132388-59-1

Basic information

• Product Name: Fmoc-N-trityl-L-asparagine
• Synonyms: N-ALPHA-FMOC-N-GAMMA-TRITYL-L-ASPARAGINE;FMOC-ASPARAGINE(TRT);FMOC-ASN(XAN)-OH;FMOC-ASN(TRT)-OH;FMOC-ASN(TRT);FMOC-L-ASN(TRITYL);FMOC-L-ASN(TRT)-OH;FMOC-L-ASPARGINE(TRITYL)
• CAS NO: 132388-59-1
• Molecular Formula: C₃₈H₃₂N₂O₅
• Molecular Weight: 596.67
• Product Categories: Protected Amino Acids;Fluorenes, Flurenones;Amino Acids;Asparagine [Asn, N];Fmoc-Amino Acids and Derivatives;Amino Acids (N-Protected);Biochemistry;Fmoc-Amino Acids;Fmoc-Amino acid series
• Mol File: 132388-59-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: 201-204 °C(lit.)
• Boiling Point: 858.1 °C at 760 mmHg
• Flash Point: 472.8 °C
• Appearance: White to off white free flowing powder
• Density: 1.271 g/cm³
• Vapor Pressure: 2.26E-31mmHg at 25°C
• Refractive Index: -19 ° (C=1, DMF)
• Storage Temp.: 2-8°C
• Solubility: <0.00005g/l
• PKA: 3.79±0.10(Predicted)
• BRN: 4343823
• CAS DataBase Reference: Fmoc-N-trityl-L-asparagine(CAS DataBase Reference)
• NIST Chemistry Reference: Fmoc-N-trityl-L-asparagine(132388-59-1)
• EPA Substance Registry System: Fmoc-N-trityl-L-asparagine(132388-59-1)

Safety Data

• Statements: 53
• Safety Statements: 24/25-61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 2
• F: 3-10
• HazardClass: IRRITANT
• Hazardous Substances Data: 132388-59-1(Hazardous Substances Data)

Usage

Chemical Properties

white crystal powde

Uses

Fmoc-Asn(Trt)-OH, is an amino acid derivative used in chemical synthesis and peptide chemistry.

InChI:InChI=1/C38H32N2O5/c41-35(40-38(26-14-4-1-5-15-26,27-16-6-2-7-17-27)28-18-8-3-9-19-28)24-34(36(42)43)39-37(44)45-25-33-31-22-12-10-20-29(31)30-21-11-13-23-32(30)33/h1-23,33-34H,24-25H2,(H,39,44)(H,40,41)(H,42,43)/p-1/t34-/m0/s1

Synthetic route

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + (S)-2-Amino-N-trityl-succinamic acid (132388-58-0) → L-Asn(Trt) (132388-59-1)

Fmoc-Asn(TrT)-F → L-Asn(Trt) (132388-59-1)

Conditions	Yield
With water In N,N-dimethyl-formamide for 24h; Product distribution; Ambient temperature; effect of water content on stability of various Fmoc-amino acid fluorides;

triphenylmethyl alcohol (76-84-6) → L-Asn(Trt) (132388-59-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / acetic anhydride, conc.H2SO4 / acetic acid / 1.25 h / 60 °C View Scheme
Multi-step reaction with 3 steps 1: acetic anhydride, conc.H2SO4 / acetic acid / 1 h / 50 °C 2: H2 / Pd-C View Scheme

N-benzyloxycarbonyl-N'-trityl-L-asparagine (132388-57-9) → L-Asn(Trt) (132388-59-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2 / Pd-C View Scheme

triphenylmethyl alcohol (76-84-6) + Fmoc-Asn-OH (71989-16-7) + 1,2-dichloro-ethane (107-06-2) → L-Asn(Trt) (132388-59-1)

Conditions	Yield
With sulfuric acid; acetic anhydride In tetrahydrofuran; methanol; di-isopropyl ether; water; acetic acid; ethyl acetate

aqueous potassium bisulfate + H-Asn(Trt)-OH.0.5 H2 O + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → L-Asn(Trt) (132388-59-1)

Conditions	Yield
With triethylamine In tetrahydrofuran; di-isopropyl ether; water; ethyl acetate

Fmoc-Asn(Trt)-OBt → L-Asn(Trt) (132388-59-1) + benzotriazol-1-ol (2592-95-2)

Conditions	Yield
With water for 6h; Kinetics;

C119H188N12O14S (1258442-46-4) + L-Asn(Trt) (132388-59-1) → C157H218N14O18S (1258442-38-4)

Conditions	Yield
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%

(4-(hydroxymethyl)phenyl)diphenylphosphine oxide (5068-20-2) + L-Asn(Trt) (132388-59-1) → C57H47N2O6P

Conditions	Yield
Stage #1: (4-(hydroxymethyl)phenyl)diphenylphosphine oxide; L-Asn(Trt) 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%

L-Asn(Trt) (132388-59-1) + methyl iodide (74-88-4) → methyl (S)-2-((9H-fluoren-9-yl)methoxycarbonylamino)-4-oxo-4-(tritylamino)butanoate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 1h;	99%

L-Asn(Trt) (132388-59-1) + D-Asn(Trt)-OBn → Fmoc-L-Asn(Trt)-D-Asn(Trt)-OBn

Conditions	Yield
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 25℃;	98%
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride	98%

Fmoc-Pro-OH (71989-31-6) + Fmoc-(tBu)Asp-OH (71989-14-5) + Fmoc-Lys(tert-butoxycarbonyl) (71989-26-9) + L-Asn(Trt) (132388-59-1) + Fmoc-(S)-2-aminohexanoic acid (77284-32-3) + N-(9-fluorenylmethoxycarbonyl)-D-valine (84624-17-9) → C58H82N8O12

Conditions

Yield

Stage #1: Fmoc-(tBu)Asp-OH With O-(1H-6-chlorobenzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.833333h; 2-chlorotrityl resin; Automated synthesizer; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.0833333h; 2-chlorotrityl resin; Automated synthesizer; Stage #3: Fmoc-Pro-OH; Fmoc-Lys(tert-butoxycarbonyl); L-Asn(Trt); Fmoc-(S)-2-aminohexanoic acid; N-(9-fluorenylmethoxycarbonyl)-D-valine Further stages;

97%

L-Asn(Trt) (132388-59-1) + tert-butyl 4-aminobutanoate hydrochloride → Fmoc-Asn(Trt)-GABA-OtBu

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In dichloromethane Inert atmosphere;	97%

L-Asn(Trt) (132388-59-1) + tert-butylamine (75-64-9) → Fmoc-Asn(Trt)-NHtBu (1370293-55-2)

Conditions	Yield
With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -20 - -18℃; for 2h;	96%

L-Asn(Trt) (132388-59-1) + 4-methoxycarbonyl aniline (619-45-4) → methyl (S)-4-(2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-oxo-4-(tritylamino)butanamido)benzoate

Conditions	Yield
With triethylamine; trichlorophosphate In dichloromethane at 0℃; for 2h;	96%
With triethylamine; trichlorophosphate In dichloromethane at 0℃; for 2h; Inert atmosphere;	13.97 g

HCl*H-Ser(tBu)-Phe-Arg(Pbf)-Tyr(tBu)-OKb, Kb=2,4-didocosyloxybenzyl + L-Asn(Trt) (132388-59-1) → HCl*H-Asn(Trt)-Ser(tBu)-Phe-Arg(Pbf)-Tyr(tBu)-Okb, Kb=2,4-didocosyloxybenzyl

Conditions

Yield

Stage #1: HCl*H-Ser(tBu)-Phe-Arg(Pbf)-Tyr(tBu)-OKb, Kb=2,4-didocosyloxybenzyl; L-Asn(Trt) With 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; ethyl cyanoglyoxylate-2-oxime In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: With piperidine; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #3: With hydrogenchloride In tetrahydrofuran; water; N,N-dimethyl-formamide pH=Ca. 6;

95.4%

L-Asn(Trt) (132388-59-1) + tert-butyldimethylsilyl chloride (18162-48-6) → (S)-Nα-(Fluoren-9-ylmethoxycarbonyl)-Nγ-tritylasparagine tert-butyldimethylsilyl ester (313944-83-1)

Conditions	Yield
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 1.41667h; Esterification;	95%

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (35661-39-3) + C20H18NO4Pol + L-Asn(Trt) (132388-59-1) + 2-(9H-fluoren-9-ylmethoxycarbonylamino)-pent-4-enoic acid (146549-21-5) + N-(tert-butoxycarbonyl)-D-allylglycine (170899-08-8) + (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)pent-4-enoic acid (170642-28-1) → 2-[2-(2-{2-[2-(2-tert-butoxycarbonylamino-pent-4-enoylamino)-propionylamino]-pent-4-enoylamino}-pent-4-enoylamino)-3-(trityl-carbamoyl)-propionylamino]-pent-4-enoic acid methyl ester (936116-88-0)

Conditions

Yield

Stage #1: C20H18NO4Pol With piperidine In 1-methyl-pyrrolidin-2-one not specified; Stage #2: L-Asn(Trt) With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one not specified; Stage #3: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; 2-(9H-fluoren-9-ylmethoxycarbonylamino)-pent-4-enoic acid; N-(tert-butoxycarbonyl)-D-allylglycine; (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)pent-4-enoic acid Further stages;

95%

L-Asn(Trt) (132388-59-1) → (S)-2-Amino-N-trityl-succinamic acid (132388-58-0)

Conditions	Yield
With sodium azide In N,N-dimethyl-formamide at 50℃; for 12h;	95%

4-aminobenzenemethanol (623-04-1) + L-Asn(Trt) (132388-59-1) → 9H-fluorene-9-ylmethyl[(2S)-1-{[4-(hydroxymethyl)phenyl]amino}-1,4-dioxo-4-(tritylamino)butane-2-yl]carbamate

Conditions	Yield
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In tetrahydrofuran at 20℃;	93%
Stage #1: L-Asn(Trt) With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide for 0.5h; Stage #2: 4-aminobenzenemethanol With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 3h;	90%
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 dichloromethane; N,N-dimethyl-formamide
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 0 - 20℃; for 3.5h;
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In tetrahydrofuran at 20℃;	19.2 g

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-Pro-OH (71989-31-6) + Fmoc-(tBu)Asp-OH (71989-14-5) + Fmoc-Ile-OH (71989-23-6) + Fmoc-Lys(tert-butoxycarbonyl) (71989-26-9) + L-Asn(Trt) (132388-59-1) → C55H76N8O12

Conditions

Yield

Stage #1: Fmoc-(tBu)Asp-OH With O-(1H-6-chlorobenzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.833333h; 2-chlorotrityl resin; Automated synthesizer; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.0833333h; 2-chlorotrityl resin; Automated synthesizer; Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Pro-OH; Fmoc-Ile-OH; Fmoc-Lys(tert-butoxycarbonyl); L-Asn(Trt) Further stages;

93%

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + C42H38N4O9 + Fmoc-(tBu)Asp-OH (71989-14-5) + L-Asn(Trt) (132388-59-1) + Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine → C51H69N17O16

Conditions	Yield
Stage #1: Fmoc-(tBu)Asp-OH With N-ethyl-N,N-diisopropylamine In dichloromethane for 4h; Inert atmosphere; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.35h; Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; C42H38N4O9; L-Asn(Trt); Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine Further stages;	92%

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + HCl*H-Glu(OtBu)-OKb, Kb=2,4-didocosyloxybenzyl + N-Fmoc L-Phe (35661-40-6) + Fmoc-(tBu)Asp-OH (71989-14-5) + L-Asn(Trt) (132388-59-1) → HCl*H-Gly-Asn(Trt)-Gly-Asp(OtBu)-Phe-Glu(OtBu)-OKb, Kb=2,4-didocosyloxybenzyl

Conditions

Yield

Stage #1: HCl*H-Glu(OtBu)-OKb, Kb=2,4-didocosyloxybenzyl; N-Fmoc L-Phe With N-ethyl-N,N-diisopropylamine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: With piperidine; benzotriazol-1-ol; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-(tBu)Asp-OH; L-Asn(Trt) Further stages;

90.8%

Fmoc-Val-OH (68858-20-8) + Fmoc-Ser(tBu)-OH (71989-33-8) + Fmoc-Glu(OtBu)-OH (71989-18-9) + acetic anhydride (108-24-7) + L-Asn(Trt) (132388-59-1) → Ac-S(tBu)E(OtBu)VN(trt)-OH (1447762-81-3)

Conditions	Yield
Stage #1: L-Asn(Trt) With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3.25h; Stage #2: With piperidine In N,N-dimethyl-formamide Stage #3: Fmoc-Val-OH; Fmoc-Ser(tBu)-OH; Fmoc-Glu(OtBu)-OH; acetic anhydride Further stages;	90%

(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-6-(dimethylamino)hexanoic acid + Fmoc-O-methyl-L-serine (159610-93-2) + N-Fmoc L-Phe (35661-40-6) + L-Asn(Trt) (132388-59-1) + N-(9-fluorenylmethoxycarbonyl)-O-methyl-L-tyrosine (77128-72-4) → HO-Phe-Tyr(Me)-Ser(Me)-Asn(Trt)-Lys(Me)2-NH2

Conditions	Yield
Stage #1: (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-6-(dimethylamino)hexanoic acid With N-ethyl-N,N-diisopropylamine In dichloromethane for 4h; Stage #2: With piperidine In N,N-dimethyl-formamide; isopropyl alcohol Stage #3: Fmoc-O-methyl-L-serine; N-Fmoc L-Phe; L-Asn(Trt); N-(9-fluorenylmethoxycarbonyl)-O-methyl-L-tyrosine Further stages;	90%

Upstream product

• 76-84-6 triphenylmethyl alcohol 
• 71989-16-7 Fmoc-Asn-OH 
• 107-06-2 1,2-dichloro-ethane 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 132388-57-9 N-benzyloxycarbonyl-N'-trityl-L-asparagine 
• 132388-58-0 (S)-2-Amino-N-trityl-succinamic acid 

Downstream Products

• 433922-97-5 2-(9H-fluoren-9-ylmethoxycarbonylamino)-N-trityl-succinamic acid 1-{[tert-butoxycarbonyl-(2-tert-butoxycarbonyl-1-isopropylcarbamoyl-ethyl)-amino]-methyl}-4-methyl-2-(2,4,6-trimethyl-benzenesulfonylamino)-pentyl ester 
• 668985-59-9 Fmoc-L-Asn(Trt)-L-Dap(Boc-L-Leu-D-Ala-L-Chp)-OBn 
• 668985-72-6 Fmoc-L-Asn(Trt)-L-Dab(Boc-L-Leu-D-Ala-L-Chp)-OBn 

Relevant articles and documents

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