6H-1,3-Dioxolo[6,7]naphtho[2,3-c]pyran-6-one,5,5a,8,9,9a,10-hexahydro-10-hydroxy-5-(3,4,- 5-trimethoxyphenyl)-,(5R,5aS,9aS,10R)-

Base Information

• Chemical Name: 6H-1,3-Dioxolo[6,7]naphtho[2,3-c]pyran-6-one,5,5a,8,9,9a,10-hexahydro-10-hydroxy-5-(3,4,- 5-trimethoxyphenyl)-,(5R,5aS,9aS,10R)-
• CAS No.: 98369-20-1
• Molecular Formula: C₂₃H₂₄O₈
• Molecular Weight: 428.439
• Mol file: 98369-20-1.mol

Synonyms:

Chemical Property of 6H-1,3-Dioxolo[6,7]naphtho[2,3-c]pyran-6-one,5,5a,8,9,9a,10-hexahydro-10-hydroxy-5-(3,4,- 5-trimethoxyphenyl)-,(5R,5aS,9aS,10R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 6H-1,3-Dioxolo[6,7]naphtho[2,3-c]pyran-6-one,5,5a,8,9,9a,10-hexahydro-10-hydroxy-5-(3,4,- 5-trimethoxyphenyl)-,(5R,5aS,9aS,10R)-

There total 15 articles about 6H-1,3-Dioxolo[6,7]naphtho[2,3-c]pyran-6-one,5,5a,8,9,9a,10-hexahydro-10-hydroxy-5-(3,4,- 5-trimethoxyphenyl)-,(5R,5aS,9aS,10R)- 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: 84.0%

(5R,5aS,9aS,10R)-10-Hydroxy-5-(3,4,5-trimethoxy-phenyl)-5,9,9a,10-tetrahydro-5aH-1,3,7-trioxa-cyclopenta[b]anthracene-6,8-dione (101766-79-4) → picropodophyllin homolactone (98369-20-1)

Guidance literature:

With sodium amalgam; In ethanol; for 18h; Ambient temperature;

Reference yield:

(5R,6S,7S,8R)-8-Hydroxy-7-(2-hydroxy-ethyl)-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid → picropodophyllin homolactone (98369-20-1)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 25 ℃;

DOI:10.1016/S0040-4039(00)01136-9

Reference yield:

podofilox (518-28-5) → picropodophyllin homolactone (98369-20-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

2.1: 100 percent / aq. NaOH / tetrahydrofuran / 0 °C

3.1: Dess-Martin periodinane / CH₂Cl₂ / 25 °C

4.1: K₂CO₃ / acetone / 25 °C

5.1: 76 percent / n-BuLi / tetrahydrofuran / -78 °C

6.1: 92 percent / TBAF / tetrahydrofuran / 25 °C

7.1: 9-BBN / tetrahydrofuran / 25 °C

7.2: 61 percent / aq. H₂O₂ / aq. phosphate buffer; methanol / 25 °C / pH 7

8.1: aq. NaOH / tetrahydrofuran / 0 °C

9.1: DCC; 4-DMAP / tetrahydrofuran / 25 °C

With 2,6-dimethylpyridine; dmap; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; tetrabutyl ammonium fluoride; potassium carbonate; Dess-Martin periodane; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; acetone; 1.1: silylation / 2.1: Hydrolysis / 3.1: Oxidation / 4.1: oxidative esterification / 5.1: Wittig methylenation / 6.1: desilylation / 7.1: hydroboration / 7.2: Hydrolysis / 8.1: Hydrolysis / 9.1: Esterification;

DOI:10.1016/S0040-4039(00)01136-9

upstream raw materials:

(5R,5aS,9aS,10R)-10-Hydroxy-5-(3,4,5-trimethoxy-phenyl)-5,9,9a,10-tetrahydro-5aH-1,3,7-trioxa-cyclopenta[b]anthracene-6,8-dione

picropodophyllotoxin

(5R,5aR,8aR,9R)-9-((tert-butyldimethylsilyl)oxy)-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one

(+)-4-O-(tert-butyldimethylsilyl)picropodophyllin