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87420-41-5

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Basic Information
CAS No.: 87420-41-5
Name: N-ALPHA-PALMITOYL-S-[2,3-BIS(PALMITOYLOXY)-(2RS)-PROPYL]-L-CYSTEINE
Article Data: 3
Molecular Structure:
Molecular Structure of 87420-41-5 (N-ALPHA-PALMITOYL-S-[2,3-BIS(PALMITOYLOXY)-(2RS)-PROPYL]-L-CYSTEINE)
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
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Synthetic route
1610431-29-2

3-((R)-3-(allyloxy)-3-oxo-2-palmitamidopropylthio)propane-1,2-diyl dipalmitate

87420-41-5

S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine

Conditions
ConditionsYield
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%
1610431-05-4

(R)-allyl 2-(tert-butoxycarbonylamino)-3-((2,2-dimethyl-1,3-dioxolan-4-yl)methylthio)propanoate

87420-41-5

S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine

Conditions
ConditionsYield
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
1610431-06-5

(R)-allyl 2-(tert-butoxycarbonylamino)-3-(2,3-dihydroxypropylthio)propanoate

87420-41-5

S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine

Conditions
ConditionsYield
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
1610431-28-1

3-((R)-3-(allyloxy)-2-amino-3-oxopropylthio)propane-1,2-diyl dipalmitate

57-10-3

1-hexadecylcarboxylic acid

87420-41-5

S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine

Conditions
ConditionsYield
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
1610431-07-6

(2R)-3-(3-(allyloxy)-2-(tert-butoxycarbonylamino)-3-oxopropylthio)propane-1,2-diyl dipalmitate

87420-41-5

S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine

Conditions
ConditionsYield
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

(R)-3-(3-(allyloxy)-2-(tert-butoxycarbonylamino)-3-oxopropylthio)propane-1,2-diyl dipalmitate

87420-41-5

S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine

Conditions
ConditionsYield
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
87420-41-5

S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine

351011-55-7

6-(amino)hexyl (α-D-mannopyranosyl)-(1->2)-O-(α-D-mannopyranosyl)-(1->2)-O-[(β-D-galactopyranosyl)-(1->4)]-α-D-mannopyranoside

6-(N-palmitoyl-S-[2,3-bis(palmitoyloxy)-(2R,2S)-propyl]-L-cystenyl)hexyl-(α-D-mannopyranosyl)-(1->2)-O-(α-D-mannopyranosyl)-(1->2)-O-[(β-D-galactopyranosyl)-(1->4)]-α-D-mannopyranoside

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane; N,N-dimethyl-formamide at 20℃; for 20h;60%
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

68858-20-8

Fmoc-Val-OH

35661-60-0

Fmoc-Leu-OH

35661-39-3

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

35661-40-6

N-Fmoc L-Phe

71989-33-8

Fmoc-Ser(tBu)-OH

71989-14-5

Fmoc-(tBu)Asp-OH

71989-18-9

Fmoc-Glu(OtBu)-OH

71989-23-6

Fmoc-Ile-OH

71989-26-9

Fmoc-Lys(tert-butoxycarbonyl)

132388-59-1

L-Asn(Trt)

132327-80-1

Fmoc-L-Gln(Trt)-OH

87420-41-5

S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine

159857-60-0

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

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
ConditionsYield
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%
...Expand
134982-15-3

H-Asn-Ser(But)-Gly-Gly-Ser(But)-OBut

87420-41-5

S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine

142292-21-5

S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-Cys-Asn-Ser(But)-Gly-Gly-Ser(But)-OBut

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide 1) DMF, CH2Cl2, 30 min, ice-salt cooling 2) CH2Cl2, 15 h, r.t.; Yield given. Multistep reaction;

C108H153N14O19PolS2

87420-41-5

S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-Nα-palmitoyl-cysteine

N-palmitoyl-S-[2,3-bis(palmitoyloxy)-(2RS)-propyl]-[R]-cysteinyl-[S]-seryl-[S]-lysyl-[S]-lysyl-[S]-lysyl-[S]-lysine-[R]-cysteinyl-[S]-lysyl-biotin

Conditions
ConditionsYield
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
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