(-)-glyceollin I

Base Information

• Chemical Name: (-)-glyceollin I
• CAS No.: 57103-57-8
• Molecular Formula: C20H18 O5
• Molecular Weight: 338.36
• ChEMBL ID: CHEMBL1774989
• Wikidata: Q105348825
• Mol file: 57103-57-8.mol

Synonyms:(-) - glyceollin I;Rac-Glyceollin I;CHEMBL1774989;SCHEMBL12315008;2,2-Dimethyl-2H,6H-benzofuro[3,2-c]pyrano[2,3-h][1]benzopyran-6a,9(11aH)-diol, 9CI

Chemical Property of (-)-glyceollin I

Chemical Property:

• Vapor Pressure: 5.97E-12mmHg at 25°C
• Boiling Point: 527.4°Cat760mmHg
• Flash Point: 272.7°C
• PSA: 68.15000
• Density: 1.397g/cm³
• LogP: 3.29010
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 338.11542367
• Heavy Atom Count: 25
• Complexity: 574

Purity/Quality:

99% ^*data from raw suppliers

Glyceollin I ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C=CC2=C(O1)C=CC3=C2OCC4(C3OC5=C4C=CC(=C5)O)O)C

Technology Process of (-)-glyceollin I

There total 40 articles about (-)-glyceollin I 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: 90.0%

(-)-9-(t-butyldimethylsilyloxy) glyceollin I (1072145-68-6) → (+)-Glyceollin I (57103-57-8)

Guidance literature:

With triethylamine tris(hydrogen fluoride); In pyridine; dichloromethane; at 20 ℃; for 6h; Inert atmosphere;

DOI:10.1021/op200112g

Reference yield: 69.0%

(+)-9-(t-butyldimethylsilyloxy)glyceollin I → (+/-)-glyceollin I (57103-57-8)

Guidance literature:

With triethylamine tris(hydrogen fluoride); In acetonitrile; at -20 - 4 ℃;

Reference yield: 69.0%

(+/-)-9-(t-butyldimethylsilyloxy)glyceollin I (1301254-03-4) → (+/-)-glyceollin I (57103-57-8)

Guidance literature:

With triethylamine tris(hydrogen fluoride); In acetonitrile; at -20 - 4 ℃; Inert atmosphere;

DOI:10.1021/jm101619e

upstream raw materials:

2,4-Dihydroxybenzaldehyde

4-benzoxy-salicylaldehyde

2-hydroxy-4-(methoxymethoxy)acetophenone

2',4'-dihydroxy-4-acetophenone

Refernces

• 1、 Khupse, Rahul S.,Sarver, Jeffrey G.,Trendel, Jill A.,Bearss, Nicole R.,Reese, Michael D.,Wiese, Thomas E.,Boue, Stephen M.,Burow, Matthew E.,Cleveland, Thomas E.,Bhatnagar, Deepak,Erhardt, Paul W.. "Biomimetic syntheses and antiproliferative activities of racemic, natural (-), and unnnatural (+) glyceollin i". . p. 3506 - 3523. Retrieved 2011/07/30.
• 2、 Khupse, Rahul S.,Erhardt, Paul W.. "Total syntheses of racemic, natural (-) and unnatural (+) glyceollin I". supporting information; experimental part. p. 5007 - 5010. Retrieved 2009/05/31.