(1S,5beta)-1alpha-[(1S)-1-Hydroxy-2-methylpropyl]-4alpha-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione

Base Information

• Chemical Name: (1S,5beta)-1alpha-[(1S)-1-Hydroxy-2-methylpropyl]-4alpha-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione
• CAS No.: 154226-60-5
• Molecular Formula: C10H15 N O4
• Molecular Weight: 213.233
• European Community (EC) Number: 664-305-6
• ChEMBL ID: CHEMBL490829
• Nikkaji Number: J1.072.764B
• Mol file: 154226-60-5.mol

Synonyms:c-lact compound;clasto-lactacystin beta-lactone;clasto-lactacystin beta-lactone, (1R-(1alpha(S*),4beta,5alpha))-isomer

Chemical Property of (1S,5beta)-1alpha-[(1S)-1-Hydroxy-2-methylpropyl]-4alpha-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione

Chemical Property:

• Melting Point: 186-187°C
• PSA: 75.63000
• LogP: -0.23780
• Storage Temp.: −20°C
• Solubility.: DMF, Ethanol, Hot Ethyl Acetate, Methanol, Pyridine
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 213.10010796
• Heavy Atom Count: 15
• Complexity: 327

Purity/Quality:

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

Clasto-lactacystin(Omuralide) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 20/21/22-37/38-41-36/37/38-25
• Safety Statements: 16-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1C2C(C(=O)O2)(NC1=O)C(C(C)C)O
• Isomeric SMILES: C[C@@H]1[C@H]2[C@@](C(=O)O2)(NC1=O)[C@H](C(C)C)O
• Uses: A cell permeable, irreversible proteasome inhibitor. It is 20-fold more potent than Lactacystin. Lactacytstin spontaneously converts to clasto-lactacystin in biological systems. Clasto-lactacystin is the only cell permeable form of lactacystin. Induces neurite growth and inhibits cell cycle progression similar to lactacytin. Clasto-Lactacystin β-lactone has been used as a proteasomal inhibitor. clasto-Lactacystin beta-lactone is a 20S proteasome and cathepsin A inhibitor.

Technology Process of (1S,5beta)-1alpha-[(1S)-1-Hydroxy-2-methylpropyl]-4alpha-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione

There total 151 articles about (1S,5beta)-1alpha-[(1S)-1-Hydroxy-2-methylpropyl]-4alpha-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione 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: 96.0%

(3R,4S,5R,1'S)-4-hydroxy-5-(1'-hydroxy-2'-methylpropyl)-3-methylpyrrolidin-2-one-5-carboxylic acid (145451-97-4) → omuralide (154226-60-5,186833-31-8,155975-72-7)

Guidance literature:

With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1021/jo048817o

Reference yield: 62.0%

(1R,4R,5S)-1-((S)-1-Hydroxy-2-methyl-propyl)-2-(4-methoxy-benzyl)-4-methyl-6-oxa-2-aza-bicyclo[3.2.0]heptane-3,7-dione (212772-65-1) → omuralide (154226-60-5,186833-31-8,155975-72-7)

Guidance literature:

With ammonium cerium(IV) nitrate; water; In acetonitrile; at 23 ℃; for 1h;

DOI:10.1002/(SICI)1521-3773(19980703)37:12<1676::AID-ANIE1676>3.0.CO;2-T

Reference yield: 55.0%

C10H17NO5 → omuralide (154226-60-5,186833-31-8,155975-72-7)

Guidance literature:

With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1021/jo7027695

upstream raw materials:

(3R,4S,5R,1'S)-4-hydroxy-5-(1'-hydroxy-2'-methylpropyl)-3-methylpyrrolidin-2-one-5-carboxylic acid

(1R,4R,5S)-1-((S)-1-Hydroxy-2-methyl-propyl)-2-(4-methoxy-benzyl)-4-methyl-6-oxa-2-aza-bicyclo[3.2.0]heptane-3,7-dione

(2R,3R,4R,1'S)-(+)-3-hydroxy-2-(1-hydroxy-2-methyl-propyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

(2R,3S)-(-)-2-azido-4-methyl-1-pentane-1,3-diol

Downstream raw materials:

(1R,4R,5S)-1-((R)-1-Hydroxy-2-methyl-propyl)-4-methyl-6-oxa-2-aza-bicyclo[3.2.0]heptane-3,7-dione

Lactacystin

Refernces

• 1、 Yoshioka, Shun,Nagatomo, Masanori,Inoue, Masayuki. "Application of Two Direct C(sp3)-H Functionalizations for Total Synthesis of (+)-Lactacystin". supporting information. p. 90 - 93. Retrieved 2015/07/28.
• 2、 Hayes, Christopher J.,Sherlock, Alexandra E.,Green, Martin P.,Wilson, Claire,Blake, Alexander J.,Selby, Matthew D.,Prodger, Jeremy C.. "Enantioselective total syntheses of omuralide, 7-epi-omuralide, and (+)-lactacystin". . p. 2041 - 2051. Retrieved 2008/09/19.