Fmoc-O-tert-butyl-L-beta-homothreonine

Base Information

• Chemical Name: Fmoc-O-tert-butyl-L-beta-homothreonine
• CAS No.: 353245-99-5
• Molecular Formula: C₂₄H₂₉NO₅
• Molecular Weight: 411.498
• DSSTox Substance ID: DTXSID80375824
• Wikidata: Q72510566
• Mol file: 353245-99-5.mol

Synonyms:353245-99-5;Fmoc-L-beta-homothreonine(OtBu);Fmoc-O-tert-butyl-L-beta-homothreonine;Fmoc-|A-HomoThr(tBu)-OH;(3R,4R)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-[(2-methylpropan-2-yl)oxy]pentanoic acid;(3R,4R)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)pentanoic acid;Fmoc-beta-HoThr(tBu)-OH;MFCD01863057;Fmoc--HomoThr(tBu)-OH;Fmoc-ss-HomoThr(tBu)-OH;SCHEMBL119194;DTXSID80375824;Fmoc-O-t-butyl-L-beta-homothreonine;AKOS022185560;AC-22095;AS-57780;CS-0179086;M06215;A874637;Fmoc-beta-Homothr(tBu)-OH, >=96.0% (HPLC);(3R,4R)-4-(tert-butoxy)-3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)pentanoic acid

Chemical Property of Fmoc-O-tert-butyl-L-beta-homothreonine

Chemical Property:

• Boiling Point: 602.3±55.0 °C(Predicted)
• PKA: 4.21±0.10(Predicted)
• PSA: 84.86000
• Density: 1.180±0.06 g/cm3(Predicted)
• LogP: 4.96290
• Storage Temp.: 2-8°C
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 411.20457303
• Heavy Atom Count: 30
• Complexity: 579

Purity/Quality:

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

Fmoc-l-β-homothreonine(otbu) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(CC(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)OC(C)(C)C
• Isomeric SMILES: C[C@H]([C@@H](CC(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)OC(C)(C)C
• Uses: Fmoc-l-beta-homothreonine(otbu)

Technology Process of Fmoc-O-tert-butyl-L-beta-homothreonine

There total 3 articles about Fmoc-O-tert-butyl-L-beta-homothreonine 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: 75.0%

(3S,4R)-4-(tert-butoxy)-1-diazo-3-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}pentan-2-one (308806-73-7) → (R)-3-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-4-(R)-(tert-butoxy)pentanoic acid (353245-99-5)

Guidance literature:

With 4-methyl-morpholine; silver trifluoroacetate; In tetrahydrofuran; water; at 0 - 20 ℃; for 8h;

DOI:10.1021/jm010816q

Reference yield:

Fmoc-Thr(tBu)-OH (71989-35-0,138797-71-4) → (R)-3-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-4-(R)-(tert-butoxy)pentanoic acid (353245-99-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Et₃N; i-BuOCOCl / tetrahydrofuran / 0.25 h / -25 °C

1.2: 80 percent / tetrahydrofuran; diethyl ether / 0 - 20 °C

2.1: 75 percent / CF₃COOAg; NMM / tetrahydrofuran; H₂O / 8 h / 0 - 20 °C

With 4-methyl-morpholine; silver trifluoroacetate; triethylamine; isobutyl chloroformate; In tetrahydrofuran; water; 2.1: Wolff rearrangement;

DOI:10.1021/jm010816q

Reference yield:

C28H35NO7 → (R)-3-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-4-(R)-(tert-butoxy)pentanoic acid (353245-99-5)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran; diethyl ether / 3 h / -20 - 20 °C

2: 59 percent / H₂O; silver trifluoroacetate; NMM / tetrahydrofuran / 4 h / -20 - 20 °C

With 4-methyl-morpholine; water; silver trifluoroacetate; In tetrahydrofuran; diethyl ether; 2: Wolff rearrangement;

DOI:10.1021/jm000909s

upstream raw materials:

(3S,4R)-4-(tert-butoxy)-1-diazo-3-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}pentan-2-one

Fmoc-Thr(tBu)-OH

Refernces

• 1、 Gademann,Kimmerlin,Hoyer,Seebach. "Peptide folding induces high and selective affinity of a linear and small β-peptide to the human somatostatin receptor 4". . p. 2460 - 2468. Retrieved 2007/10/03.