(5S,6S)-5-(3,4,5-Trimethoxy-phenyl)-8-trimethylsilanyloxy-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid ethyl ester

Base Information

• Chemical Name: (5S,6S)-5-(3,4,5-Trimethoxy-phenyl)-8-trimethylsilanyloxy-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid ethyl ester
• CAS No.: 112026-12-7
• Molecular Formula: C₂₆H₃₂O₈Si
• Molecular Weight: 500.621
• Mol file: 112026-12-7.mol

Synonyms:

Chemical Property of (5S,6S)-5-(3,4,5-Trimethoxy-phenyl)-8-trimethylsilanyloxy-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,6S)-5-(3,4,5-Trimethoxy-phenyl)-8-trimethylsilanyloxy-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid ethyl ester

There total 3 articles about (5S,6S)-5-(3,4,5-Trimethoxy-phenyl)-8-trimethylsilanyloxy-5,6-dihydro-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:

trimethylsilyl iodide (16029-98-4) + (5S,6R)-8-Oxo-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid ethyl ester (75404-00-1,81649-61-8,106044-39-7,112026-11-6,114947-14-7) → (5S,6S)-5-(3,4,5-Trimethoxy-phenyl)-8-trimethylsilanyloxy-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid ethyl ester (112026-12-7)

Guidance literature:

With 1,1,1,3,3,3-hexamethyl-disilazane; at -20 ℃;

DOI:10.1016/S0040-4039(00)95770-8

Reference yield:

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + (5S,6R)-8-Oxo-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid ethyl ester (75404-00-1,81649-61-8,106044-39-7,112026-11-6,114947-14-7) → (5S,6S)-5-(3,4,5-Trimethoxy-phenyl)-8-trimethylsilanyloxy-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid ethyl ester (112026-12-7)

Guidance literature:

With triethylamine; at 3 ℃;

DOI:10.1016/S0040-4039(00)95770-8

Reference yield:

ethyl rel-(3R,4R)-6,7-methylenedioxy-1-oxo-4-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene-3-carboxylate (75404-00-1,81649-61-8,106044-39-7,112026-11-6,114947-14-7) → (5S,6S)-5-(3,4,5-Trimethoxy-phenyl)-8-trimethylsilanyloxy-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid ethyl ester (112026-12-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / 1.) 4 eq. LDA; 2.) aq. HCl / 2.) - 40 deg C

2: hexamethyldisilazane / -20 °C

With hydrogenchloride; 1,1,1,3,3,3-hexamethyl-disilazane; lithium diisopropyl amide;

DOI:10.1016/S0040-4039(00)95770-8

upstream raw materials:

trimethylsilyl iodide

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

trimethylsilyl trifluoromethanesulfonate

ethyl rel-(3R,4R)-6,7-methylenedioxy-1-oxo-4-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene-3-carboxylate

Downstream raw materials:

(+/-)-neopodophyllotoxin

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

C₂₉H₂₈O₈

9-hydroxy-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