Dihydroxythiobinupharidine

Base Information

• Chemical Name: Dihydroxythiobinupharidine
• CAS No.: 30343-70-5
• Molecular Formula: C₃₀H₄₂N₂O₄S
• Molecular Weight: 526.74
• Mol file: 30343-70-5.mol

Synonyms:Neothiobinupharidine,6,15-dihydroxy-, (6a,7S,13S,15b)-;Thionuphlutine A, 6,6'-dihydroxy- (8CI); 6,6'-Dihydroxythiobinupharidine;6,6'-Dihydroxythionuphlutine A;Dispiro[2H-quinolizine-3(4H),2'(3'H)-thiophene-4'(5'H),3''(4''H)-[2H]quinolizine]-4,4''-diol,6,6''-di-3-furanyldodecahydro-9,9''-dimethyl-, [3S-[3a(3''R*,4''S*,6''R*,9''S*,9''aR*),4b,6b,9a,9aa]]-; Nuphlein; Nuphleine

Chemical Property of Dihydroxythiobinupharidine

Chemical Property:

• Boiling Point: 667.3±55.0 °C(Predicted)
• PKA: 13.42±0.70(Predicted)
• Density: 1.30±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

6,6′-Dihydroxythiobinupharidine ≥95% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Dihydroxythiobinupharidine

There total 5 articles about Dihydroxythiobinupharidine 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: 77.0%

C32H40N4O2S → 6,6'-dihydroxythionuphlutine B (30343-70-5,30343-71-6,51153-11-8,58846-67-6)

Guidance literature:

With silver nitrate; In water; acetonitrile; at 45 ℃;

DOI:10.1002/anie.201503934

Reference yield:

4-(furan-3-yl)-1-methyl-7-methyleneoctahydro-2H-quinolizine (60161-30-0) → 6,6'-dihydroxythionuphlutine B (30343-70-5,30343-71-6,51153-11-8,58846-67-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C

2.1: dichloromethane / 2 h / 0 °C

3.1: acetonitrile / 3 h / 20 °C

4.1: indium(III) triflate; 2,6-bis[(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazolin-2-yl]pyridine / dichloromethane / 0.08 h / 20 °C / Molecular sieve

4.2: 8 h / 20 °C / Molecular sieve

5.1: silver nitrate / acetonitrile; water / 45 °C

With indium(III) triflate; 2,6-bis[(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazolin-2-yl]pyridine; silver nitrate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; water; acetonitrile;

DOI:10.1002/anie.201503934

Reference yield:

C15H21NO2 → 6,6'-dihydroxythionuphlutine B (30343-70-5,30343-71-6,51153-11-8,58846-67-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dichloromethane / 2 h / 0 °C

2.1: acetonitrile / 3 h / 20 °C

3.1: indium(III) triflate; 2,6-bis[(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazolin-2-yl]pyridine / dichloromethane / 0.08 h / 20 °C / Molecular sieve

3.2: 8 h / 20 °C / Molecular sieve

4.1: silver nitrate / acetonitrile; water / 45 °C

With indium(III) triflate; 2,6-bis[(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazolin-2-yl]pyridine; silver nitrate; In dichloromethane; water; acetonitrile;

DOI:10.1002/anie.201503934

upstream raw materials:

4-(furan-3-yl)-1-methyl-7-methyleneoctahydro-2H-quinolizine

C₁₅H₂₀NO⁽¹⁺⁾*C₂F₃O₂^(1-)

Downstream raw materials:

thiobinupharidine

Refernces

• 1、 Yoshikawa, Masayuki,Murakami, Toshiyuki,Wakao, Shuji,Ishikado, Atsushi,Murakami, Nobutoshi,Yamahara, Johji,Matsuda, Hisashi. "Crude drugs from aquatic plants. VI. On the alkaloid constituents of Chinese Nupharis Rhizoma, the dried rhizoma of Nuphar pumilum (TIMM.) DC. (Nymphaceae) : Structures and rearrangement reaction of thiohemiaminal type nuphar alkaloids". . p. 1815 - 1824. Retrieved 2007/10/03.