8-(tert-butyl-dimethyl-silanyloxy)-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid

Base Information

• Chemical Name: 8-(tert-butyl-dimethyl-silanyloxy)-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid
• CAS No.: 303958-06-7
• Molecular Formula: C₂₈H₃₈O₉Si
• Molecular Weight: 546.69
• Mol file: 303958-06-7.mol

Synonyms:8-(tert-butyl-dimethyl-silanyloxy)-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid

Chemical Property of 8-(tert-butyl-dimethyl-silanyloxy)-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-(tert-butyl-dimethyl-silanyloxy)-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid

There total 3 articles about 8-(tert-butyl-dimethyl-silanyloxy)-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid 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: 100.0%

(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 (112711-16-7) → 8-(tert-butyl-dimethyl-silanyloxy)-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid (303958-06-7)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 0 ℃;

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

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → 8-(tert-butyl-dimethyl-silanyloxy)-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid (303958-06-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

2: 100 percent / aq. NaOH / tetrahydrofuran / 0 °C

With 2,6-dimethylpyridine; sodium hydroxide; In tetrahydrofuran; dichloromethane; 1: silylation / 2: Hydrolysis;

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

Reference yield:

podofilox (518-28-5) → 8-(tert-butyl-dimethyl-silanyloxy)-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid (303958-06-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

2: 100 percent / aq. NaOH / tetrahydrofuran / 0 °C

With 2,6-dimethylpyridine; sodium hydroxide; In tetrahydrofuran; dichloromethane; 1: silylation / 2: Hydrolysis;

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

upstream raw materials:

(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

t-butyldimethylsiyl triflate

podofilox

Downstream raw materials:

(5R,6S,7S,8R)-8-(tert-Butyl-dimethyl-silanyloxy)-7-((E)-2-methoxy-vinyl)-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester

8-(tert-butyl-dimethyl-silanyloxy)-5-(3,4,5-trimethoxy-phenyl)-7-vinyl-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester

8-(tert-butyl-dimethyl-silanyloxy)-7-formyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester

(5R,6S,7S,8S)-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 methyl ester