

Stage #1: 3-hydroxymethyl-benzoic acid With piperidine; N-ethylmorpholine;; N-[(1H-benzotriazol-1-yl)(dimethylamino)methylene]-N-methylmethanaminium tetrafluoroborate In N,N-dimethyl-formamide for 2.08333h;
Stage #2: (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid With 1-methyl-1H-imidazole; 1-(mesitylene-2-sulfonyl)-3-nitro-1H-1,2,4-triazole In dichloromethane for 1.08333h;
Stage #3: acetic acid; 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester Further stages;

59%

...Expand

: 1561-11-1
4-methylhexanoic acid

: 35661-60-0
Fmoc-Leu-OH

: 35661-40-6
N-Fmoc L-Phe

: 125238-99-5
(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid

: N-α-(9-fluorenylmethyloxycarbonyl)-N-γ-tert-butyloxycarbonyl-D-2,4-diaminobutyric acid

: C48H86N14O9

Conditions

Conditions	Yield
Stage #1: Fmoc-Leu-OH With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 50℃; for 0.0833333h; Microwave irradiation; Stage #2: With piperidine In N,N-dimethyl-formamide at 75℃; for 0.1h; Microwave irradiation; Stage #3: 4-methylhexanoic acid; Fmoc-Leu-OH; N-Fmoc L-Phe; (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid; N-α-(9-fluorenylmethyloxycarbonyl)-N-γ-tert-butyloxycarbonyl-D-2,4-diaminobutyric acid Further stages;	58%

Yield

Stage #1: Fmoc-Leu-OH With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 50℃; for 0.0833333h; Microwave irradiation;
Stage #2: With piperidine In N,N-dimethyl-formamide at 75℃; for 0.1h; Microwave irradiation;
Stage #3: 4-methylhexanoic acid; Fmoc-Leu-OH; N-Fmoc L-Phe; (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid; N-α-(9-fluorenylmethyloxycarbonyl)-N-γ-tert-butyloxycarbonyl-D-2,4-diaminobutyric acid Further stages;

58%

...Expand

: 120205-48-3
tert-Butyl (3R,4S,5S)-3-methoxy-4-(N-methylamino)-5-methylheptanoate hydrochloride

: 125238-99-5
(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid

: Fmoc-Dab(Boc)-Dil-OtBu

Conditions

Conditions	Yield
Stage #1: tert-Butyl (3R,4S,5S)-3-methoxy-4-(N-methylamino)-5-methylheptanoate hydrochloride; (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid With N-ethyl-N,N-diisopropylamine In ethyl acetate at 0℃; for 0.666667h; Stage #2: With 2-chloro-1-methyl-pyridinium iodide In ethyl acetate at 0 - 20℃; for 12h;	51%

: 617-79-8
2-ethyl-N-butylamine

: 1187487-23-5
benzyl 2-oxobut-3-enylcarbamate

: 125238-99-5
(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid

: 1185654-07-2
(S)-9-fluorenylmethyl 10-(2-ethylbutyl)-2,2-dimethyl-18-phenyl-4,9,13,16-tetraoxo-3,17-dioxa-5,10,15-triazaoctadecan-8-ylcarbamate

Conditions

Conditions	Yield
Stage #1: 2-ethyl-N-butylamine; benzyl 2-oxobut-3-enylcarbamate In dichloromethane at 20℃; for 0.25h; Stage #2: (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid With diisopropyl-carbodiimide In dichloromethane at 20℃;	46%
Stage #1: 2-ethyl-N-butylamine; benzyl 2-oxobut-3-enylcarbamate In dichloromethane at 20℃; for 0.25h; Stage #2: (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid With diisopropyl-carbodiimide In dichloromethane at 20℃;	46%

...Expand

: 27144-18-9
3-(tritylthio) propanoic acid

: 35661-60-0
Fmoc-Leu-OH

: 35661-40-6
N-Fmoc L-Phe

: 125238-99-5
(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid

: N-α-(9-fluorenylmethyloxycarbonyl)-N-γ-tert-butyloxycarbonyl-D-2,4-diaminobutyric acid

: C44H78N14O9S

Conditions

Conditions	Yield
Stage #1: Fmoc-Leu-OH With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 50℃; for 0.0833333h; Microwave irradiation; Stage #2: With piperidine In N,N-dimethyl-formamide at 75℃; for 0.1h; Microwave irradiation; Stage #3: 3-(tritylthio) propanoic acid; Fmoc-Leu-OH; N-Fmoc L-Phe; (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid; N-α-(9-fluorenylmethyloxycarbonyl)-N-γ-tert-butyloxycarbonyl-D-2,4-diaminobutyric acid Further stages;	32%

Yield

Stage #1: Fmoc-Leu-OH With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 50℃; for 0.0833333h; Microwave irradiation;
Stage #2: With piperidine In N,N-dimethyl-formamide at 75℃; for 0.1h; Microwave irradiation;
Stage #3: 3-(tritylthio) propanoic acid; Fmoc-Leu-OH; N-Fmoc L-Phe; (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid; N-α-(9-fluorenylmethyloxycarbonyl)-N-γ-tert-butyloxycarbonyl-D-2,4-diaminobutyric acid Further stages;

32%

...Expand

: 1187487-23-5
benzyl 2-oxobut-3-enylcarbamate

: 3963-62-0
2,2-Diphenylethylamine

: 125238-99-5
(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid

: 1185653-49-9
(S)-9-fluorenylmethyl 10-(2,2-diphenylethyl)-2,2-dimethyl-18-phenyl-4,9,13,16-tetraoxo-3,17-dioxa-5,10,15-triazaoctadecan-8-ylcarbamate

Conditions

Conditions	Yield
Stage #1: benzyl 2-oxobut-3-enylcarbamate; 2,2-Diphenylethylamine In dichloromethane at 20℃; for 0.25h; Stage #2: (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid With diisopropyl-carbodiimide In dichloromethane at 20℃; Product distribution / selectivity;	31%
Stage #1: benzyl 2-oxobut-3-enylcarbamate; 2,2-Diphenylethylamine In dichloromethane at 20℃; for 0.25h; Stage #2: (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid With diisopropyl-carbodiimide In dichloromethane at 20℃; Product distribution / selectivity;	31%
Stage #1: benzyl 2-oxobut-3-enylcarbamate; 2,2-Diphenylethylamine In dichloromethane at 20℃; for 0.25h; Stage #2: (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid With diisopropyl-carbodiimide In dichloromethane at 20℃; Product distribution / selectivity;	31%

...Expand

: 929-10-2
isooctanoic acid

: Fmoc-L-Dab(Dde)-OH, DDE = 1-(4,4-dimethyl-2,6-dioxocylohexylidene)ethyl

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

: 86123-10-6
Fmoc-D-Phe-OH

: 125238-99-5
(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid

: 76-05-1
trifluoroacetic acid

: 688316-86-1
Fmoc-L-Dab-OAllyl, Dab = 2,4-diaminobutyric acid

Fmoc-D-Ser(pg)-OH: Fmoc-D-Ser(pg)-OH

: polymyxin S2 TFA salt

Conditions

Conditions	Yield
Stage #1: Fmoc-L-Dab-OAllyl, Dab = 2,4-diaminobutyric acid With N-ethyl-N,N-diisopropylamine In dichloromethane for 2h; 2-chlorotrityl chloride resin; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.25h; Automated synthesizer; Stage #3: isooctanoic acid; Fmoc-L-Dab(Dde)-OH, DDE = 1-(4,4-dimethyl-2,6-dioxocylohexylidene)ethyl; Fmoc-Thr(tBu)-OH; Fmoc-D-Phe-OH; (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid; trifluoroacetic acid; Fmoc-D-Ser(pg)-OH Further stages;	31%

Yield

Stage #1: Fmoc-L-Dab-OAllyl, Dab = 2,4-diaminobutyric acid With N-ethyl-N,N-diisopropylamine In dichloromethane for 2h; 2-chlorotrityl chloride resin;
Stage #2: With piperidine In N,N-dimethyl-formamide for 0.25h; Automated synthesizer;
Stage #3: isooctanoic acid; Fmoc-L-Dab(Dde)-OH, DDE = 1-(4,4-dimethyl-2,6-dioxocylohexylidene)ethyl; Fmoc-Thr(tBu)-OH; Fmoc-D-Phe-OH; (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid; trifluoroacetic acid; Fmoc-D-Ser(pg)-OH Further stages;

31%

...Expand

: 929-10-2
isooctanoic acid

: Fmoc-L-Dab(Dde)-OH, DDE = 1-(4,4-dimethyl-2,6-dioxocylohexylidene)ethyl

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

: 35661-60-0, 126727-03-5, 114360-54-2
N-(9-fluorenylmethoxycarbonyl)-D-leucine

: 125238-99-5
(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid

: 76-05-1
trifluoroacetic acid

: 688316-86-1
Fmoc-L-Dab-OAllyl, Dab = 2,4-diaminobutyric acid

Fmoc-D-Ser(pg)-OH: Fmoc-D-Ser(pg)-OH

: polymyxin D2 TFA salt

Conditions

Conditions	Yield
Stage #1: Fmoc-L-Dab-OAllyl, Dab = 2,4-diaminobutyric acid With N-ethyl-N,N-diisopropylamine In dichloromethane for 2h; 2-chlorotrityl chloride resin; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.25h; Automated synthesizer; Stage #3: isooctanoic acid; Fmoc-L-Dab(Dde)-OH, DDE = 1-(4,4-dimethyl-2,6-dioxocylohexylidene)ethyl; Fmoc-Thr(tBu)-OH; N-(9-fluorenylmethoxycarbonyl)-D-leucine; (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid; trifluoroacetic acid; Fmoc-D-Ser(pg)-OH Further stages;	30%

Yield

Stage #1: Fmoc-L-Dab-OAllyl, Dab = 2,4-diaminobutyric acid With N-ethyl-N,N-diisopropylamine In dichloromethane for 2h; 2-chlorotrityl chloride resin;
Stage #2: With piperidine In N,N-dimethyl-formamide for 0.25h; Automated synthesizer;
Stage #3: isooctanoic acid; Fmoc-L-Dab(Dde)-OH, DDE = 1-(4,4-dimethyl-2,6-dioxocylohexylidene)ethyl; Fmoc-Thr(tBu)-OH; N-(9-fluorenylmethoxycarbonyl)-D-leucine; (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid; trifluoroacetic acid; Fmoc-D-Ser(pg)-OH Further stages;

30%

...Expand

: 35661-60-0
Fmoc-Leu-OH

: 35661-40-6
N-Fmoc L-Phe

: 103213-32-7
N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine

: 125238-99-5
(S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid

: N-α-(9-fluorenylmethyloxycarbonyl)-N-γ-tert-butyloxycarbonyl-D-2,4-diaminobutyric acid

: C44H79N15O9S

Conditions

Conditions	Yield
Stage #1: Fmoc-Leu-OH With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 50℃; for 0.0833333h; Microwave irradiation; Stage #2: With piperidine In N,N-dimethyl-formamide at 75℃; for 0.1h; Microwave irradiation; Stage #3: Fmoc-Leu-OH; N-Fmoc L-Phe; N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine; (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid; N-α-(9-fluorenylmethyloxycarbonyl)-N-γ-tert-butyloxycarbonyl-D-2,4-diaminobutyric acid Further stages;	30%

Yield

Stage #1: Fmoc-Leu-OH With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 50℃; for 0.0833333h; Microwave irradiation;
Stage #2: With piperidine In N,N-dimethyl-formamide at 75℃; for 0.1h; Microwave irradiation;
Stage #3: Fmoc-Leu-OH; N-Fmoc L-Phe; N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine; (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid; N-α-(9-fluorenylmethyloxycarbonyl)-N-γ-tert-butyloxycarbonyl-D-2,4-diaminobutyric acid Further stages;

30%

...Expand

N-Fmoc-N'-Boc-L-2,4-diaminobutyric acid Chemical Properties

Product Name: N-Fmoc-N'-Boc-L-2,4-diaminobutyric acid
Molecular Structure:

Molecular Formula: C₂₄H₂₈N₂O₆
Molecular Weight: 440.4889
Synonyms of N-Fmoc-N'-Boc-L-2,4-diaminobutyric acid (CAS NO.125238-99-5): Rarechem em wb 0101 ; N-2-(9-fluorenylmethoxycarbonyl)-n-4-t-butoxycarbonyl-l-2,4-diaminobutyric acid ; Nalpha-fmoc-ngamma-boc-l-2,4-diaminobutyric acid ; N-Alpha-fmoc-n-gamma-boc-l-diaminobutyric acid ; N-Alpha-fmoc-n-gamma-t-boc-l-alpha,gamma-diaminobutyric acid ; N-Alpha-fmoc-n-gamma-t-boc-l-diaminobutanoic acid ; N-Alpha-fmoc-n-gamma-t-butyloxycarbonyl-(s)-2,4-diaminobutyric acid ; N-Alpha-(9-fluorenylmethyloxycarbonyl)-n-gamma-t-butyloxycarbonyl-l-2,4-diaminobutyric acid
CAS NO: 125238-99-5
Classification Code: Unusual amino acids ; Amino Acids ; amino acid
Index of Refraction: 1.575
Molar Refractivity: 117.04 cm³
Molar Volume: 354.1 cm³
Surface Tension: 51.4 dyne/cm
Density: 1.243 g/cm³
Flash Point: 359.6 °C
Enthalpy of Vaporization: 103.56 kJ/mol
Boiling Point: 670.9 °C at 760 mmHg
Vapour Pressure of N-Fmoc-N'-Boc-L-2,4-diaminobutyric acid (CAS NO.125238-99-5): 6.47E-19 mmHg at 25°C

N-Fmoc-N'-Boc-L-2,4-diaminobutyric acid Safety Profile

Hazard Codes of N-Fmoc-N'-Boc-L-2,4-diaminobutyric acid (CAS NO.125238-99-5): Xi
WGK Germany: 3
F: 10
HazardClass: IRRITANT

Product Name

FMOC-DAB(BOC)-OH

Synthetic route

N-Fmoc-N'-Boc-L-2,4-diaminobutyric acid Chemical Properties

N-Fmoc-N'-Boc-L-2,4-diaminobutyric acid Safety Profile

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