Fmoc-Asp-OAll

Base Information

• Chemical Name: Fmoc-Asp-OAll
• CAS No.: 144120-53-6
• Molecular Formula: C22H21NO6
• Molecular Weight: 395.412
• Hs Code.: 2924 29 70
• Mol file: 144120-53-6.mol

Synonyms:Fmoc-L-Aspartic Acid 1-Allyl Ester;Fmoc-Asp-OAll;

Chemical Property of Fmoc-Asp-OAll

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 3.52E-17mmHg at 25°C
• Melting Point: -95oC (dec.)
• Refractive Index: 1.591
• Boiling Point: 634.8 °C at 760 mmHg
• PKA: 4.09±0.19(Predicted)
• Flash Point: 337.7 °C
• PSA: 101.93000
• Density: 1.286 g/cm³
• LogP: 3.48850
• Storage Temp.: 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

Fmoc-asp-oall ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: Fmoc-asp-oall is an intermediate used in the synthesis of some biologically active molecules.

Technology Process of Fmoc-Asp-OAll

There total 4 articles about Fmoc-Asp-OAll 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: 96.0%

4-(1,1-dimethylethyl) ester of Nα-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-aspartic acid allyl ester (144120-52-5) → (S)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)-4-oxobutanoic acid (144120-53-6)

Guidance literature:

With trifluoroacetic acid;

DOI:10.1016/S0040-4039(00)61311-4

Reference yield: 88.0%

N-α-9-fluorenylmethoxycarbonyl-aspartic acid (136083-57-3,136083-73-3,119062-05-4) + allyl alcohol (107-18-6) → (S)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)-4-oxobutanoic acid (144120-53-6)

Guidance literature:

With CLEA-Alcalase; In tert-butyl methyl ether; at 50 ℃; for 16h; Molecular sieve;

DOI:10.1055/s-0028-1083362

Reference yield:

Fmoc-(tBu)Asp-OH (71989-14-5) → (S)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)-4-oxobutanoic acid (144120-53-6)

Guidance literature:

Multi-step reaction with 2 steps

1: N,N'-dicyclohexylcarbodiimide / tetrahydrofuran

2: CF₃CO₂H / CH₂Cl₂ / 0.5 h

With dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0040-4039(93)85003-F

upstream raw materials:

4-(1,1-dimethylethyl) ester of Nα-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-aspartic acid allyl ester

Fmoc-(tBu)Asp-OH

N-α-9-fluorenylmethoxycarbonyl-aspartic acid

allyl alcohol

Downstream raw materials:

N-[1-(1-tert-butoxycarbonyl-2-phenyl-ethylcarbamoyl)-2-(1H-indol-3-yl)-ethyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-succinamic acid allyl ester

2-(9H-fluoren-9-ylmethoxycarbonylamino)-succinic acid 1-allyl ester 4-(2-diphenylphosphanyl-phenyl) ester

N^α-fluorenylmethoxycarbonyl-N^ω-(2-acetamido-3-O-[6-O-benzyl-β-D-galactopyranosyl]-4-O-[2,3,4-tri-O-benzyl-β-D-arabinopyranosyl]-6-O-benzyl-2-deoxy-β-D-glucopyranosyl)-L-asparagine allyl ester

Refernces

• 1、 Thieme, Karena,Schnell, Ingo. "Determination of long-range distances and dynamic order parameters by dipolar recoupling in high-resolution magic-angle spinning NMR spectroscopy". . p. 12100 - 12101. Retrieved 2003.
• 2、 Trzeciak,Bannwarth. "Synthesis of 'head-to-tail' cyclized peptides on solid support by Fmoc chemistry". . p. 4557 - 4560. Retrieved 1992.
• 3、 -. "CANCER IMAGING AND TREATMENT". Paragraph 0150; 0151; 0152. . Retrieved 2014/02/16.
• 4、 Demmer, Oliver,Dijkgraaf, Ingrid,Schumacher, Udo,Marinelli, Luciana,Cosconati, Sandro,Gourni, Eleni,Wester, Hans-Jürgen,Kessler, Horst. "Design, synthesis, and functionalization of dimeric peptides targeting chemokine receptor CXCR4". experimental part. p. 7648 - 7662. Retrieved 2012/01/13.