(1R,2R,3R,4'aα,7'β,9'aβ)-3-Acetoxymethylhexahydro-3-methyl-8'-methylene-1',9'-dioxospiro[cyclohexane-1,4'(3'H)-[1H-7,9a]methanocyclohepta[c]pyran]-2-carbaldehyde

Base Information

• Chemical Name: (1R,2R,3R,4'aα,7'β,9'aβ)-3-Acetoxymethylhexahydro-3-methyl-8'-methylene-1',9'-dioxospiro[cyclohexane-1,4'(3'H)-[1H-7,9a]methanocyclohepta[c]pyran]-2-carbaldehyde
• CAS No.: 39388-60-8
• Molecular Formula: C22H28O6
• Molecular Weight: 388.45412
• Mol file: 39388-60-8.mol

Synonyms:

Chemical Property of (1R,2R,3R,4'aα,7'β,9'aβ)-3-Acetoxymethylhexahydro-3-methyl-8'-methylene-1',9'-dioxospiro[cyclohexane-1,4'(3'H)-[1H-7,9a]methanocyclohepta[c]pyran]-2-carbaldehyde

Chemical Property:

• Melting Point: 187 - 189 °C
• PSA: 86.74000
• LogP: 2.63960

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,3R,4'aα,7'β,9'aβ)-3-Acetoxymethylhexahydro-3-methyl-8'-methylene-1',9'-dioxospiro[cyclohexane-1,4'(3'H)-[1H-7,9a]methanocyclohepta[c]pyran]-2-carbaldehyde

There total 8 articles about (1R,2R,3R,4'aα,7'β,9'aβ)-3-Acetoxymethylhexahydro-3-methyl-8'-methylene-1',9'-dioxospiro[cyclohexane-1,4'(3'H)-[1H-7,9a]methanocyclohepta[c]pyran]-2-carbaldehyde 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: 65.0%

C22H30O6 → (-)-effusin (39388-60-8)

Guidance literature:

With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 2.33h; Inert atmosphere;

DOI:10.1021/jacs.9b03978

Reference yield:

C32H58O4Si2 → (-)-effusin (39388-60-8)

Guidance literature:

Multi-step reaction with 5 steps

1: selenium(IV) oxide; tert.-butylhydroperoxide / dichloromethane / 6 h / 20 °C / Inert atmosphere

2: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 3 h / 20 °C / Inert atmosphere

3: lithium tetrafluoroborate / water; acetonitrile / 7 h / 50 °C / Inert atmosphere

4: dmap; dicyclohexyl-carbodiimide / dichloromethane / 9.5 h / -10 °C / Inert atmosphere

5: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2.33 h / 20 °C / Inert atmosphere

With tert.-butylhydroperoxide; dmap; selenium(IV) oxide; lithium tetrafluoroborate; sodium hydrogencarbonate; Dess-Martin periodane; dicyclohexyl-carbodiimide; In dichloromethane; water; acetonitrile; 2: |Dess-Martin Oxidation / 4: |Steglich Esterification / 5: |Dess-Martin Oxidation;

DOI:10.1021/jacs.9b03978

Reference yield:

C32H58O5Si2 → (-)-effusin (39388-60-8)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 3 h / 20 °C / Inert atmosphere

2: lithium tetrafluoroborate / water; acetonitrile / 7 h / 50 °C / Inert atmosphere

3: dmap; dicyclohexyl-carbodiimide / dichloromethane / 9.5 h / -10 °C / Inert atmosphere

4: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2.33 h / 20 °C / Inert atmosphere

With dmap; lithium tetrafluoroborate; sodium hydrogencarbonate; Dess-Martin periodane; dicyclohexyl-carbodiimide; In dichloromethane; water; acetonitrile; 1: |Dess-Martin Oxidation / 3: |Steglich Esterification / 4: |Dess-Martin Oxidation;

DOI:10.1021/jacs.9b03978