CALISTO-LACTONE

Base Information

• Chemical Name: CALISTO-LACTONE
• CAS No.: 186833-31-8
• Molecular Formula: C₁₀H₁₅NO₄
• Molecular Weight: 213.233
• Mol file: 186833-31-8.mol

Synonyms:6-Oxa-2-azabicyclo[3.2.0]heptane-3,7-dione,1-(1-hydroxy-2-methylpropyl)-4-methyl-, [1R-[1a(S*),4b,5a]]-; (-)-Omuralide; Omuralide;clasto-Lactacystin b-lactone; b-Clastolactacystin;b-Lactacystin

Chemical Property of CALISTO-LACTONE

Chemical Property:

• Vapor Pressure: 1.27E-09mmHg at 25°C
• Refractive Index: 1.523
• Boiling Point: 440.8°Cat760mmHg
• Flash Point: 220.4°C
• PSA: 75.63000
• Density: 1.28g/cm³
• LogP: -0.23780

Purity/Quality:

98% ^*data from raw suppliers

CALISTO-LACTONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of CALISTO-LACTONE

There total 187 articles about CALISTO-LACTONE 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

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.