CLASTO-LACTACYSTIN BETA-LACTONE

Base Information

• Chemical Name: CLASTO-LACTACYSTIN BETA-LACTONE
• CAS No.: 155975-72-7
• Molecular Formula: C₁₀H₁₅NO₄
• Molecular Weight: 213.233
• Mol file: 155975-72-7.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 CLASTO-LACTACYSTIN BETA-LACTONE

Chemical Property:

• Appearance/Colour: White to off-white powder.
• Vapor Pressure: 1.27E-09mmHg at 25°C
• Boiling Point: 440.8 °C at 760 mmHg
• Flash Point: 220.4 °C
• PSA: 66.84000
• Density: 1.28 g/cm³
• LogP: -0.18490
• Storage Temp.: −20°C

Purity/Quality:

99% ^*data from raw suppliers

clasto-Lactacystin β-lactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R20/21/22-37/38-41:
• Hazard Codes: R20/21/22-37/38-41:
• Statements: 20/21/22-37/38-41
• Safety Statements: 16-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of CLASTO-LACTACYSTIN BETA-LACTONE

There total 206 articles about CLASTO-LACTACYSTIN BETA-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: 65.0%

(1S,4R,5R)-1-((R)-1-Hydroxy-2-methyl-propyl)-2-(4-methoxy-benzyl)-4-methyl-6-oxa-2-aza-bicyclo[3.2.0]heptane-3,7-dione (217439-35-5) → (1S,4R,5R)-1-((R)-1-Hydroxy-2-methyl-propyl)-4-methyl-6-oxa-2-aza-bicyclo[3.2.0]heptane-3,7-dione (155975-72-7)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile; at 23 ℃; for 2h;

DOI:10.1016/S0040-4039(98)01797-3

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

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

Refernces

• 1、 Donohoe, Timothy J.,Sintim, Herman O.,Sisangia, Leena,Ace, Karl W.,Guyo, Paul M.,Cowley, Andrew,Harling, John D.. "Utility of the ammonia-free birch reduction of electron-deficient pyrroles: Total synthesis of the 20S proteasome inhibitor, clasto-lactacystin β-lactone". . p. 4227 - 4238. Retrieved 2005.
• 2、 Rullière, Pauline,Cannillo, Alexandre,Grisel, Julien,Cividino, Pascale,Carret, Sébastien,Poisson, Jean-Fran?ois. "Total Synthesis of Proteasome Inhibitor (-)-Omuralide through Asymmetric Ketene [2 + 2]-Cycloaddition". supporting information. p. 4558 - 4561. Retrieved 2018/08/09.
• 3、 Gu, Wenxin,Silverman, Richard B.. "Stereospecific total syntheses of proteasome inhibitors omuralide and lactacystin". experimental part. p. 8287 - 8293. Retrieved 2012/04/10.