(5aS,8aS,9R)-5a-Hydroxymethyl-9-(3,4,5-trimethoxy-phenyl)-5a,6,8a,9-tetrahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5,8-dione

Base Information

• Chemical Name: (5aS,8aS,9R)-5a-Hydroxymethyl-9-(3,4,5-trimethoxy-phenyl)-5a,6,8a,9-tetrahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5,8-dione
• CAS No.: 64897-39-8
• Molecular Formula: C₂₃H₂₂O₉
• Molecular Weight: 442.422
• Mol file: 64897-39-8.mol

Synonyms:

Chemical Property of (5aS,8aS,9R)-5a-Hydroxymethyl-9-(3,4,5-trimethoxy-phenyl)-5a,6,8a,9-tetrahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5,8-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5aS,8aS,9R)-5a-Hydroxymethyl-9-(3,4,5-trimethoxy-phenyl)-5a,6,8a,9-tetrahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5,8-dione

There total 6 articles about (5aS,8aS,9R)-5a-Hydroxymethyl-9-(3,4,5-trimethoxy-phenyl)-5a,6,8a,9-tetrahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5,8-dione 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%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 1,2,3,4-tetrahydro-6,7-methylenedioxy-4-oxo-1-(3,4,5-trimethoxyphenyl)naphthalene-2-carboxylic acid (64897-38-7,114381-03-2) → 3-hydroxymethylpicropodophyllon (64897-39-8,117179-02-9)

Guidance literature:

With sodium hydroxide; for 30h; Ambient temperature;

DOI:10.1039/P19820000271

Reference yield:

diethyl 8-oxo-5-(3,4,5-trimethoxyphenyl)-7,8-dihydronaphtho-[2,3-d][1,3]dioxole-6,6(5H)-dicarboxylate (64897-37-6) → (5aS,8aS,9R)-5a-Hydroxymethyl-9-(3,4,5-trimethoxy-phenyl)-5a,6,8a,9-tetrahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5,8-dione (64897-39-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 0.31 M KOH / ethanol / 2.5 h / Heating

2: decarboxylation

3: hydroxymethylation

With potassium hydroxide; In ethanol;

DOI:10.1021/jo00326a056

Reference yield:

4-Methoxy-2,2-dicarbethoxy-6,7-methylenedioxy-1-(3',4',5'-trimethoxyphenyl)tetralin (81701-18-0) → (5aS,8aS,9R)-5a-Hydroxymethyl-9-(3,4,5-trimethoxy-phenyl)-5a,6,8a,9-tetrahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5,8-dione (64897-39-8)

Guidance literature:

Multi-step reaction with 5 steps

1: CF₃CO₂H / 0.08 h / -10 °C

2: 86 percent / C₅H₅N*HCl*CrO₃ / CH₂Cl₂ / 1 h / Ambient temperature

3: 0.31 M KOH / ethanol / 2.5 h / Heating

4: decarboxylation

5: hydroxymethylation

With potassium hydroxide; Pyr*CrO₃*HCl; trifluoroacetic acid; In ethanol; dichloromethane;

DOI:10.1021/jo00326a056

upstream raw materials:

formaldehyd

1,2,3,4-tetrahydro-6,7-methylenedioxy-4-oxo-1-(3,4,5-trimethoxyphenyl)naphthalene-2-carboxylic acid

5-Benzo[1,3]dioxol-5-yl-5-hydroxy-2-(3,4,5-trimethoxy-phenyl)-tetrahydro-furan-3-carboxylic acid ethyl ester

diethyl 8-oxo-5-(3,4,5-trimethoxyphenyl)-7,8-dihydronaphtho-[2,3-d][1,3]dioxole-6,6(5H)-dicarboxylate

Downstream raw materials:

(5α,5aα,8aβ)-5,5a,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)furo<3',4':6,7>naphtho<2,3-d>-1,3-dioxole-6(5aH),9-(8aH)-dione