Gilvocarcin V

Base Information

• Chemical Name: Gilvocarcin V
• CAS No.: 77879-90-4
• Molecular Formula: C₂₇H₂₆O₉
• Molecular Weight: 494.498
• Nikkaji Number: J354.404D
• Wikipedia: Gilvocarcin_V
• Wikidata: Q72480216
• Metabolomics Workbench ID: 109827
• ChEMBL ID: CHEMBL5174285
• Mol file: 77879-90-4.mol

Synonyms:2064A;4-fucofuranose-1-hydroxy-10,12-dimethoxy-8-vinyl-6H-benz(d)naphtho(1,2b)pyran-6-one;gilvocarcin V

Chemical Property of Gilvocarcin V

Chemical Property:

• Vapor Pressure: 9.65E-28mmHg at 25°C
• Melting Point: 265.5°C
• Refractive Index: 1.5500 (estimate)
• Boiling Point: 810.3°C at 760 mmHg
• Flash Point: 276.1°C
• PSA: 138.82000
• Density: 1.44g/cm³
• LogP: 3.00770
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 5
• Exact Mass: 494.15768240
• Heavy Atom Count: 36
• Complexity: 821

Purity/Quality:

99% ^*data from raw suppliers

Gilvocarcin V ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1C(C(C(O1)C2=C3C(=C(C=C2)O)C(=CC4=C3OC(=O)C5=C4C(=CC(=C5)C=C)OC)OC)O)O)O
• Isomeric SMILES: C[C@H]([C@H]1[C@@H]([C@H]([C@H](O1)C2=C3C(=C(C=C2)O)C(=CC4=C3OC(=O)C5=C4C(=CC(=C5)C=C)OC)OC)O)O)O
• Uses: Gilvocarcin V is the major analogue of a complex of C-glycoside antitumour actives isolated from a Streptomyces sp.. Gilvocarcin V contains a vinyl group in the 8-position, and is the most potent analogue of the complex. It is thought to act as an inhibitor of the catalytic activity of human topoisomerase II. The metabolite displays potent antibacterial, antifungal, antiviral and antitumour activity. Recent research suggests that the gilvocarcins act as photoactivated crosslinkers of DNA to histones. Gilvocarcin V is the major analogue of a complex of C-glycoside antitumor actives isolated from a Streptomyces sp.. Gilvocarcin V contains a vinyl group in the 8-position, and is the most potent analogue of the complex. It is thought to act as an inhibitor of the catalytic activity of human topoisomerase II. The metabolite displays potent antibacterial, antifungal, antiviral and antitumor activity. Recent research suggests that the gilvocarcins act as photoactivated cross-linkers of DNA to histones. Gilvocarcin V is a metabolite that displays potent antibacterial, antifungal and antiviral activity.

Technology Process of Gilvocarcin V

There total 2 articles about Gilvocarcin V 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:

gilvocarcin V (77879-90-4,78037-26-0) → 4-β-fucofuranosyl-1-hydroxy-10,12-dimethoxy-8-vinyl-6H-benzo-naphtho<1,2-b> pyran-6-one (86475-86-7) + 4-α-fucofuranosyl-1-hydroxy-10,12-dimethoxy-8-vinyl-6H-benzo-naphtho<1,2-b> pyran-6-one (77879-90-4,78037-26-0)

Guidance literature:

With toluene-4-sulfonic acid; In acetonitrile; for 10h; Product distribution; Heating; other reagent and solvent;

DOI:10.1016/S0040-4020(01)91834-4

Reference yield:

gilvocarcin V (77879-90-4,78037-26-0) → 4-α-fucofuranosyl-1-hydroxy-10,12-dimethoxy-8-vinyl-6H-benzo-naphtho<1,2-b> pyran-6-one (77879-90-4,78037-26-0) + 1-Hydroxy-10,12-dimethoxy-4-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yl)-8-vinyl-dibenzo[c,h]chromen-6-one

Guidance literature:

Heating;

Reference yield:

gilvocarcin V (77879-90-4,78037-26-0) → 4-β-fucofuranosyl-1-hydroxy-10,12-dimethoxy-8-vinyl-6H-benzo-naphtho<1,2-b> pyran-6-one (86475-86-7) + 4-α-fucofuranosyl-1-hydroxy-10,12-dimethoxy-8-vinyl-6H-benzo-naphtho<1,2-b> pyran-6-one (77879-90-4,78037-26-0)

Guidance literature:

With toluene-4-sulfonic acid; In acetonitrile; for 10h; Product distribution; Heating; other reagent and solvent;

DOI:10.1016/S0040-4020(01)91834-4

upstream raw materials:

gilvocarcin V

Downstream raw materials:

4-β-fucofuranosyl-1-hydroxy-10,12-dimethoxy-8-vinyl-6H-benzo-naphtho<1,2-b> pyran-6-one

4-α-fucofuranosyl-1-hydroxy-10,12-dimethoxy-8-vinyl-6H-benzo-naphtho<1,2-b> pyran-6-one

Refernces

• 1、 Jain,Simolike,Jackman. "Structure and stereochemistry or toromycin: Studies of its acid-catalyzed rearrangement". . p. 599 - 605. Retrieved 2007/10/02.