FMOC-D-allo-Isoleucine

Base Information

• Chemical Name: FMOC-D-allo-Isoleucine
• CAS No.: 118904-37-3
• Molecular Formula: C21H23NO4
• Molecular Weight: 353.418
• European Community (EC) Number: 834-532-7
• DSSTox Substance ID: DTXSID30426315
• Nikkaji Number: J323.857A
• Wikidata: Q72477722
• Mol file: 118904-37-3.mol

Synonyms:Fmoc-d-allo-ile-oh;118904-37-3;FMOC-D-allo-Isoleucine;(2R,3S)-N-Fmoc-2-Amino-3-Methylpentanoic Acid;(2R,3S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methylpentanoic acid;(2R,3S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-methylpentanoic acid;D-Alloisoleucine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-;(2R,3S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-methylpentanoic acid;MFCD00077062;DTXSID30426315;AKOS015950970;AM81865;CS-W022725;DS-2293;HY-W041985;(2R,3S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)-amino)-3-methylpentanoic acid;EN300-7376874;A804124;N-(9-Fluorenylmethyloxycarbonyl)-D-allo-isoleucine;N-(9H-Fluoren-9-ylmethoxycarbonyl)-D-alloisoleucine;(((9H-Fluoren-9-yl)methoxy)carbonyl)-D-alloisoleucine;N-alpha-(9-Fluorenylmethyloxycarbonyl)-D-allo-isoleucine;(2R,3S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-methylpentanoic acid;N-alpha-(9-Fluorenylmethyloxycarbonyl)-D-allo-isoleucine (Fmoc-D-allo-Ile-OH);(2R,3S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methyl-pentanoic acid;Fmoc-D-allo-isoleucine

Chemical Property of FMOC-D-allo-Isoleucine

Chemical Property:

• Vapor Pressure: 2.28E-13mmHg at 25°C
• Refractive Index: 1.582
• Boiling Point: 559.8 °C at 760 mmHg
• PKA: 3.92±0.22(Predicted)
• Flash Point: 292.4 °C
• PSA: 75.63000
• Density: 1.207 g/cm³
• LogP: 4.41530
• Storage Temp.: Store at RT.
• Water Solubility.: Slightly soluble in water.
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 353.16270821
• Heavy Atom Count: 26
• Complexity: 486

Purity/Quality:

99% ^*data from raw suppliers

Fmoc-D-allo-isoleucine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC(C)C(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: CC[C@H](C)[C@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Uses: Fmoc-D-Allo-Ile-OH is used in preparation of Cyclopeptides simulating natural product structures.

Technology Process of FMOC-D-allo-Isoleucine

There total 1 articles about FMOC-D-allo-Isoleucine 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: 90.0%

N-(9-Fluorenylmethoxycarbonyl)-D-alloisoleucine methyl ester (118878-65-2) → N-(9-Fluorenylmethoxycarbonyl)-D-alloisoleucine (118904-37-3,251316-98-0)

Guidance literature:

With hydrogenchloride; water; In 1,4-dioxane; at 100 ℃; for 48h;

DOI:10.1016/0040-4039(88)85084-6

Reference yield: 11.0%

(S)-N1,N1,3-trimethylbutane-1,2-diamine (847696-16-6,486414-51-1,773045-76-4) + Fmoc-D-OHVal (884880-39-1) + (S)-2,2,4,6-tetramethyl-3-oxoheptanoic acid (1428850-10-5) + C5H7N3O2 + C41H34F6NO5P + C29H34N2O7 + C31H38N2O8 + C32H40N2O8 + N-(9-Fluorenylmethoxycarbonyl)-D-alloisoleucine (118904-37-3,251316-98-0) + N-(9-fluorenylmethoxycarbonyl)-D-alanine (35661-38-2,35661-39-3,79990-15-1,136132-75-7) + N-(9-fluorenylmethoxycarbonyl)-D-valine (84624-17-9) → yaku’amide B

Guidance literature:

C₅H₇N₃O₂; With dmap; dicyclohexyl-carbodiimide; In 1-methyl-pyrrolidin-2-one; dichloromethane; at 20 ℃; for 6h;

C₄₁H₃₄F₆NO₅P; In 1,2-dimethoxyethane; water; at 50 ℃; for 48h;

(S)-N¹,N¹,3-trimethylbutane-1,2-diamine; Fmoc-D-OHVal; (S)-2,2,4,6-tetramethyl-3-oxoheptanoic acid; C₂₉H₃₄N₂O₇; C₃₁H₃₈N₂O₈; C₃₂H₄₀N₂O₈; N-(9-Fluorenylmethoxycarbonyl)-D-alloisoleucine; N-(9-fluorenylmethoxycarbonyl)-D-alanine; N-(9-fluorenylmethoxycarbonyl)-D-valine; Further stages;

DOI:10.1002/anie.201916517

Reference yield: 11.0%

H-Ala-2-chlorotrityl resin + Octanoic acid (124-07-2) + N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-Val-OH (68858-20-8) + N-Fmoc L-Phe (35661-40-6) + N-(9-Fluorenylmethoxycarbonyl)-D-alloisoleucine (118904-37-3,251316-98-0) + (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid (125238-99-5,114360-56-4) + N-(9-fluorenylmethoxycarbonyl)-D-valine (84624-17-9) + 1-tert-butoxycarbonyl-N-[(9-fluorenyl)methoxycarbonyl]-D-tryptophan (163619-04-3) + N-α-(9-fluorenylmethyloxycarbonyl)-N-γ-tert-butyloxycarbonyl-D-2,4-diaminobutyric acid (114360-56-4) → octyl-tridecaptin A1 (1542148-60-6)

Guidance literature:

H-Ala-2-chlorotrityl resin; N-(9-Fluorenylmethoxycarbonyl)-D-alloisoleucine; With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 70 ℃; for 0.0833333h; 2-chlorotrityl resin Automated synthesizer; Microwave irradiation;

With piperidine; In N,N-dimethyl-formamide; at 70 ℃; for 0.0583333h; 2-chlorotrityl resin Automated synthesizer; Microwave irradiation;

Octanoic acid; N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Val-OH; N-Fmoc L-Phe; (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid; N-(9-fluorenylmethoxycarbonyl)-D-valine; 1-tert-butoxycarbonyl-N-[(9-fluorenyl)methoxycarbonyl]-D-tryptophan; N-α-(9-fluorenylmethyloxycarbonyl)-N-γ-tert-butyloxycarbonyl-D-2,4-diaminobutyric acid; Fmoc-Glu(pg)-OH; Fmoc-Ser(pg)-OH; Fmoc-D-Ser(pg)-OH; Further stages;

DOI:10.1039/c9md00031c

upstream raw materials:

N-(9-Fluorenylmethoxycarbonyl)-D-alloisoleucine methyl ester

Downstream raw materials:

Fmoc-D-allo-MeIle-OH

C₅₃H₈₅N₉O₁₄

C₃₈H₆₀N₆O₁₀

C₄₄H₇₁N₇O₁₁

Refernces

• 1、 Schmidt, U.,Kroner, M.,Griesser, H.. "TOTAL SYNTHESIS OF THE DIDEMNINS - 1. SYNTHESIS OF THE PEPTOLIDE RING". . p. 3057 - 3060. Retrieved 2007/10/02.