2,2-dimethyl-propionic acid 8-(tert-butyl-dimethyl-silanyloxy)-5-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-7-hydroxymethyl-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxol-6-ylmethyl ester

Base Information

Chemical Name:2,2-dimethyl-propionic acid 8-(tert-butyl-dimethyl-silanyloxy)-5-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-7-hydroxymethyl-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxol-6-ylmethyl ester
CAS No.:642409-78-7
Molecular Formula:C₃₈H₆₀O₉Si₂
Molecular Weight:717.06
Hs Code.:

2,2-dimethyl-propionic acid 8-(<i>tert</i>-butyl-dimethyl-silanyloxy)-5-[4-(<i>tert</i>-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-7-hydroxymethyl-5,6,7,8-tetrahydro-naphtho[2,3-<i>d</i>][1,3]dioxol-6-ylmethyl ester

Synonyms:2,2-dimethyl-propionic acid 8-(tert-butyl-dimethyl-silanyloxy)-5-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-7-hydroxymethyl-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxol-6-ylmethyl ester

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Chemical Property of 2,2-dimethyl-propionic acid 8-(tert-butyl-dimethyl-silanyloxy)-5-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-7-hydroxymethyl-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxol-6-ylmethyl ester

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Technology Process of 2,2-dimethyl-propionic acid 8-(tert-butyl-dimethyl-silanyloxy)-5-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-7-hydroxymethyl-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxol-6-ylmethyl ester

There total 4 articles about 2,2-dimethyl-propionic acid 8-(tert-butyl-dimethyl-silanyloxy)-5-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-7-hydroxymethyl-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxol-6-ylmethyl 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: 65.0%

: 3282-30-2
pivaloyl chloride

: 153230-77-4
4,4'-bis(tert-butyldimethylsilyl)-4'-O-demethylepipodophyllol

: 642409-78-7
2,2-dimethyl-propionic acid 8-(tert-butyl-dimethyl-silanyloxy)-5-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-7-hydroxymethyl-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxol-6-ylmethyl ester

: 642409-77-6
2,2-dimethyl-propionic acid 5-(tert-butyl-dimethyl-silanyloxy)-8-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-7-hydroxymethyl-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxol-6-ylmethyl ester

: 2,2-dimethyl-propionic acid 8-(tert-butyl-dimethyl-silanyloxy)-5-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-7-(2,2-dimethyl-propionyloxymethyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxol-6-ylmethyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 0.666667h;
DOI:10.1016/j.bmcl.2003.08.044

Reference yield:

: 153230-70-7
4,4'-bis-O-(dimethyl-tert-butylsilyl)-4'-O-demethylepipodophyllotoxin

: 642409-78-7
2,2-dimethyl-propionic acid 8-(tert-butyl-dimethyl-silanyloxy)-5-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-7-hydroxymethyl-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxol-6-ylmethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 92 percent / LAH / tetrahydrofuran / 0.5 h / 0 - 20 °C

2: 27 percent / 4-DMAP; Et₃N / CH₂Cl₂ / 2 h / 20 °C

With dmap; lithium aluminium tetrahydride; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tet.2004.01.017

Reference yield:

: 6559-91-7
4'-demethylepipodophyllotoxin

: 642409-78-7
2,2-dimethyl-propionic acid 8-(tert-butyl-dimethyl-silanyloxy)-5-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-7-hydroxymethyl-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxol-6-ylmethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 81 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

2: 92 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 - 20 °C

3: 27 percent / Et₃N; 4-DMAP / CH₂Cl₂ / 0.67 h / 20 °C

With 2,6-dimethylpyridine; dmap; lithium aluminium tetrahydride; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.bmcl.2003.08.044