18822-58-7

Basic information

• Product Name: H-SER(TBU)-OH
• Synonyms: Ser(tBu);L-Ser(tBu)-OH;O-tert-Butyl-L-serine≥ 99% (HPLC, Chiral purity);L-SERINE T-BUTYL ETHER;H-SER(BUT)-OH;H-SER(TBU)-OH;O-T-BUTYL-L-SERINE;O-TERT-BUTYL-L-SERINE
• CAS NO: 18822-58-7
• Molecular Formula: C₇H₁₅NO₃
• Molecular Weight: 161.2
• EINECS: 1533716-785-6
• Product Categories: Amino Acids;Serine [Ser, S];Amino Acids and Derivatives;Peptide Synthesis;A - HPeptide Synthesis;Amino Acid Derivatives;Amino Acids;Modified Amino Acids;Serine
• Mol File: 18822-58-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: ~220 °C (dec.)
• Boiling Point: 266 °C at 760 mmHg
• Flash Point: 114.6 °C
• Appearance: White/Powder
• Density: 1.08 g/cm³
• Vapor Pressure: 0.00257mmHg at 25°C
• Refractive Index: 1.465
• Storage Temp.: 2-8°C
• PKA: 2.11±0.10(Predicted)
• Water Solubility: Soluble in water.
• CAS DataBase Reference: H-SER(TBU)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: H-SER(TBU)-OH(18822-58-7)
• EPA Substance Registry System: H-SER(TBU)-OH(18822-58-7)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 18822-58-7(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

O-tert-Butyl-L-serine tert-butyl ester hydrochloride is a protected L-serine used in peptide synthesis, e.g. synthesis of glycopeptides and lipopeptides and preparation of amino-phospholipids. O-tert-Butyl-L-serine (Ser(TBU-OH), a serine hydroxyl protected amino acid, is used in SPPS such as the synthesis of tailed cyclic RGD peptides to prevent glutarimide formation.

InChI:InChI=1/C7H15NO3/c1-7(2,3)11-4-5(8)6(9)10/h5H,4,8H2,1-3H3,(H,9,10)/t5-/m0/s1

Upstream product

• 71989-33-8 Fmoc-Ser(tBu)-OH 
• 1872-59-9 (S)-methyl 2-(((benzyloxy)carbonyl)amino)-3-(tert-butoxy)propanoate 
• 115-11-7 isobutene 
• 20700-93-0 Z-Ser(O-t-Bu)-OBn 
• 47634-33-3 Bpoc-Ser(Bu^t)-OH 
• 6169-34-2 N-Benzyloxycarbonyl-β-O-tert.butyl-L-serin-<4-nitro-benzylester> 
• 1676-75-1 N-benzyloxycarbonyl-O-t-butyl-L-serine 

Downstream Products

• 1209480-93-2 NVOC-Ser(tBu)-OH 
• 1221251-52-0 C₅₈H₇₄N₆O₁₀ 
• 1221251-49-5 C₅₅H₆₈N₆O₁₀ 
• 1221251-44-0 Ac-W(Boc)-S(t-Bu)-N(Trt)-L 
• 1250965-47-9 C₁₈H₂₆ClN₃O₆ 
• 127959-11-9 H-Tyr-Ser-Pro-Thr-Ser-Pro-Ser-Tyr-OH 
• 71989-33-8 Fmoc-Ser(tBu)-OH 
• 47555-19-1 (S)-3-tert-Butoxy-2-[1-(3,5-dimethoxy-phenyl)-1-methyl-ethoxycarbonylamino]-propionic acid 
• 160422-21-9 2-(4-nitrophenylsulfonyl)ethoxycarbonyl-Ser(t-Bu)-OH (Nsc-Ser(t-Bu)-OH) 
• 18783-53-4 O-tert-Butyl-D-serine 

Relevant articles and documents

Compound of benzyl structure and application of compound

The invention discloses a compound of a benzyl structure and application of the compound. The compound of the benzyl structure comprises hydroxyl, amino, substituted amino and active groups, and can be used as an amino acid or peptide C-end protection reagent. A peptide synthesis reaction using the protection carrier is rapid in reaction speed and high in reagent utilization rate in an appropriatesolvent system; effective purification can be implemented through simple liquid-liquid extraction separation in post-processing, and a product of high purity can be finally obtained; and in the synthesis process, the dissolution degree is slightly changed, the operation process is good in universality, and a universal production method can be developed.

Selective Deprotection of the Nα-tert-Butyloxycarbonyl Group in Solid Phase Peptide Synthesis with Chlorotrimethylsilane and Phenol

The repetitive deprotection of the Nα-tert-butyloxycarbonyl group during solid phase peptide synthesis was found to be efficient and quantitative by use of a mild new reagent containing 1 M chlorotrimethylsiane and 1 M phenol in dichloromethane.Kinetic studies showed that the half-life for the reaction at 22 deg C with Boc-Val-resin was 17.5 min, a 40-fold increase over the rate in the absence of phenol.The reaction is not due to the presence of HCl in the reagent.The selectivity between the removal at the Nα-tert-butyloxycarbonyl group and benzylic esters, ethers, and carbonate side chain protecting groups was >1E5 and relative to the anchoring benzyl ester bond to the resin support it was 6E3.This is a marked improvement over the selectivity of the conventional 50percent trifluoroacetic acid in CH2Cl2 deprotecting agent and significantly reduces the accumulated byproducts resulting from losses of benzylic groups.The cleavage of the tert-butyl urethane was first order in Me3SiCl and second order in C6H5OH.The preferred reagent is 1 M Me3SiCl-3 M C6H5OH-CH2Cl2 and the deprotection time is 20 min (t1/2 = 1.8 min for Boc-Val-OCH2-resin).Evidence for the mechanism of the reaction was deduced.Several peptides, including Leu-enkephalin, -angiotensin II, and glucagon were successfully synthesized in high yields and excellent purity by the stepwise solid phase method using this new reagent.