(-)-Phyllostine

Base Information

• Chemical Name: (-)-Phyllostine
• CAS No.: 27270-89-9
• Molecular Formula: C₇H₆O₄
• Molecular Weight: 154.122
• Hs Code.: 2932999099
• Mol file: 27270-89-9.mol

Synonyms:7-Oxabicyclo[4.1.0]hept-3-ene-2,5-dione,3-(hydroxymethyl)-, (-)- (8CI); 7-Oxabicyclo[4.1.0]hept-3-ene-2,5-dione,3-(hydroxymethyl)-, (1R)-; (-)-Phyllostine; Phyllostin; Phyllostine

Chemical Property of (-)-Phyllostine

Chemical Property:

• Vapor Pressure: 5.07E-08mmHg at 25°C
• Melting Point: 56 °C
• Boiling Point: 398.9°Cat760mmHg
• PKA: 13.40±0.10(Predicted)
• Flash Point: 177.4°C
• PSA: 66.90000
• Density: 1.555g/cm³
• LogP: -1.17570

Purity/Quality:

Analysis control,HPLC≥98% ^*data from raw suppliers

Phyllostine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (-)-Phyllostine

There total 25 articles about (-)-Phyllostine 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: 76.0%

C8H8O6 (649572-58-7) → (5S,6R)-5,6-epoxy-2-hydroxymethylcyclohex-2-ene-1,4-dione (27270-89-9)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; In water; acetone; for 2.5h; cooling;

DOI:10.1016/j.tet.2003.10.065

Reference yield: 72.0%

(1R,6S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-7-oxa-bicyclo[4.1.0]hept-3-ene-2,5-dione (792910-38-4) → (5S,6R)-5,6-epoxy-2-hydroxymethylcyclohex-2-ene-1,4-dione (27270-89-9)

Guidance literature:

With pyridine hydrogenfluoride; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/j.tetlet.2004.08.104

Reference yield: 70.0%

C15H14O5 → (5S,6R)-5,6-epoxy-2-hydroxymethylcyclohex-2-ene-1,4-dione (27270-89-9)

Guidance literature:

With water; trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.166667h;

DOI:10.1002/ejoc.202000486

upstream raw materials:

(+)-5-hydroxy-3-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one

ent-RKTS-33

C₈H₈O₆

(1R,6S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-7-oxa-bicyclo[4.1.0]hept-3-ene-2,5-dione

Downstream raw materials:

ent-RKTS-33

Refernces

• 1、 Kamikubo, Takashi,Hiroya, Kou,Ogasawara, Kunio. "Stereo- and enantio-controlled synthesis of two naturally occurring polyoxygenated cyclohexenemethanols, (+)-epiepoxydon and (-)-phyllostine, via catalytic asymmetrization of a meso substrate". . p. 499 - 502. Retrieved 1996.
• 2、 Chae, Hee Il,Hwang, Geum-Sook,Jin, Ming Yu,Ryu, Do Hyun. "Efficient asymmetric synthesis of chiral monomer of epoxyquinols and (-)-phyllostine". scheme or table. p. 1047 - 1050. Retrieved 2010/11/17.
• 3、 Mehta, Goverdhan,Islam, Kabirul. "Enantioselective total synthesis of epoxyquinone natural products (-)-phyllostine, (+)-epoxydon, (+)-epiepoxydon and (-)-panepophenanthrin: Access to versatile chiral building blocks through enzymatic kinetic resolution". . p. 7683 - 7687. Retrieved 2007/10/03.