Anthra(2,3-b)furo(3,2-d)furan-5,10-dione, 3a,12a-dihydro-4,6-dihydroxy -

Base Information

• Chemical Name: Anthra(2,3-b)furo(3,2-d)furan-5,10-dione, 3a,12a-dihydro-4,6-dihydroxy -
• CAS No.: 30517-65-8
• Molecular Formula: C₁₈H₁₀O₆
• Molecular Weight: 322.274
• Hs Code.: 2932999099
• Mol file: 30517-65-8.mol

Synonyms:Anthra[2,3-b]furo[3,2-d]furan-5,10-dione,3a,12a-dihydro-4,6-dihydroxy- (8CI); Anthra[2,3-b]furo[3,2-d]furan-5,10-dione,3a,12a-dihydro-4,6-dihydroxy-, (3aS-cis)-; 6-Deoxyversicolorin A

Chemical Property of Anthra(2,3-b)furo(3,2-d)furan-5,10-dione, 3a,12a-dihydro-4,6-dihydroxy -

Chemical Property:

• Vapor Pressure: 1.09E-11mmHg at 25°C
• Melting Point: 244.5°C
• Refractive Index: 1.4800 (estimate)
• Boiling Point: 526.1°Cat760mmHg
• Flash Point: 199.3°C
• PSA: 93.06000
• Density: 1.655g/cm³
• LogP: 2.21920

Purity/Quality:

99% ^*data from raw suppliers

ANTHRA(2,3-B)FURO(3,2-D)FURAN-5,10-DIONE, 3A,12A-DIHYDRO-4,6-DIHYDROXY- 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: 6-Deoxyversicolorin A (Anthra[2,3-b]furo[3,2-d]furan-5,10-dione, 3a,12a-dihydro-4,6-dihydroxy-) is an intermediate in aflatoxin biosynthesis but does not directly incorporate into aflatoxin B1, indicating that aromatic deoxygenation does not proceed via its reduction from versicolorin A. Instead, the pathway diverges at versicolorin B, which plays a critical role in determining the formation of tetrahydro- or dihydrobisfuran intermediates.

Technology Process of Anthra(2,3-b)furo(3,2-d)furan-5,10-dione, 3a,12a-dihydro-4,6-dihydroxy -

There total 8 articles about Anthra(2,3-b)furo(3,2-d)furan-5,10-dione, 3a,12a-dihydro-4,6-dihydroxy - 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: 89.0%

C24H16O7S → (+/-)-(3aS-cis)-3a,12a-dihydro-4,6-dihydroxyanthra[2,3-b]furo[3,2-d]furan-5,10-dione (30517-65-8)

Guidance literature:

In toluene; for 0.75h; Heating;

DOI:10.1021/ja990591x

Reference yield:

2,3,3a,12a-tetrahydro-2-hydroxy-4-(methoxymethoxy)-6-[[2-(trimethylsilyl)ethoxy]methoxy]anthra[2,3-b]furo[3,2-d]furan-5,10-dione (122623-66-9) → (+/-)-(3aS-cis)-3a,12a-dihydro-4,6-dihydroxyanthra[2,3-b]furo[3,2-d]furan-5,10-dione (30517-65-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Bu₃P / tetrahydrofuran / 0.08 h / -78 °C

1.2: tetrahydrofuran / 2.5 h / -78 - -25 °C

2.1: 96.3 percent / AcOH; aq. HCl / tetrahydrofuran / 5 h / 65 °C

3.1: m-CPBA / CHCl₃ / -15 °C

4.1: 89 percent / toluene / 0.75 h / Heating

With hydrogenchloride; tributylphosphine; acetic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; chloroform; toluene; 1.1: Addition / 1.2: Substitution / 2.1: Hydrolysis / 3.1: Oxidation / 4.1: Elimination;

DOI:10.1021/ja990591x

Reference yield:

C32H34O8SSi (122623-67-0) → (+/-)-(3aS-cis)-3a,12a-dihydro-4,6-dihydroxyanthra[2,3-b]furo[3,2-d]furan-5,10-dione (30517-65-8)

Guidance literature:

Multi-step reaction with 3 steps

1: AcOH / 6 N aq. HCl / tetrahydrofuran / 60 °C

2: m-CPBA / ethyl acetate / -15 °C

3: toluene; dimethylsulfoxide / 1 h / Heating

With acetic acid; 3-chloro-benzenecarboperoxoic acid; hydrogenchloride; In tetrahydrofuran; dimethyl sulfoxide; ethyl acetate; toluene;

DOI:10.1021/ja00203a057

upstream raw materials:

C₂₄H₁₆O₇S

2,3,3a,12a-tetrahydro-2-hydroxy-4-(methoxymethoxy)-6-[[2-(trimethylsilyl)ethoxy]methoxy]anthra[2,3-b]furo[3,2-d]furan-5,10-dione

C₂₄H₁₆O₆S

C₃₂H₃₄O₈SSi

Refernces

The timing of aromatic deoxygenation in aflatoxin biosynthesis

10.1021/ja00203a057

The research investigates the timing of aromatic deoxygenation in aflatoxin biosynthesis and the partitioning between tetrahydro- and dihydrobisfuran formation in this process. The purpose is to understand the specific steps and intermediates involved in the biosynthesis of aflatoxin B1, a toxic compound produced by certain fungi. Key chemicals used in the research include versicolorin A, 6-deoxyversicolorin A, and various labeled compounds such as [9-13C]versicolorin A. The researchers used cell-free systems and in vivo experiments with fungal cultures to study the conversion of these compounds into aflatoxin B1. The conclusions indicate that versicolorin A efficiently incorporates into aflatoxin B1, while 6-deoxyversicolorin A does not, suggesting that the deoxygenation process does not occur through direct reduction of versicolorin A. Additionally, the research shows that the partitioning between tetrahydro- and dihydrobisfuran formation occurs at the point of versicolorin B formation, highlighting the pivotal role of versicolorin B in the biosynthetic pathway.

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