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CAS No.: | 87420-41-5 |
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Name: | N-ALPHA-PALMITOYL-S-[2,3-BIS(PALMITOYLOXY)-(2RS)-PROPYL]-L-CYSTEINE |
Article Data: | 3 |
Molecular Structure: | |
Formula: | C54H103 N O7 S |
Molecular Weight: | 910.48 |
Synonyms: | Hexadecanoicacid, 1-[[[(2R)-2-carboxy-2-[(1-oxohexadecyl)amino]ethyl]thio]methyl]-1,2-ethanediylester (9CI); Pam3Cys; S-[2,3-Bis(palmitoyloxy)propyl]-N-palmitoyl-L-cysteine |
Density: | 0.966g/cm3 |
Boiling Point: | 907.8°C at 760 mmHg |
Flash Point: | 502.8°C |
PSA: | 144.30000 |
LogP: | 16.57880 |
3-((R)-3-(allyloxy)-3-oxo-2-palmitamidopropylthio)propane-1,2-diyl dipalmitate
S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine
Conditions | Yield |
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With tetrakis(triphenylphosphine) palladium(0); N-methylaniline In tetrahydrofuran at 20℃; for 1h; | 97% |
With tetrakis(triphenylphosphine) palladium(0); N-methylaniline In tetrahydrofuran at 20℃; for 1h; | 97% |
(R)-allyl 2-(tert-butoxycarbonylamino)-3-((2,2-dimethyl-1,3-dioxolan-4-yl)methylthio)propanoate
S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine
Conditions | Yield |
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Multi-step reaction with 5 steps 1: acetic acid / 20 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 20 °C / Cooling with ice 3: trifluoroacetic acid / dichloromethane / 20 °C 4: 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 5: tetrakis(triphenylphosphine) palladium(0); N-methylaniline / tetrahydrofuran / 1 h / 20 °C View Scheme | |
Multi-step reaction with 5 steps 1: acetic acid / 20 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 20 °C / Cooling with ice 3: trifluoroacetic acid / dichloromethane / 20 °C 4: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 5: tetrakis(triphenylphosphine) palladium(0); N-methylaniline / tetrahydrofuran / 1 h / 20 °C View Scheme |
(R)-allyl 2-(tert-butoxycarbonylamino)-3-(2,3-dihydroxypropylthio)propanoate
S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine
Conditions | Yield |
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Multi-step reaction with 4 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 20 °C / Cooling with ice 2: trifluoroacetic acid / dichloromethane / 20 °C 3: 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 4: tetrakis(triphenylphosphine) palladium(0); N-methylaniline / tetrahydrofuran / 1 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 20 °C / Cooling with ice 2: trifluoroacetic acid / dichloromethane / 20 °C 3: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 4: tetrakis(triphenylphosphine) palladium(0); N-methylaniline / tetrahydrofuran / 1 h / 20 °C View Scheme |
3-((R)-3-(allyloxy)-2-amino-3-oxopropylthio)propane-1,2-diyl dipalmitate
1-hexadecylcarboxylic acid
S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine
Conditions | Yield |
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Multi-step reaction with 2 steps 1: 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2: tetrakis(triphenylphosphine) palladium(0); N-methylaniline / tetrahydrofuran / 1 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2: tetrakis(triphenylphosphine) palladium(0); N-methylaniline / tetrahydrofuran / 1 h / 20 °C View Scheme |
(2R)-3-(3-(allyloxy)-2-(tert-butoxycarbonylamino)-3-oxopropylthio)propane-1,2-diyl dipalmitate
S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine
Conditions | Yield |
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Multi-step reaction with 3 steps 1: trifluoroacetic acid / dichloromethane / 20 °C 2: 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 3: tetrakis(triphenylphosphine) palladium(0); N-methylaniline / tetrahydrofuran / 1 h / 20 °C View Scheme |
S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine
Conditions | Yield |
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Multi-step reaction with 3 steps 1: trifluoroacetic acid / dichloromethane / 20 °C 2: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 3: tetrakis(triphenylphosphine) palladium(0); N-methylaniline / tetrahydrofuran / 1 h / 20 °C View Scheme |
S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine
6-(amino)hexyl (α-D-mannopyranosyl)-(1->2)-O-(α-D-mannopyranosyl)-(1->2)-O-[(β-D-galactopyranosyl)-(1->4)]-α-D-mannopyranoside
Conditions | Yield |
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With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane; N,N-dimethyl-formamide at 20℃; for 20h; | 60% |
N-(fluoren-9-ylmethoxycarbonyl)glycine
Fmoc-Val-OH
Fmoc-Leu-OH
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine
N-Fmoc L-Phe
Fmoc-Ser(tBu)-OH
Fmoc-(tBu)Asp-OH
Fmoc-Glu(OtBu)-OH
Fmoc-Ile-OH
Fmoc-Lys(tert-butoxycarbonyl)
L-Asn(Trt)
Fmoc-L-Gln(Trt)-OH
S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine
Fmoc-Lys(Mmt)-OH
palmitoyl-Cys((RS)-2,3-di(palmitoyloxy)propyl)-Ser-Lys-Lys-Lys-Lys-Asp-Glu-Val-Ser-Gly-Leu-Glu-Gln-Leu-Glu-Ser-Ile-Ile-Asn-Phe-Glu-Lys-Leu-Ala-Ala-Ala-Ala-Ala-Lys-NH2
Conditions | Yield |
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Stage #1: Fmoc-Lys(Mmt)-OH With 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V) In N,N-dimethyl-formamide Stage #2: With piperidine In N,N-dimethyl-formamide Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Val-OH; Fmoc-Leu-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; N-Fmoc L-Phe; Fmoc-Ser(tBu)-OH; Fmoc-(tBu)Asp-OH; Fmoc-Glu(OtBu)-OH; Fmoc-Ile-OH; Fmoc-Lys(tert-butoxycarbonyl); L-Asn(Trt); Fmoc-L-Gln(Trt)-OH; S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine Further stages; | 5% |
H-Asn-Ser(But)-Gly-Gly-Ser(But)-OBut
S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine
S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-Cys-Asn-Ser(But)-Gly-Gly-Ser(But)-OBut
Conditions | Yield |
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With benzotriazol-1-ol; dicyclohexyl-carbodiimide 1) DMF, CH2Cl2, 30 min, ice-salt cooling 2) CH2Cl2, 15 h, r.t.; Yield given. Multistep reaction; |
S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine
Conditions | Yield |
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Stage #1: S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine With 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide for 0.333333h; Stage #2: C108H153N14O19PolS2 In dichloromethane; N,N-dimethyl-formamide at 20℃; for 20h; Stage #3: With chlorotriisopropylsilane; trifluoroacetic acid In dichloromethane; water; N,N-dimethyl-formamide for 3h; | 7.3 mg |