Fmoc-asp-otbu

Base Information

• Chemical Name: Fmoc-asp-otbu
• CAS No.: 129460-09-9
• Molecular Formula: C₂₃H₂₅NO₆
• Molecular Weight: 411.455
• Hs Code.: 29224999
• European Community (EC) Number: 675-834-7
• DSSTox Substance ID: DTXSID20426920
• Nikkaji Number: J1.085.238B
• Wikidata: Q72478031
• Mol file: 129460-09-9.mol

Synonyms:fmoc-asp-otbu;129460-09-9;(S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid;Fmoc-Asp(OH)-OtBu;fmoc-asp-obut;L-Fmoc-aspartic acid alpha-t-butyl ester;(3S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoic acid;1-tert-Butyl N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-aspartate;N-Fmoc-L-aspartic Acid 1-tert-Butyl Ester;MFCD00065631;Fmoc Asp-OtBu;Fmoc-L-Asp-OtBu;fmoc-asp-otbu, AldrichCPR;SCHEMBL2313063;DTXSID20426920;1-tert-Butyl N-Fmoc-L-aspartate;VZXQYACYLGRQJU-IBGZPJMESA-N;AMY22604;AKOS015920007;AKOS015922864;AKOS032960715;AC-6592;CS-W011675;HY-W010959;L-Fmoc-aspartic acid a-tert-butyl ester;AS-15816;F0503;EN300-1556502;n-alpha-fmoc-l-aspartic acid alpha-t-butyl ester;J-300078;(S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-succinic acid tert-butyl ester;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-aspartic Acid 1-tert-Butyl Ester;(3S)-4-(tert-butoxy)-3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-4-oxobutanoic acid;(R)-2-(((9H-fluoren-9-yl)methoxy)carbonyl)-2-tert-butylsuccinic acid;(S)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-tert-butoxy-4-oxobutanoic acid

Chemical Property of Fmoc-asp-otbu

Chemical Property:

• Vapor Pressure: 4.21E-16mmHg at 25°C
• Melting Point: 90-98°C
• Refractive Index: 1.576
• Boiling Point: 617.4 °C at 760 mmHg
• PKA: 4.08±0.19(Predicted)
• Flash Point: 327.2 °C
• PSA: 101.93000
• Density: 1.251 g/cm³
• LogP: 4.10100
• Storage Temp.: Store at RT.
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 411.16818752
• Heavy Atom Count: 30
• Complexity: 620

Purity/Quality:

98.0% ^*data from raw suppliers

Fmoc-Asp-OtBu ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C(CC(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: CC(C)(C)OC(=O)[C@H](CC(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Uses: Fmoc-Asp-OtBu, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.

Technology Process of Fmoc-asp-otbu

There total 7 articles about Fmoc-asp-otbu 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: 99.0%

2-(9H-fluoren-9-ylmethoxycarbonylamino)-succinic acid 4-allyl ester 1-tert-butyl ester → Fmoc-Asp-O-t-Bu (129460-09-9,134098-70-7)

Guidance literature:

[(cyclopentadienyl)bis(acetonitrile)(triphenylphosphine)ruthenium(II)] hexafluorophosphate; In methanol; at 25 ℃; for 17h;

DOI:10.1021/jo020281o

Reference yield: 99.0%

(S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)succinic acid 4-benzyl ester 1-tert-butyl ester (168261-64-1) → Fmoc-Asp-O-t-Bu (129460-09-9,134098-70-7)

Guidance literature:

With hydrogen; palladium; In ethanol; for 8h;

DOI:10.1016/S0957-4166(99)00013-0

Reference yield:

L-Aspartic acid (56-84-8,25608-40-6,27881-03-4,32505-46-7,52526-39-3) + 9-fluorenylmethyl N-succinimidyl carbonate (102774-86-7) + isobutene (115-11-7,15220-85-6) → Fmoc-(tBu)Asp-OH (71989-14-5) + N-(9-fluorenylmethoxycarbonyl)aspartic acid di-tert-butyl ester (129460-17-9) + Fmoc-Asp-O-t-Bu (129460-09-9,134098-70-7)

Guidance literature:

With sodium carbonate; toluene-4-sulfonic acid; Yield given. Multistep reaction. Yields of byproduct given; 1) dioxane, gas pressure: 350 mbar, 3 d, r.t., 2) dioxane, 0 deg C to r.t., 14 h;

DOI:10.1055/s-1990-26943

upstream raw materials:

L-Aspartic acid

9-fluorenylmethyl N-succinimidyl carbonate

isobutene

(S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)succinic acid 4-benzyl ester 1-tert-butyl ester

Downstream raw materials:

N^α-fluorenylmethoxycarbonyl-L-aspartic acid α-tert-butyl-β-pentafluorophenyl ester

methyl-6-O-carboxy-(N-(9-fluorenylmethoxycarbonyl)-L-aspartic-acid α-tert-butyl ester)-2,3,4-tri-O-4-methoxybenzyl-α-D-manno-pyranoside

Fmoc-Asp(ODMNB)-OH

tert-butyl N₂-[(benzyloxy)carbonyl]-N₅-(N,N'-bis[(benzyloxy)carbonyl]carbamimidoyl)-D-ornithyl-N₄-(4-[(2-tert-butyl-6-methoxyquinolin-8-yl)amino]pentyl)-L-asparaginate

Refernces

• 1、 -. "Preparation method of aspartic acid-1-tert-butyl ester derivative". . . Retrieved 2017/05/02.
• 2、 Van Ameijde, Jeroen,Albada, H. Bauke,Liskamp, Rob M.J.. "A convenient preparation of several N-linked glycoamino acid building blocks for efficient solid-phase synthesis of glycopeptides". . p. 1042 - 1049. Retrieved 2007/10/03.