152548-66-8

Basic information

• Product Name: Fmoc-N-methyl-L-aspartic acid 4-tert-butyl ester
• Synonyms: N-ALPHA-FMOC-N-ALPHA-METHYL-L-ASPARTIC ACID BETA-T-BUTYL ESTER;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-N-ALPHA-METHYL-L-ASPARTIC ACID BETA-T BUTYL ESTER;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-N-ALPHA-METHYL-L-ASPARTIC ACID BETA-TERT-BUTYL ESTER;FMOC-L-MEASP(TBU)-OH;FMOC-MEASP(OTBU)-OH;FMOC-N-ME-ASPARTIC ACID(OTBU)-OH;FMOC-N-ME-ASP(OTBU)-OH;FMOC-N-METHYL-L-ASPARTIC ACID BETA-T-BUTYL ESTER
• CAS NO: 152548-66-8
• Molecular Formula: C₂₄H₂₇NO₆
• Molecular Weight: 425.47
• Product Categories: PROTECTED AMINO ACID & PEPTIDES;Aspartic acid [Asp, D];N-Methyl Amino Acids;Fmoc-Amino acid series;amino acids
• Mol File: 152548-66-8.mol
• Article Data: 2

Chemical Properties

• Melting Point: 135-140°C
• Boiling Point: 598.7 °C at 760 mmHg
• Flash Point: 315.9 °C
• Appearance: white to off-white crystalline powder
• Density: 1.237 g/cm³
• Vapor Pressure: 3.52E-15mmHg at 25°C
• Refractive Index: 1.574
• Storage Temp.: -15°C
• PKA: 3.59±0.23(Predicted)
• CAS DataBase Reference: Fmoc-N-methyl-L-aspartic acid 4-tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Fmoc-N-methyl-L-aspartic acid 4-tert-butyl ester(152548-66-8)
• EPA Substance Registry System: Fmoc-N-methyl-L-aspartic acid 4-tert-butyl ester(152548-66-8)

Safety Data

• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 152548-66-8(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white solid

Uses

Fmoc protected N-methyl amino acid suitable for solid phase peptide synthesis. N-methyl amino acids have been shown to improve proteolytic stability of peptides.

InChI:InChI=1/C24H27NO6/c1-24(2,3)31-21(26)13-20(22(27)28)25(4)23(29)30-14-19-17-11-7-5-9-15(17)16-10-6-8-12-18(16)19/h5-12,19-20H,13-14H2,1-4H3,(H,27,28)/t20-/m0/s1

Upstream product

• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 197632-85-2 N-Me-Asp(OtBu)-OH 
• 67-56-1 methanol 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 3057-74-7 L-Asp(t-Bu) 

Downstream Products

• 1599485-70-7 C₃₂H₄₃N₃O₇ 
• 1599485-76-3 C₂₀H₃₀N₂O₅S₂ 

Relevant articles and documents

Synthesis method of N-methyl-(2S)-2-N-fluorenylmethoxycarbonylamino-aspartic acid (4-tert-butyl ester)

The invention relates to a synthesis method of N-methyl-(2S)-2-N-fluorenylmethoxycarbonyl amino-aspartic acid (4-tert-butyl ester). The method mainly solves the technical problem of product racemization and the problem of large-scale production in the existing synthesis method. The preparation method comprises the following four steps: step 1, dissolving a raw material A in tetrahydrofuran, addingcesium carbonate and methyl iodide to obtain a compound 1, and directly applying the product to the next step of reaction without purification; 2, at room temperature, introducing hydrogen into the compound 1 to react in methanol, and carrying out palladium-carbon catalysis to obtain a compound 2; 3, dissolving the compound 2 in methyl alcohol, adding L-(-)-diacetyl tartaric acid, and carrying out salifying treatment until ee is larger than 99%, so that a compound 3 is obtained, 4, performing a reaction on the compound 3 with acetone and sodium hydroxide, adding Fmoc-OSu is added for a reaction, and performing hydrochloric acid acidification to obtain the target compound 4.