Fmoc-D-tert-leucine

Base Information

• Chemical Name: Fmoc-D-tert-leucine
• CAS No.: 198543-64-5
• Molecular Formula: C21H23 N O4
• Molecular Weight: 353.418
• Hs Code.: 2924 29 70
• DSSTox Substance ID: DTXSID30359659
• Wikidata: Q72478947
• Mol file: 198543-64-5.mol

Synonyms:Fmoc-D-tert-leucine;198543-64-5;Fmoc-D-Tle-OH;fmoc-d-alpha-t-butylglycine;Fmoc-D-alpha-tert-butylglycine;(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3,3-dimethylbutanoic acid;D-Valine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-3-methyl-;(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3,3-dimethylbutanoic acid;Fmoc-D-alpha-tert-butyl-Gly-OH;Fmoc-D-tBu-Gly-OH;SCHEMBL13946516;DTXSID30359659;Fmoc-D- alpha -tert-butyl-Gly-OH;MFCD00065650;AKOS025289356;Fmoc-D-alpha-t-butylglycine, AldrichCPR;CS-0101040;D81917;EN300-624021;(R)-N-Fmoc-2-amino-3,3-dimethyl-butyric acid;A879972;J-012823;Z1606763424;(R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3,3-dimethylbutanoic acid;(2R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3,3-dimethylbutanoic acid

Chemical Property of Fmoc-D-tert-leucine

Chemical Property:

• Melting Point: 126-130oC
• Boiling Point: 554.1±33.0 °C(Predicted)
• PKA: 3.92±0.10(Predicted)
• PSA: 75.63000
• Density: 1.209±0.06 g/cm3(Predicted)
• LogP: 4.41530
• Storage Temp.: -15°C
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 353.16270821
• Heavy Atom Count: 26
• Complexity: 505

Purity/Quality:

99% ^*data from raw suppliers

Fmoc-D-Tle-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Fmoc-D-tert-leucine

There total 1 articles about Fmoc-D-tert-leucine 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:

[(E)-1-tert-Butyl-3-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-allyl]-carbamic acid 9H-fluoren-9-ylmethyl ester → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3,3-dimethylbutanoic acid (132684-60-7) + Fmoc-D-tert-leucine (198543-64-5)

Guidance literature:

[(E)-1-tert-Butyl-3-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-allyl]-carbamic acid 9H-fluoren-9-ylmethyl ester; With ozone; In dichloromethane; at -78 ℃; for 0.133333h;

With dimethylsulfide; In dichloromethane; at -78 - 20 ℃; for 3h;

With jones' reagent; In acetone; at 20 ℃; for 4h; Title compound not separated from byproducts;

DOI:10.1021/ol052034n

Reference yield:

Fmoc-Val-OH (68858-20-8) + Fmoc-L-Thz-(L-Val)-OH + C31H29N2O5Pol + N-(9-fluorenylmethoxycarbonyl)-D-valine (84624-17-9) + trifluoroacetic acid (76-05-1) + Fmoc-D-tert-leucine (198543-64-5) + 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester (143824-78-6,163619-04-3) → (x)C2HF3O2*C46H65N9O7S

Guidance literature:

C₃₁H₂₉N₂O₅Pol; With morpholine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 20 ℃; for 0.25h; TentaGel S resin fused with 3-methoxy-4-(hydroxymethyl)phenoxyacetic acid Inert atmosphere;

Fmoc-Val-OH; With 4-methyl-morpholine; 1-hydroxy-7-aza-benzotriazole; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; TentaGel S resin fused with 3-methoxy-4-(hydroxymethyl)phenoxyacetic acid Inert atmosphere;

Fmoc-L-Thz-(L-Val)-OH; N-(9-fluorenylmethoxycarbonyl)-D-valine; trifluoroacetic acid; Fmoc-D-tert-leucine; 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester; Further stages;

DOI:10.1021/acs.jmedchem.0c02170

Reference yield:

Fmoc-D-tert-leucine (198543-64-5) → (R)-N-benzyl 2-amino-3,3-dimethylbutanamide (268556-62-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: DIPEA; HBTU / acetonitrile / 0.02 h

1.2: acetonitrile / 2 h

2.1: 895 mg / Et₂NH / methanol / 0.42 h

With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; diethylamine; N-ethyl-N,N-diisopropylamine; In methanol; acetonitrile; 1.1: Substitution / 1.2: Substitution / 2.1: deFmoc;

DOI:10.1021/ol005636+

Downstream raw materials:

(R)-N-benzyl 2-amino-3,3-dimethylbutanamide

((R)-1-Benzylcarbamoyl-2,2-dimethyl-propyl)-carbamic acid 4-nitro-phenyl ester

Refernces