Fmoc-L-Allylglycine

Base Information

• Chemical Name: Fmoc-L-Allylglycine
• CAS No.: 146549-21-5
• Molecular Formula: C20H19NO4
• Molecular Weight: 337.375
• Hs Code.: 29242990
• DSSTox Substance ID: DTXSID20370318
• Nikkaji Number: J2.118.844A
• Wikidata: Q72477739
• Mol file: 146549-21-5.mol

Synonyms:146549-21-5;Fmoc-L-Allylglycine;Fmoc-Gly(allyl)-OH;Fmoc-L-Allyglycine;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)pent-4-enoic acid;Fmoc-allyl-L-glycine;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)pent-4-enoic acid;Fmoc-alpha-allyl-L-Gly;4-Pentenoic acid, 2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-, (2S)-;Fmoc-allyl-Gly-OH;(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)pent-4-enoic acid;MFCD01311749;Fmoc-Algly-OH;Fmoc-(S)-2-Allylglycine;SCHEMBL118892;DTXSID20370318;fmoc-(s)-2-amino-4-pentenoic acid;AKOS015948715;AC-9626;CS-W008560;FS-5034;HY-W008560;Fmoc-allyl-Gly-OH, >=98.0% (HPLC);EN300-749560;F12324;Fmoc-|A inverted exclamation mark-allyl-L-Gly;A808520;J-300320;N-(9H-Fluorene-9-ylmethoxycarbonyl)-2-allyl-L-glycine;S-146549-21-5;(2S)-2-{[(9H-Fluoren-9-ylmethoxy)carbonyl]amino}-4-pentenoic acid;(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-pentenoic acid;(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)pent-4-enoic acid

Chemical Property of Fmoc-L-Allylglycine

Chemical Property:

• Appearance/Colour: white to almost white powder
• Vapor Pressure: 1.64E-13mmHg at 25°C
• Melting Point: 137.1 °C
• Refractive Index: 1.602
• Boiling Point: 563 °C at 760 mmHg
• PKA: 3.72±0.10(Predicted)
• Flash Point: 294.3 °C
• Density: 1.245 g/cm³
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Slightly soluble in water.
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 337.13140809
• Heavy Atom Count: 25
• Complexity: 484

Purity/Quality:

FMoc-L-Allylglycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C=CCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: C=CC[C@@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Uses: 2-Allyl-N-Fmoc-L-glycine is potentially useful for solid phase peptide synthesis techniques. 2-Allyl-N-Fmoc-L-glycine compound could be useful as an unusual amino acid analog to aid in the deconvolution of protein structure and function. Reagent in the synthesis of a Dicarba-Analog of Octreotide.

Technology Process of Fmoc-L-Allylglycine

There total 15 articles about Fmoc-L-Allylglycine 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: 97.0%

(2S)-2-allyl-N-<(fluoren-9-yl)methoxycarbonyl>glycine prop-2-enyl ester (146549-17-9) → 2-(9H-fluoren-9-ylmethoxycarbonylamino)-pent-4-enoic acid (146549-21-5)

Guidance literature:

With water; chlortris(triphenylphosphine)rhodium; In ethanol; for 2h;

DOI:10.1002/hlca.19920750812

Reference yield: 96.0%

L-allylglycine (16338-48-0) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → 2-(9H-fluoren-9-ylmethoxycarbonylamino)-pent-4-enoic acid (146549-21-5)

Guidance literature:

With sodium hydrogencarbonate; In water; acetone; at 20 ℃; for 20h;

Reference yield: 96.0%

L-allylglycine + 9-fluorenylmethyl N-succinimidyl carbonate (102774-86-7) → 2-(9H-fluoren-9-ylmethoxycarbonylamino)-pent-4-enoic acid (146549-21-5)

Guidance literature:

L-allylglycine; 9-fluorenylmethyl N-succinimidyl carbonate; With sodium hydrogencarbonate; In water; acetone; at 20 ℃; for 20h;

With hydrogenchloride; In water; acetone; pH=2;

upstream raw materials:

(2S)-2-allyl-N-<(fluoren-9-yl)methoxycarbonyl>glycine prop-2-enyl ester

L-allylglycine

(fluorenylmethoxy)carbonyl chloride

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

Downstream raw materials:

(S)-2-[(S)-2-((S)-2-{(S)-2-[(S)-2-((S)-2-tert-Butoxycarbonylamino-pent-4-enoylamino)-propionylamino]-pent-4-enoylamino}-pent-4-enoylamino)-3-(trityl-carbamoyl)-propionylamino]-pent-4-enoic acid methyl ester

benzyl (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)pent-4-enoate

(2S,2'S)-3-allyloxy-2-{(2,4-dimethoxybenzyl)-[2'-(9H-fluoren-9-ylmethoxycarbonylamino)-pent-4'-enoyl]-amino}-propionic acid methyl ester

(2R,2'S)-3-allylsulfanyl-2-{(2,4-dimethoxybenzyl)-[2'-(9H-fluoren-9-ylmethoxycarbonylamino)-pent-4'-enoyl]-amino}-propionic acid methyl ester

Refernces

• 1、 Simon, Justine F.,Lamborelle, Nicolas,Zervosen, Astrid,Lemaire, Christian,Joris, Bernard,Luxen, André. "Development of solid-supported methodology for the preparation of peptidoglycan fragments containing (2S,6R)-diaminopimelic acid". . p. 1572 - 1575. Retrieved 2016.
• 2、 Otani, Takuya,Hattori, Yasunao,Akaji, Kenichi,Kobayashi, Kazuya. "Macrocyclic BACE1 inhibitors with hydrophobic cross-linked structures: Optimization of ring size and ring structure". . . Retrieved 2021/11/22.