Fmoc-N-Me-Asp(OtBu)-OH

Base Information

• Chemical Name: Fmoc-N-Me-Asp(OtBu)-OH
• CAS No.: 152548-66-8
• Molecular Formula: C24H27NO6
• Molecular Weight: 425.481
• Hs Code.: 2924 29 70
• European Community (EC) Number: 802-787-3
• Wikidata: Q76393729
• Mol file: 152548-66-8.mol

Synonyms:Fmoc-N-Me-Asp(OtBu)-OH;152548-66-8;Fmoc-MeAsp(OtBu)-OH;fmoc-n-methyl-l-aspartic acid 4-tert-butyl ester;(2S)-2-[9H-fluoren-9-ylmethoxycarbonyl(methyl)amino]-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoic acid;MFCD00237027;(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid;Fmoc-L-MeAsp(tBu)-OH;N-Fmoc-N-methyl-L-aspartic Acid 4-tert-Butyl Ester;Fmoc-N-Me-L-Asp(OtBu)-OH;SCHEMBL1759730;CYWWLVIEAOUXGW-FQEVSTJZSA-N;N-alpha-Fmoc-N-alpha-methyl-L-aspartic acid beta-t-butyl ester;Fmoc-N-Me-Asp(OtBu)-OH, 97%;AKOS015895306;AM84484;CS-W014456;HY-W013740;N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-alpha-methyl-L-aspartic acid beta-t-butyl ester;AC-31987;DS-13719;F12339;A809323;Fmoc-N-methyl-L-aspartic acid b-tert-butyl ester;Fmoc-Nalpha-methyl-L-aspartic acid beta-t-butylester;Fmoc-Nalpha-methyl-L-aspartic acid beta-t-butyl ester;(S)-2-[(9H-fluoren-9-ylmethoxycarbonyl)-methyl-amino]-succinic acid 4-tert-butyl ester;(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-4-tert-butoxy-4-oxobutanoic acid;4Fmoc-N-methyl-L-aspartic acid 4-tert-butyl esterN-(9-Fluorenylmethyloxycarbonyl)-N-methyl-L-aspartic acid 4-tert-butyl ester

Chemical Property of Fmoc-N-Me-Asp(OtBu)-OH

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 3.52E-15mmHg at 25°C
• Melting Point: 135-140°C
• Refractive Index: 1.574
• Boiling Point: 598.7 °C at 760 mmHg
• PKA: 3.59±0.23(Predicted)
• Flash Point: 315.9 °C
• PSA: 93.14000
• Density: 1.237 g/cm³
• LogP: 4.05230
• Storage Temp.: -15°C
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 425.18383758
• Heavy Atom Count: 31
• Complexity: 650

Purity/Quality:

≥98%, ^*data from raw suppliers

Fmoc-N-Me-Asp(OtBu)-OH Novabiochem? ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)CC(C(=O)O)N(C)C(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: CC(C)(C)OC(=O)C[C@@H](C(=O)O)N(C)C(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• 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.

Technology Process of Fmoc-N-Me-Asp(OtBu)-OH

There total 2 articles about Fmoc-N-Me-Asp(OtBu)-OH which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.5%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + N-Me-Asp(OtBu)-OH (197632-85-2,2044709-83-1) → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid (152548-66-8)

Guidance literature:

With water; sodium hydroxide; In acetone; at 30 ℃; for 12h; pH=9.5; pH-value; Large scale;

Reference yield:

methanol (67-56-1) + (fluorenylmethoxy)carbonyl chloride (28920-43-6) + L-Asp(t-Bu) (3057-74-7) → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid (152548-66-8)

Guidance literature:

Yield given. Multistep reaction;

DOI:10.1016/S0040-4039(97)01774-7

Reference yield: 99.0%

N-BOC-1,2-diaminoethane (57260-73-8) + (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid (152548-66-8) → C32H43N3O7 (1599485-70-7)

Guidance literature:

With 2,4,6-trimethyl-pyridine; dicyclohexyl-carbodiimide; ethyl cyanoglyoxylate-2-oxime; In dichloromethane; for 16h;

upstream raw materials:

methanol

(fluorenylmethoxy)carbonyl chloride

L-Asp(t-Bu)

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

Downstream raw materials:

(NMe)Asp(NMe)Ile(NMe)Ala

C₃₂H₄₃N₃O₇

C₂₀H₃₀N₂O₅S₂

Refernces

• 1、 Yang, Lihu,Chiu, Kuenley. "Solid phase synthesis of Fmoc N-methyl amino acids: Application of the Fukuyama amine synthesis". . p. 7307 - 7310. Retrieved 2007/10/03.