(E)-2-Butenyl-4-methyl-threonine

Base Information

• Chemical Name: (E)-2-Butenyl-4-methyl-threonine
• CAS No.: 81135-57-1
• Molecular Formula: C₉H₁₇NO₃
• Molecular Weight: 187.239
• UNII: 46DWS7A8NN
• DSSTox Substance ID: DTXSID701197219
• Metabolomics Workbench ID: 70512
• Nikkaji Number: J704.920J
• Wikidata: Q27110082
• Mol file: 81135-57-1.mol

Synonyms:(4R)-4-((E)-2-butenyl)-4-methyl-L-threonine;2(S)-amino-3(R)-hydroxy-4(R)-methyl-6(E)-octenoic acid;2-amino-3-hydroxy-4-methyl-6-octenoic acid;2-Bmt;2-butenyl-4-methyl-L-threonine;2-butenyl-4-methylthreonine

Chemical Property of (E)-2-Butenyl-4-methyl-threonine

Chemical Property:

• Vapor Pressure: 3.21E-07mmHg at 25°C
• Boiling Point: 376.8°Cat760mmHg
• Flash Point: 181.7°C
• PSA: 83.55000
• Density: 1.116g/cm³
• LogP: 1.06180
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 187.12084340
• Heavy Atom Count: 13
• Complexity: 191

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CCC(C)C(C(C(=O)O)N)O
• Isomeric SMILES: C/C=C/C[C@@H](C)[C@H]([C@@H](C(=O)O)N)O

Technology Process of (E)-2-Butenyl-4-methyl-threonine

There total 4 articles about (E)-2-Butenyl-4-methyl-threonine 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: 81.0%

(E)-(2S,3R,4R)-2-Formylamino-3-hydroxy-4-methyl-oct-6-enoic acid tert-butyl ester (174196-48-6) → (2S,3R,4R,6E)-3-hydroxy-4-methyl-2-amino-oct-6-enoic acid (81135-57-1)

Guidance literature:

With hydrogenchloride; for 24h; Ambient temperature;

Reference yield:

(-)-(2R)-2-methyl-4-hexenal (104372-54-5,519002-37-0) → (2S,3R,4R,6E)-3-hydroxy-4-methyl-2-amino-oct-6-enoic acid (81135-57-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 66.4 percent / NaCN / 2-methyl-propan-2-ol / 1.) 0 deg C, 1 h, 2.) room temperature, 20 h

2: 49 percent / 90percent AcOH / H₂O / 12 h / Ambient temperature

3: 81 percent / 3N HCl / 24 h / Ambient temperature

With hydrogenchloride; sodium cyanide; acetic acid; In water; tert-butyl alcohol;

Reference yield:

(1'R,3'E)-4-tert-butoxycarbonyl-5-(1'-methyl-3'-pentenyl)oxazoline → (2S,3R,4R,6E)-3-hydroxy-4-methyl-2-amino-oct-6-enoic acid (81135-57-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 49 percent / 90percent AcOH / H₂O / 12 h / Ambient temperature

2: 81 percent / 3N HCl / 24 h / Ambient temperature

With hydrogenchloride; acetic acid; In water;

upstream raw materials:

(E)-(2S,3R,4R)-2-Formylamino-3-hydroxy-4-methyl-oct-6-enoic acid tert-butyl ester

(-)-(2R)-2-methyl-4-hexenal

Refernces

• 1、 -. "Method for the total synthesis of cyclosporins, novel cyclosporins and novel intermediates and methods for their production". . . Retrieved 2008/06/13.