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]dioxole-6-carboxylic acid

Base Information

Chemical Name: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]dioxole-6-carboxylic acid
CAS No.:642409-83-4
Molecular Formula:C₃₃H₅₀O₉Si₂
Molecular Weight:646.926
Hs Code.:

5-(<i>tert</i>-butyl-dimethyl-silanyloxy)-8-[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]dioxole-6-carboxylic acid

Synonyms: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]dioxole-6-carboxylic acid

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Chemical Property of 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]dioxole-6-carboxylic acid

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Technology Process of 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]dioxole-6-carboxylic acid

There total 7 articles about 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]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: 97.0%

: 642409-82-3
5-(tert-butyl-dimethyl-silanyloxy)-8-[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]dioxole-6-carboxylic acid

: 642409-83-4
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]dioxole-6-carboxylic acid

Guidance literature:: With lithium triethylborohydride; In tetrahydrofuran; at 0 ℃; for 1h;
DOI:10.1016/j.bmcl.2003.08.044

Reference yield:

: 6559-91-7
4'-demethylepipodophyllotoxin

: 642409-83-4
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]dioxole-6-carboxylic acid

Guidance literature:: Multi-step reaction with 6 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

4: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.83 h / 20 °C

5: 82 percent / aq. NaClO₂; NH₂SO₃H / 2-methyl-propan-2-ol / 1 h / 20 °C

6: 97 percent / LiEt₃BH / tetrahydrofuran / 1 h / 0 °C

With 2,6-dimethylpyridine; dmap; sodium chlorite; lithium aluminium tetrahydride; aminosulfonic acid; lithium triethylborohydride; Dess-Martin periodane; triethylamine; In tetrahydrofuran; dichloromethane; tert-butyl alcohol; 4: Dess-Martin oxidation;
DOI:10.1016/j.bmcl.2003.08.044

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 642409-83-4
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]dioxole-6-carboxylic acid

Guidance literature:: Multi-step reaction with 6 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

4: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.83 h / 20 °C

5: 82 percent / aq. NaClO₂; NH₂SO₃H / 2-methyl-propan-2-ol / 1 h / 20 °C

6: 97 percent / LiEt₃BH / tetrahydrofuran / 1 h / 0 °C

With 2,6-dimethylpyridine; dmap; sodium chlorite; lithium aluminium tetrahydride; aminosulfonic acid; lithium triethylborohydride; Dess-Martin periodane; triethylamine; In tetrahydrofuran; dichloromethane; tert-butyl alcohol; 4: Dess-Martin oxidation;
DOI:10.1016/j.bmcl.2003.08.044