Granatcin-A

Base Information

• Chemical Name: Granatcin-A
• CAS No.: 19879-06-2
• Molecular Formula: C₂₂H₂₀O₁₀
• Molecular Weight: 444.395
• DSSTox Substance ID: DTXSID30941730
• Mol file: 19879-06-2.mol

Synonyms:Granatcin-A;DTXSID30941730;7,8,9,12-Tetrahydroxy-5,15-dimethyl-3,3a,5,8,9,10,11,13b-octahydro-2H-11,8-(epoxymethano)anthra[2,3-d]furo[3,2-b]pyran-2,6,13-trione

Chemical Property of Granatcin-A

Chemical Property:

• Vapor Pressure: 1.6E-23mmHg at 25°C
• Melting Point: 211-213° (dec)
• Refractive Index: 1.5376 (estimate)
• Boiling Point: 748.3°Cat760mmHg
• PKA: 6.56±0.70(Predicted)
• Flash Point: 266.8°C
• PSA: 159.82000
• Density: 1.77g/cm³
• LogP: 0.28820
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 0
• Exact Mass: 444.10564683
• Heavy Atom Count: 32
• Complexity: 958

Purity/Quality:

99%, ^*data from raw suppliers

GRANATICIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2=C(C3C(O1)CC(=O)O3)C(=C4C(=C2O)C(=O)C5=C(C4=O)C6CC(C5(C(O6)C)O)O)O

Technology Process of Granatcin-A

There total 4 articles about Granatcin-A 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:

(3aR*,5R*,8R*,9S*,11S*,13bR*,15S*)-8,9-dihydroxy-6,7,12,13-tetramethoxy-5,15-dimethyl-3,3a,5,8,9,10,11,13b-octahydro-11,8-(epoxymethano)-2H-furo<3,2-b>anthra<2,3-d>pyran-2-one (108168-52-1,108266-36-0,108266-37-1,108266-38-2,124094-68-4) → (+/-)-granaticin (19879-06-2,108267-38-5,108267-39-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / camphorsulfonic acid / tetrahydrofuran / 1 h / Ambient temperature

2: 1.) 18percent aq. ceric ammonium nitrate, 2.) AlCl₃, Et₂S / 1.) MeCN, 25 deg C, 2.) CH₂Cl₂, 0 deg C, 10 min; r.t., 50 min

With aluminium trichloride; ammonium cerium(IV) nitrate; diethyl sulphide; camphor-10-sulfonic acid; In tetrahydrofuran;

DOI:10.1021/ja00245a035

Reference yield:

C26H30O10 (108168-52-1,108266-36-0,108266-37-1,108266-38-2,124094-68-4) → (3aR*,5R*,8S*,9R*,11R*,13bR*,15R*)-7,8,9,12-tetrahydroxy-5,15-dimethyl-6,13-dioxo-3,3a,5,6,8,9,10,11,13,13a-decahydro-11,8-(epoxymethano)-2H-furo<2,3-b>anthra<2,3-d>pyran-2-one (19879-06-2,108267-38-5,108267-39-6)

Guidance literature:

Multi-step reaction with 2 steps

1: camphorsulfonic acid / tetrahydrofuran / 1 h / Ambient temperature

2: 1.) 18percent aq. ceric ammonium nitrate, 2.) AlCl₃, Et₂S / 1.) MeCN, 25 deg C, 2.) CH₂Cl₂, 0 deg C, 10 min; r.t., 50 min

With aluminium trichloride; ammonium cerium(IV) nitrate; diethyl sulphide; camphor-10-sulfonic acid; In tetrahydrofuran;

DOI:10.1021/ja00245a035

Reference yield:

C29H34O10 (108168-53-2,108266-39-3) → (3aR*,5R*,8S*,9R*,11R*,13bR*,15R*)-7,8,9,12-tetrahydroxy-5,15-dimethyl-6,13-dioxo-3,3a,5,6,8,9,10,11,13,13a-decahydro-11,8-(epoxymethano)-2H-furo<2,3-b>anthra<2,3-d>pyran-2-one (19879-06-2,108267-38-5,108267-39-6)

Guidance literature:

With aluminium trichloride; ammonium cerium(IV) nitrate; diethyl sulphide; Yield given. Multistep reaction; 1.) MeCN, 25 deg C, 2.) CH₂Cl₂, 0 deg C, 10 min; r.t., 50 min;

DOI:10.1021/ja00245a035

upstream raw materials:

C₂₉H₃₄O₁₀

(3aR*,5R*,8R*,9S*,11S*,13bR*,15S*)-8,9-dihydroxy-6,7,12,13-tetramethoxy-5,15-dimethyl-3,3a,5,8,9,10,11,13b-octahydro-11,8-(epoxymethano)-2H-furo<3,2-b>anthra<2,3-d>pyran-2-one

C₂₉H₃₄O₁₀

C₂₆H₃₀O₁₀

Refernces