(2aR,6bβ,7aβ,7bα,8R)-Octahydro-2aα,6aα-dihydroxy-7cα-methyl-8-(1-methylethenyl)-3α,6α-methano-2,4,7-trioxacyclopenta[cd]cycloprop[a]azulen-5(6H)-one

Base Information

• Chemical Name: (2aR,6bβ,7aβ,7bα,8R)-Octahydro-2aα,6aα-dihydroxy-7cα-methyl-8-(1-methylethenyl)-3α,6α-methano-2,4,7-trioxacyclopenta[cd]cycloprop[a]azulen-5(6H)-one
• CAS No.: 94451-13-5
• Molecular Formula: C₁₅H₁₈O₆
• Molecular Weight: 294.304
• Mol file: 94451-13-5.mol

Synonyms:(+)-asteromurin;

Chemical Property of (2aR,6bβ,7aβ,7bα,8R)-Octahydro-2aα,6aα-dihydroxy-7cα-methyl-8-(1-methylethenyl)-3α,6α-methano-2,4,7-trioxacyclopenta[cd]cycloprop[a]azulen-5(6H)-one

Chemical Property:

• PSA: 88.52000
• LogP: -0.41270

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2aR,6bβ,7aβ,7bα,8R)-Octahydro-2aα,6aα-dihydroxy-7cα-methyl-8-(1-methylethenyl)-3α,6α-methano-2,4,7-trioxacyclopenta[cd]cycloprop[a]azulen-5(6H)-one

There total 11 articles about (2aR,6bβ,7aβ,7bα,8R)-Octahydro-2aα,6aα-dihydroxy-7cα-methyl-8-(1-methylethenyl)-3α,6α-methano-2,4,7-trioxacyclopenta[cd]cycloprop[a]azulen-5(6H)-one 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: 94.0%

C18H18BrCl3O8 (94472-22-7) → (+)-asteromurin A (94451-13-5)

Guidance literature:

With ammonium chloride; zinc; In ethanol; for 1h; Heating;

DOI:10.1016/S0040-4020(01)88159-X

Reference yield:

C17H21BrO5 (93177-99-2) → (+)-asteromurin A (94451-13-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) B₂H₆; 2.) 3M NaOH, 30percent aq. H₂O₂ / 1.) THF, RT, 4 h; 2.) 55 deg C, 1 h

2: 60 percent / pyridine / 1.5 h / -25 °C

3: 72 percent / ruthenium tetraoxide (RuCl₃-NaIO₄), phosphate buffer / CCl₄; acetonitrile / 43 h / 40 °C / pH=7

4: 94 percent / zinc, NH₄Cl / ethanol / 1 h / Heating

With pyridine; sodium hydroxide; phosphate buffer; ruthenium tetroxide; dihydrogen peroxide; ammonium chloride; diborane; zinc; In tetrachloromethane; ethanol; acetonitrile;

DOI:10.1246/cl.1984.1763

Reference yield:

C15H21BrO5 (94450-96-1) → (+)-asteromurin A (94451-13-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent / pyridine / 1.5 h / -25 °C

2: 72 percent / ruthenium tetraoxide (RuCl₃-NaIO₄), phosphate buffer / CCl₄; acetonitrile / 43 h / 40 °C / pH=7

3: 94 percent / zinc, NH₄Cl / ethanol / 1 h / Heating

With pyridine; phosphate buffer; ruthenium tetroxide; ammonium chloride; zinc; In tetrachloromethane; ethanol; acetonitrile;

DOI:10.1246/cl.1984.1763

upstream raw materials:

C₁₈H₁₈BrCl₃O₈

C₁₇H₂₁BrO₅

C₁₅H₂₁BrO₅

C₁₈H₂₂BrCl₃O₇

Refernces

• 1、 Wakamatsu,Kigoshi,Niiyama,et al.. "Stereocontrolled total synthesis of (+)-tutin and (+)-asteromurin A, toxic picrotoxane sesquiterpenes". . p. 5551 - 5558. Retrieved 2007/10/02.