(-)-6a-Hydroxymaackiain

Base Information

• Chemical Name: (-)-6a-Hydroxymaackiain
• CAS No.: 61218-44-8
• Molecular Formula: C16H12O6
• Molecular Weight: 300.26
• Mol file: 61218-44-8.mol

Synonyms:(-)-6a-Hydroxymaackiain;6a-Hydroxymaackiain;6alpha-Hydroxymaackiain

Chemical Property of (-)-6a-Hydroxymaackiain

Chemical Property:

• Vapor Pressure: 1.39E-11mmHg at 25°C
• Boiling Point: 518.7°C at 760 mmHg
• PKA: 9.34±0.40(Predicted)
• Flash Point: 267.5°C
• PSA: 77.38000
• Density: 1.634g/cm³
• LogP: 1.83460

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

6a-Hydroxymaackiain 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (-)-6a-Hydroxymaackiain

There total 8 articles about (-)-6a-Hydroxymaackiain 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: 80.0%

(3R,4S)-7-Benzyloxy-3-(6-benzyloxy-benzo[1,3]dioxol-5-yl)-chroman-3,4-diol (207232-36-8) → (+)-6a-hydroxymaackiain (14602-93-8,61218-44-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 1.5h;

DOI:10.1016/S0040-4039(98)00299-8

Reference yield:

5-Benzyloxy-2-[(Z)-2-(6-benzyloxy-benzo[1,3]dioxol-5-yl)-3-hydroxy-propenyl]-phenol → (+)-6a-hydroxymaackiain (14602-93-8,61218-44-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent / PPh₃, DEAD / benzene / 12 h / Ambient temperature

2: 90 percent / OsO₄, dihydroquinine, p-chlorobenzoate / CH₂Cl₂ / 24 h / -78 °C

3: 80 percent / hydrogen / 10percent Pd/C / methanol / 1.5 h

With osmium(VIII) oxide; hydrogen; triphenylphosphine; para-chlorobenzoic acid; diethylazodicarboxylate; dihydroquinine; palladium on activated charcoal; In methanol; dichloromethane; benzene;

DOI:10.1016/S0040-4039(98)00299-8

Reference yield:

7-Benzyloxy-3-(6-benzyloxy-benzo[1,3]dioxol-5-yl)-2H-chromene (207232-35-7) → (+)-6a-hydroxymaackiain (14602-93-8,61218-44-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / OsO₄, dihydroquinine, p-chlorobenzoate / CH₂Cl₂ / 24 h / -78 °C

2: 80 percent / hydrogen / 10percent Pd/C / methanol / 1.5 h

With osmium(VIII) oxide; hydrogen; para-chlorobenzoic acid; dihydroquinine; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1016/S0040-4039(98)00299-8

upstream raw materials:

(3R,4S)-7-Benzyloxy-3-(6-benzyloxy-benzo[1,3]dioxol-5-yl)-chroman-3,4-diol

7-Hydroxy-3-(4-methoxy-phenyl)-chromen-4-on

S-adenosyl-L-methionine

7-Benzyloxy-3-(6-benzyloxy-benzo[1,3]dioxol-5-yl)-2H-chromene

Refernces

• 1、 Kaimoyo, Evans,VanEtten, Hans D.. "Inactivation of pea genes by RNAi supports the involvement of two similar O-methyltransferases in the biosynthesis of (+)-pisatin and of chiral intermediates with a configuration opposite that found in (+)-pisatin". . p. 76 - 87. Retrieved 2008/09/18.
• 2、 Pinard, Emmanuel,Gaudry, Michel,Henot, Frederic,Thellend, Annie. "Asymmetric total synthesis of (+)-pisatin, a phytoalexin from garden peas (Pisum sativum L.)". . p. 2739 - 2742. Retrieved 2007/10/03.