71989-33-8

Basic information

• Product Name: FMOC-O-tert-Butyl-L-serine
• Synonyms: N-(9-FLUORENYLMETHOXYCARBONYL)-2-TERT-BUTYL-L-SERINE;NALPHA-9-Fluorenylmethoxycarbonyl-O-tert-butyl-L-serine;FMOC-O-TERT-BUTYL-L-SERINE (FMOC-L-SER(TBU)-OH);O-tert-Butyl-N-Fmoc-L-serine;9-fluorenylmethoxycarbonyl-O-tert-butyl-L-serine;N-Fmoc-O-tert-Butyl-L-serine, Fmoc-O-tert-butyl-L-serine;N-FMOC-L-Ser (O-tert-Bu) OH;2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-[(2-methylpropan-2-yl)oxy]propanoic acid
• CAS NO: 71989-33-8
• Molecular Formula: C₂₂H₂₅NO₅
• Molecular Weight: 383.44
• EINECS: 276-260-6
• Product Categories: Fluorenes, Flurenones;Amino Acids;Serine [Ser, S];Fmoc-Amino Acids and Derivatives;Amino Acids (N-Protected);Biochemistry;Fmoc-Amino Acids;Fmoc-Amino acid series
• Mol File: 71989-33-8.mol
• Article Data: 16

Chemical Properties

• Melting Point: 130.5-135.5 °C(lit.)
• Boiling Point: 510.36°C (rough estimate)
• Flash Point: 303.7 °C
• Appearance: white to light yellow crystal powder
• Density: 1.2369 (rough estimate)
• Vapor Pressure: 3.16E-14mmHg at 25°C
• Refractive Index: 24 ° (C=1, AcOEt)
• Storage Temp.: 2-8°C
• PKA: 3.44±0.10(Predicted)
• BRN: 3632013
• CAS DataBase Reference: FMOC-O-tert-Butyl-L-serine(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-O-tert-Butyl-L-serine(71989-33-8)
• EPA Substance Registry System: FMOC-O-tert-Butyl-L-serine(71989-33-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36/37/39-27-26
• WGK Germany: 3
• Hazardous Substances Data: 71989-33-8(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

Fmoc-Ser(tBu)-OH is an N-terminal protected reagent used in the peptide synthesis. Some of the reported examples are:Total synthesis of an antibiotic, daptomycin, by cyclization via a chemoselective serine ligation.Preparation of MUC1, a T-cell helper peptide, using iterative pentafluorophenyl ester-mediated fragment condensations.Linear solid-phase peptide synthesis of ubiquitin and diubiquitin.

General Description

The product number for this product was previously 04-12-1033.To obtain a certificate of analysis (CoA) of a lot that begins with the letter “A”, please select the option in the right hand menu “Request a COA for Lot#s starting with A”.

InChI:InChI=1/C22H25NO5/c1-22(2,3)28-13-19(20(24)25)23-21(26)27-12-18-16-10-6-4-8-14(16)15-9-5-7-11-17(15)18/h4-11,18-19H,12-13H2,1-3H3,(H,23,26)(H,24,25)/p-1/t19-/m0/s1

Synthetic route

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

Conditions	Yield
With magnesium iodide In tetrahydrofuran at 120℃; for 1h; Inert atmosphere; Microwave irradiation; Sealed tube; chemoselective reaction;	98%
With aluminum (III) chloride In ethyl acetate Reflux;	86%

N-Fmoc-L-Ser(t-But)-OEt → Fmoc-Ser(tBu)-OH (71989-33-8)

Conditions	Yield
With aluminum (III) chloride In ethyl acetate Reflux;	84.8%

(S)-3-tert-Butoxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid tert-butyl ester (129460-16-8) → Fmoc-Ser(tBu)-OH (71989-33-8) + N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine (73724-45-5)

Conditions	Yield
With silica gel In toluene for 1.25h; Heating;	A 76% B 8%

(S)-O-tert-butylserine (18822-58-7) + 9-fluorenylmethyl N-succinimidyl carbonate (102774-86-7) → Fmoc-Ser(tBu)-OH (71989-33-8)

Conditions	Yield
With triethylamine In water; acetonitrile for 1h;	75%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + O-tert-Butyl-L-serine Methyl Ester p-Toluenesulfonate (132776-33-1) → Fmoc-Ser(tBu)-OH (71989-33-8)

Conditions	Yield
With sodium carbonate 1.) H2O, r.t., 24 h; 2.) p-dioxane, 0 deg C to r.t., 24 h; other reagent (1. step): NaOH; Yield given. Multistep reaction;

Fmoc-Ser(but)-O-Pha (146346-72-7) → Fmoc-Ser(tBu)-OH (71989-33-8)

Conditions	Yield
With acetic acid; zinc Yield given;
With magnesium; acetic acid In methanol; N,N-dimethyl-formamide at 20℃; for 75h;

Fmoc-Ser(But)-OSi(CH3)3 → Fmoc-Ser(tBu)-OH (71989-33-8)

Conditions	Yield
With water In 1,4-dioxane; ethyl acetate Ambient temperature; Yield given;

(S)-O-tert-butylserine (18822-58-7) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → Fmoc-Ser(tBu)-OH (71989-33-8)

(S)-3-tert-Butoxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid tert-butyl ester (129460-16-8) → Fmoc-Ser(tBu)-OH (71989-33-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: i-Pr2NEt / dioxane / 1 h / Heating 2: H2O / dioxane; ethyl acetate / Ambient temperature View Scheme

N-Fmoc serine phenacyl ester (125760-26-1) → Fmoc-Ser(tBu)-OH (71989-33-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 240 h 2: zinc, acetic acid View Scheme

N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine (73724-45-5) → Fmoc-Ser(tBu)-OH (71989-33-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: diisopropylethylamine / ethyl acetate 2: 240 h 3: zinc, acetic acid View Scheme

Fmoc-O-t-butyl-L-serine-N-hydroxysuccinimide ester → Fmoc-Ser(tBu)-OH (71989-33-8)

Conditions	Yield
With benzotriazol-1-ol; 17O-water In tetrahydrofuran at 20℃; for 96 - 120h;

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + C7H15NO3*ClH (247595-36-4) → Fmoc-Ser(tBu)-OH (71989-33-8)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 2h;

N-[(9-fluorenylmethoxy)carbonyl]-L-serine methyl ester (82911-78-2) → Fmoc-Ser(tBu)-OH (71989-33-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: perchloric acid / 1 h / 20 °C / Cooling with ice 2: aluminum (III) chloride / ethyl acetate / Reflux View Scheme

C104H160N10O10S (1258442-44-2) + Fmoc-Ser(tBu)-OH (71989-33-8) → C126H183N11O14S (1258442-36-2)

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%

C42H37ClNO6Pol + C29H31NO5 + N-Cbz-L-Phe (1161-13-3) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (35661-39-3) + O-benzyl-N-Fmoc-L-serine (122889-11-6, 83792-48-7) + Fmoc-Pro-OH (71989-31-6) + Fmoc-Ser(tBu)-OH (71989-33-8) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine (71989-28-1) + Nα-FMOC-Nω-L-tosylarginine (139090-50-9, 83792-47-6) + N-(((9H-fluoren-9-yl)methoxy)carbonyl)-O-(tert-butyldimethylsilyl)-L-threonine (146346-82-9) + N-alpha-(9-fluorenylmethyloxycarbonyl)-L-aspartic acid beta-allyl ester (146982-24-3) → Z-Phe-Ala-Thr(TBS)-Met-Arg(Tos)-Tyr(Pen)-Pro-Ser(tBu)-Asp(OAll)-Ser(Bzl)-Asp(OtBu)-OH (1240360-55-7)

Conditions

Yield

Stage #1: C42H37ClNO6Pol With morpholine Automated synthesizer; solid phase reaction; Stage #2: O-benzyl-N-Fmoc-L-serine With O‑(6‑chlorobezotriazol‑1‑yl)‑N,N,N,N‑tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; 6-chloro-1-hydroxybenzotriazole In 1-methyl-pyrrolidin-2-one Automated synthesizer; solid phase reaction; Stage #3: C29H31NO5; N-Cbz-L-Phe; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; Fmoc-Pro-OH; Fmoc-Ser(tBu)-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine; Nα-FMOC-Nω-L-tosylarginine; N-(((9H-fluoren-9-yl)methoxy)carbonyl)-O-(tert-butyldimethylsilyl)-L-threonine; N-alpha-(9-fluorenylmethyloxycarbonyl)-L-aspartic acid beta-allyl ester Further stages;

100%

...Expand

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-Ser(tBu)-OH (71989-33-8) + Fmoc-(tBu)Asp-OH (71989-14-5) + Fmoc-Arg(Pbf)-OH (119831-72-0) + 2-(6-isocyanatohexylaminocarbonylamino)-6-methyl-4-pyrimidinone (320393-85-9) → C36H58N16O15 (1262277-03-1)

Conditions	Yield
Stage #1: Fmoc-Ser(tBu)-OH With dmap; benzotriazol-1-ol; diisopropyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 21℃; for 24h; Stage #2: With piperidine In N,N-dimethyl-formamide at 21℃; for 0.0833333h; Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-(tBu)Asp-OH; Fmoc-Arg(Pbf)-OH; 2-(6-isocyanatohexylaminocarbonylamino)-6-methyl-4-pyrimidinone Further stages;	100%

1-decanoic acid (334-48-5) + Nα-Fmoc-Nδ-(acetyl)-Nδ-(benzoyloxy)-L-ornithine + Fmoc-Ser(tBu)-OH (71989-33-8) + Fmoc-Orn(Boc)-OH (109425-55-0) → DA-Lys-Ser-Orn(Ac-OH)-OH

Conditions	Yield
Stage #1: Nα-Fmoc-Nδ-(acetyl)-Nδ-(benzoyloxy)-L-ornithine With N-ethyl-N,N-diisopropylamine In dichloromethane for 1h; Stage #2: 1-decanoic acid; Fmoc-Ser(tBu)-OH; Fmoc-Orn(Boc)-OH With piperidine In N,N-dimethyl-formamide Further stages;	100%

Fmoc-Ser(tBu)-OH (71989-33-8) + tert-butyl 2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)acetate (518044-31-0) → FmocNH-Ser(OtBu)-O(CH2CH2O)3CH2C(O)OtBu

Conditions	Yield
With dmap In dichloromethane at 20℃; for 4h; Inert atmosphere;	100%

Fmoc-Ser(tBu)-OH (71989-33-8) → N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine (73724-45-5)

Conditions	Yield
With triethylsilane; trifluoroacetic acid In dichloromethane for 0.25h; Ambient temperature;	99%
With trifluoroacetic acid at 0℃; Kinetics; Activation energy; Thermodynamic data; Further Variations:; Temperatures; Reagents;
With trifluoroacetic acid In dichloromethane at 20℃; for 2h; Inert atmosphere;	84 mg
With hydrogenchloride In water at 20℃; for 4h; Solvent; Time;
With trifluoroacetic acid In water at 20℃; for 4h;	4.96 g

glycine ethyl ester hydrochloride (623-33-6) + Fmoc-Ser(tBu)-OH (71989-33-8) → N-fluorenylmethoxycarbonyl-O-tert-butyl-L-seryl-glycine ethyl ester (1028450-88-5)

Conditions	Yield
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	99%

Fmoc-Ser(tBu)-OH (71989-33-8) + (S)-allyl 2-amino-6-((tert-butoxycarbonyl)amino)hexanoate (220331-35-1) → Fmoc-Ser(tBu)-Lys(Boc)-O-allyl

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃;	99%
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 0 - 20℃; for 15h;	90%

Fmoc-Ser(tBu)-OH (71989-33-8) + O-t-butyl serine benzyl ester (113247-75-9) → C36H44N2O7

Conditions	Yield
With 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 2h;	99%

C7H14NO3Pol + N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (35661-39-3) + N-Fmoc L-Phe (35661-40-6) + Fmoc-Ser(tBu)-OH (71989-33-8) + Fmoc-Glu(OtBu)-OH (71989-18-9) → butyrylcholinesterase nonapeptide

Conditions

Yield

Stage #1: C7H14NO3Pol; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine With dicyclohexyl-carbodiimide; ethyl cyanoglyoxylate-2-oxime In dichloromethane at 20℃; for 1h; Stage #2: With piperidine In N,N-dimethyl-formamide at 20℃; for 0.3h; Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; N-Fmoc L-Phe; Fmoc-Ser(tBu)-OH; Fmoc-Glu(OtBu)-OH Further stages;

99%

Fmoc-Ser(tBu)-OH (71989-33-8) + Dimethyl-(3-methyl-2-butenyl)-sulfonium tetrafluoroborate → C27H33NO5

Conditions	Yield
Stage #1: Fmoc-Ser(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;	99%

Fmoc-Ser(tBu)-OH (71989-33-8) + 2,4,6-trivinylcyclotriboroxane*pyridine complex → (L)-N-Fmoc-O-tert-butyl serine vinyl ester

Conditions	Yield
With N,N'-diethylurea; copper(II) bis(trifluoromethanesulfonate); triethylamine In tetrahydrofuran at 50℃; for 16h; Chan-Lam Coupling;	99%

2-(2-(2-(3,4,5-tris(isononyloxy)benzamido)ethoxy)ethoxy)benzylalcohol + Fmoc-Ser(tBu)-OH (71989-33-8) → C67H98N2O11

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 5℃; for 5h;	99%

Fmoc-Ser(tBu)-OH (71989-33-8) → FMOC-Ser(t-Bu)-F (130858-98-9)

Conditions	Yield
With pyridine; trifluoro-[1,3,5]triazine In dichloromethane at 20℃; for 15h;	98%
With pyridine; trifluoro-[1,3,5]triazine In dichloromethane at 20℃;	97%
With pyridine; trifluoro-[1,3,5]triazine In dichloromethane for 1.5h; Ambient temperature;	72.7%
With diethylamino-sulfur trifluoride In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;

methyl (2S)-2-amino-6-{[(benzyloxy)carbonyl]amino}hexanoate hydrochloride (27894-50-4) + Fmoc-Ser(tBu)-OH (71989-33-8) → Fmoc-Ser(tBu)-Lys(Z)-OMe (442663-72-1)

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; pH=8 - 9;	98%

Fmoc-Ser(tBu)-OH (71989-33-8) + phenylmethanethiol (100-53-8) → N-(fluoren-9-ylmethoxycarbonyl)-O-(tert-butyl)-L-serine S-benzyl ester (1259301-22-8)

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 120h; Inert atmosphere;	98%
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 18h;	91%

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + N-Fmoc L-Phe (35661-40-6) + Fmoc-Ser(tBu)-OH (71989-33-8) + N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine (103213-32-7) + Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine → H2N-L-Cys(Trt)-L-Arg(Pbf)-L-Cys(Trt)-L-Phe-L-Ser(tBu)-Gly-OH trifluoroacetate

Conditions	Yield
Stage #1: N-(fluoren-9-ylmethoxycarbonyl)glycine With N-ethyl-N,N-diisopropylamine In dichloromethane for 0.916667h; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.333333h; Stage #3: N-Fmoc L-Phe; Fmoc-Ser(tBu)-OH; N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine Further stages;	98%

Fmoc-Val-OH (68858-20-8) + N-Fmoc L-Phe (35661-40-6) + Fmoc-Ser(tBu)-OH (71989-33-8) + Fmoc-Ile-OH (71989-23-6) + N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine (103213-32-7) → H2N-L-Val-L-Ser(tBu)-L-Phe-L-Cys(Trt)-L-Ile-L-Cys(Trt)-OH trifluoroacetate

Conditions	Yield
Stage #1: N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine With N-ethyl-N,N-diisopropylamine In dichloromethane for 0.916667h; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.333333h; Stage #3: Fmoc-Val-OH; N-Fmoc L-Phe; Fmoc-Ser(tBu)-OH; Fmoc-Ile-OH; N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine Further stages;	98%

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-Ser(tBu)-OH (71989-33-8) + Fmoc-Tyr(tBu)-OH (71989-38-3) + Fmoc-D(*)-OH → C29H37N7O11

Conditions	Yield
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%

C35H34N4O5 + Fmoc-Ser(tBu)-OH (71989-33-8) + Fmoc-(tBu)Asp-OH (71989-14-5) + acetic anhydride (108-24-7) + Fmoc-Ile-OH (71989-23-6) + Fmoc-Thr(tBu)-OH (71989-35-0) → C51H79N9O11

Conditions	Yield
Stage #1: Fmoc-Ile-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; Fmoc-Ser(tBu)-OH; Fmoc-(tBu)Asp-OH; acetic anhydride; Fmoc-Thr(tBu)-OH Further stages;	98%

fmoc-Lys(Boc)-Wang resin + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (35661-39-3) + Fmoc-Pro-OH (71989-31-6) + Fmoc-Ser(tBu)-OH (71989-33-8) + Fmoc-Tyr(tBu)-OH (71989-38-3) + Fmoc-Lys(tert-butoxycarbonyl) (71989-26-9) + Fmoc-Thr(tBu)-OH (71989-35-0) + (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)

Conditions

Yield

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%

...Expand

tert-butyl L-alaninate hydrochloride (13404-22-3) + Fmoc-Ser(tBu)-OH (71989-33-8) → O-tert-Butyl-N-(9-fluorenylmethoxycarbonyl)-L-seryl-L-alanin-tert-butylester (120173-65-1)

Conditions	Yield
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine In dichloromethane for 24h;	97%

C12H19NO2 (1083074-09-2) + Fmoc-Ser(tBu)-OH (71989-33-8) → C34H42N2O6 (1083074-18-3)

Conditions	Yield
With N'-methyl polystyrene; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Inert atmosphere;	97%

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + C21H43N2O4PolS + Fmoc-Arg(pbf)-OH (1364408-78-5) + Fmoc-Ser(tBu)-OH (71989-33-8) + Fmoc-(tBu)Asp-OH (71989-14-5) → C40H74N10O13S

Conditions	Yield
Stage #1: C21H43N2O4PolS; Fmoc-Ser(tBu)-OH With 1-hydroxy-7-aza-benzotriazole; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 1h; 2-chlorotrityl chloride resin; Stage #2: With piperidine In N,N-dimethyl-formamide Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Arg(pbf)-OH; Fmoc-(tBu)Asp-OH Further stages;	97%

Fmoc-Ser(tBu)-OH (71989-33-8) + N(ε)-benzoyloxycarbonyl-L-lysine tert-butyl ester hydrochloride (5978-22-3) → tert-butyl-N2-(N-(((9H-fluoren-9-yl)methoxy)carbonyl)-O-(tert-butyl)-L-seryl)-N6-((benzyloxy)carbonyl)-L-lysinate

Conditions	Yield
With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide for 0.0833333h; Reagent/catalyst; Solvent; Flow reactor;	97%

methyl (L)-leucinate hydrochloride (7517-19-3) + Fmoc-Ser(tBu)-OH (71989-33-8) → N-(9-fluorenyl)methoxycarbonyl-(O-tert-butyl)-L-seryl-L-leucine methyl ester

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; pentafluorophenyl 4-nitrobenzenesulfonate; 1-hydroxybenzotriazol-hydrate In N,N-dimethyl-formamide at 20℃; for 1h;	96%

hexan-1-amine (111-26-2) + Fmoc-Ser(tBu)-OH (71989-33-8) → Fmoc-O-tert-butyl-L-serine hexylamide (918130-60-6)

Conditions	Yield
With benzotriazol-1-ol; diisopropyl-carbodiimide In dichloromethane at 25℃; for 3h;	96%

(9H-fluoren-9-yl)methyl (3-methyl-1-(1H-tetrazol-5-yl) butyl)-carbamate (954147-19-4) + Fmoc-Ser(tBu)-OH (71989-33-8) + Fmoc-Lys(tert-butoxycarbonyl) (71989-26-9) + Fmoc-L-Gln(Trt)-OH (132327-80-1) → C29H47N11O7

Conditions	Yield
Multistep reaction.;	96%

Fmoc-Ser(tBu)-OH (71989-33-8) + (S)-allyl 2-amino-3-(4-(tert-butoxy)phenyl)propanoate (267001-22-9) → Fmoc-Ser(tBu)-Tyr(tBu)-Oallyl (937077-24-2)

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 45℃;	96%

Upstream product

• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 247595-36-4 C₇H₁₅NO₃*ClH 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 132776-33-1 O-tert-Butyl-L-serine Methyl Ester p-Toluenesulfonate 
• 18822-58-7 (S)-O-tert-butylserine 
• 102774-86-7 9-fluorenylmethyl N-succinimidyl carbonate 
• 17083-26-0 O-tert-butyl-L-serine methyl ester 
• 158000-21-6 Fmoc-O-t-butyl-L-serine-N-hydroxysuccinimide ester 
• 73724-45-5 N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine 
• 125760-26-1 N-Fmoc serine phenacyl ester 
• 129460-16-8 (S)-3-tert-Butoxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid tert-butyl ester 
• 146346-72-7 Fmoc-Ser(bu^t)-O-Pha 
• 82911-78-2 N-[(9-fluorenylmethoxy)carbonyl]-L-serine methyl ester 

Downstream Products

• 71989-34-9 Fmoc-Ser(t-Bu)-ONp 
• 113534-37-5 Fmoc-Ser(tBu)-OTDO 
• 126771-45-7 (S)-3-tert-Butoxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 4-(2,4-dichloro-phenoxycarbonylmethoxy)-benzyl ester 
• 120792-11-2 O-tert-Butyl-N-(9-fluorenylmethoxycarbonyl)-L-seryl-O-tert-butyl-L-threonyl-N^ε-(tert-butoxycarbonyl)-L-lysyl-N^ε-(tert-butoxycarbonyl)-L-lysyl-O-tert-butyl-L-threonin-benzylester 
• 120792-12-3 O-tert-Butyl-N-(9-fluorenylmethoxycarbonyl)-L-seryl-O-tert-butyl-L-seryl-O-tert-butyl-L-threonyl-N^ε-(tert-butoxycarbonyl)-L-lysyl-N^ε-(tert-butoxycarbonyl)-L-lysyl-O-tert-butyl-L-threonin-benzylester 
• 120792-13-4 O-tert-Butyl-N-(9-fluorenylmethoxycarbonyl)-L-seryl-O-tert-butyl-L-seryl-O-tert-butyl-L-seryl-O-tert-butyl-L-threonyl-N^ε-(tert-butoxycarbonyl)-L-lysyl-N^ε-(tert-butoxycarbonyl)-L-lysyl-O-tert-butyl-L-threonin-benzylester 
• 73724-45-5 N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine 
• 176842-74-3 N-(9-fluorenylmethoxycarbonyl)-O-(tert-butyl)-L-seryl-L-proline benzyl ester 
• 33515-09-2 L-pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosylglycyl-L-leucyl-L-arginyl-L-prolylglycinamide 
• 280112-67-6 Asp-Ser-Phe-Gly-OCH₂CH(OH)CH₂OH 
• 442663-72-1 Fmoc-Ser(tBu)-Lys(Z)-OMe 

Relevant articles and documents

Method for preparing Fmoc-Ser (tBu)-OH

The invention relates to a method for preparing Fmoc-Ser (tBu)-OH, and belongs to the technical field of medical intermediate chemical engineering. The technical problem to be solved by the inventionis to provide a method for preparing Fmoc-Ser (tBu)-OH. The method comprises the following steps: a, enabling Ser-OR. HCl to react with Fmoc-OSu, so as to obtain an Fmoc-Ser-OR solid; b, mixing the Fmoc-Ser-OR solid, tert-butyl acetate, perchloric acid and tert-butyl alcohol, reacting at 15-40 DEG C, regulating the pH value to 5-6, separating out a solid, filtering, washing and drying to obtain anFmoc-Ser (tBu)-OR solid; and c, hydrolysis: carrying out hydrolysis on the Fmoc-Ser (tBu)-ORsolid to obtain an Fmoc-Ser (tBu)-OH product. According to the method, the Fmoc group is introduced firstly, the racemization risk in the saponification process can be reduced, tert-butyl acetate, perchloric acid, tert-butyl alcohol and hydroxyl in Fmoc-Ser-OR are adopted for reaction when tert-butyl is introduced, operation is easy and controllable, safety is good, the obtained product is high in chiral purity and low in cost, the production steps can be effectively shortened, and the production efficiency and yield are improved; the method is suitable for modern industrial production.

MgI2-Mediated Chemoselective Cleavage of Protecting Groups: An Alternative to Conventional Deprotection Methodologies

The scope of MgI2 as a valuable tool for quantitative and mild chemoselective cleavage of protecting groups is described here. This novel synthetic approach expands the use of protecting groups, widens the concept of orthogonality in synthetic processes, and offers a facile opportunity to release compounds from solid supports. Amazing MgI2: Protecting groups have had a tremendous positive impact on the art of biomolecule synthesis. In a context in which the use of attractive protecting groups is often limited by harsh deprotection conditions and low chemoselective flexibility, MgI2 offers, by the execution of a very simple protocol, a fresh vision with extensive perspectives.

NOVEL PEPTIDES DERIVED FROM NCAM (FGLs)

The present invention relates to novel compounds comprising at most 13 contiguous amino acid residues derived from the fibronectin type 3,I1 module of neural cell adhesion molecule (NCAM), or a variant or fragment thereof, capable of interacting with an FGFR and thereby the compounds are capable of inducing differentiation, modulating proliferation, stimulate regeneration, neuronal plasticity and/or survival of cells. Further, the present invention relates to the use of said compounds for production of a medicament for treatment of conditions and diseases, wherein NCAM and/or FGFR play a prominent role.