(5S,6R,7R,8R)-8-Hydroxy-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid ethyl ester

Base Information

• Chemical Name: (5S,6R,7R,8R)-8-Hydroxy-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid ethyl ester
• CAS No.: 158110-15-7
• Molecular Formula: C₂₄H₂₈O₉
• Molecular Weight: 460.481

Synonyms:(5S,6R,7R,8R)-8-Hydroxy-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid ethyl ester

Chemical Property of (5S,6R,7R,8R)-8-Hydroxy-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid ethyl ester

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Technology Process of (5S,6R,7R,8R)-8-Hydroxy-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid ethyl ester

There total 5 articles about (5S,6R,7R,8R)-8-Hydroxy-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid ethyl ester 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: 52.0%

10-menthyloxyisopicropodophyllin (157918-95-1) → (5S,6R,7R,8R)-8-Hydroxy-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid ethyl ester (158110-15-7) + (5S,5aR,8R,8aS,9R)-9-Hydroxy-8-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-5-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one

Guidance literature:

With sodium tetrahydroborate; In ethanol; for 20h;

DOI:10.1016/S0957-4166(00)86243-6

Reference yield: 44.0%

ethanol (64-17-5) + 10-menthyloxyisopicropodophyllin (157918-95-1) → (5S,6R,7R,8R)-8-Hydroxy-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid ethyl ester (158110-15-7) + (5S,5aR,8R,8aS,9R)-9-Hydroxy-8-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-5-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one

Guidance literature:

With sodium tetrahydroborate; for 20h;

DOI:10.1016/S0957-4166(00)86243-6

Reference yield: 41.0%

10-menthyloxyisopicropodophyllin (157918-95-1) → β-Apopicropodophyllin (157918-96-2) + (5S,6R,7R,8R)-8-Hydroxy-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid ethyl ester (158110-15-7)

Guidance literature:

With potassium hydroxide; sodium tetrahydroborate; In ethanol; at 0 ℃; for 2.75h;

DOI:10.1016/S0957-4166(00)86243-6

upstream raw materials:

ethanol

10-menthyloxyisopicropodophyllin

-3,4-methylenedioxybenzaldehyde dimethyl acetal

C₃₂H₃₈O₉

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