SECOLOGANIN ETHYLENE ACETAL TETRAACETATE

Base Information

• Chemical Name: SECOLOGANIN ETHYLENE ACETAL TETRAACETATE
• CAS No.: 79409-46-4
• Molecular Formula: C27H36O15
• Molecular Weight: 600.574
• Mol file: 79409-46-4.mol

Synonyms:SECOLOGANIN ETHYLENE ACETAL TETRAACETATE

Chemical Property of SECOLOGANIN ETHYLENE ACETAL TETRAACETATE

Chemical Property:

• Vapor Pressure: 6.83E-16mmHg at 25°C
• Boiling Point: 632.2°C at 760 mmHg
• Flash Point: 263.8°C
• PSA: 177.65000
• Density: 1.32g/cm³
• LogP: 0.68070

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of SECOLOGANIN ETHYLENE ACETAL TETRAACETATE

There total 4 articles about SECOLOGANIN ETHYLENE ACETAL TETRAACETATE 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: 91.0%

acetic anhydride (108-24-7) + Methyl (2S,3R,4S)-4-(1,3-Dioxolan-2-ylmethyl)-2-(β-D-glucopyranosyloxy)-3,4-dihydro-3-vinyl-2H-pyran-5-carboxylate (79409-45-3) → Methyl (2S,3R,4S)-4-(1,3-Dioxolan-2-ylmethyl)-3,4-dihydro-2-(2,3,4,6-tetraacetyl-β-D-glucopyranosyloxy)-3-vinyl-2H-pyran-5-carboxylate (79409-46-4)

Guidance literature:

In pyridine; at 20 ℃; for 24h;

Reference yield:

secologanin (19351-63-4) → Methyl (2S,3R,4S)-4-(1,3-Dioxolan-2-ylmethyl)-3,4-dihydro-2-(2,3,4,6-tetraacetyl-β-D-glucopyranosyloxy)-3-vinyl-2H-pyran-5-carboxylate (79409-46-4)

Guidance literature:

Multi-step reaction with 2 steps

1: Dowex 50WX₂ H⁽¹⁺⁾

2: pyridine

With pyridine; Dowex 50WX₂ H⁽¹⁺⁾;

DOI:10.1016/j.tetlet.2006.01.009

Reference yield:

O,O,O,O-tetraacetylsecologaninn (27856-66-2) + ethylene glycol (107-21-1) → Methyl (2S,3R,4S)-4-(1,3-Dioxolan-2-ylmethyl)-3,4-dihydro-2-(2,3,4,6-tetraacetyl-β-D-glucopyranosyloxy)-3-vinyl-2H-pyran-5-carboxylate (79409-46-4)

Guidance literature:

With trifluoroacetic acid; In tetrahydrofuran; for 1h; Heating;

DOI:10.1039/c39910000825

upstream raw materials:

methyltriphenylphosphonium iodide

(4S,5S,6S)-4-[1,3]Dioxolan-2-ylmethyl-5-formyl-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester

acetic anhydride

Methyl (2S,3R,4S)-4-(1,3-Dioxolan-2-ylmethyl)-2-(β-D-glucopyranosyloxy)-3,4-dihydro-3-vinyl-2H-pyran-5-carboxylate

Downstream raw materials:

(4aS,5R,6S)-3-Methoxy-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-5-vinyl-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-1-one

β-yohimbine

(+)-yohimbinone

Yohimbine

Refernces

• 1、 Brown, Richard T.,Pratt, Simon B.,Richards, Paul. "Enantiospecific synthesis of (-)-3-iso-19,20-dehydro-β-yohimbine from secologanin: A route to normal and pseudo stereoisomers of yohimbine". . p. 5627 - 5630. Retrieved 2007/10/03.
• 2、 Brown, Richard T.,Dauda, Bukar E. N.,Santos, Cid A. M.. "Hydrolysis and Selective Reduction with Yeast: Enantiospecific Synthesis of Antirhine from Secologanin". . p. 825 - 826. Retrieved 2007/10/02.