5-(tert-butyl-dimethyl-silanyloxy)-9-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one

Base Information

• Chemical Name: 5-(tert-butyl-dimethyl-silanyloxy)-9-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one
• CAS No.: 642409-84-5
• Molecular Formula: C₃₃H₄₈O₈Si₂
• Molecular Weight: 628.91

Synonyms:5-(tert-butyl-dimethyl-silanyloxy)-9-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one

Chemical Property of 5-(tert-butyl-dimethyl-silanyloxy)-9-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of 5-(tert-butyl-dimethyl-silanyloxy)-9-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one

There total 7 articles about 5-(tert-butyl-dimethyl-silanyloxy)-9-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one 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: 83.0%

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 (642409-83-4) → 5-(tert-butyl-dimethyl-silanyloxy)-9-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one (642409-84-5)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.bmcl.2003.08.044

Reference yield:

4'-demethylepipodophyllotoxin (6559-91-7) → 5-(tert-butyl-dimethyl-silanyloxy)-9-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one (642409-84-5)

Guidance literature:

Multi-step reaction with 7 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

7: 83 percent / DCC; 4-DMAP / CH₂Cl₂ / 1 h / 20 °C

With 2,6-dimethylpyridine; dmap; sodium chlorite; lithium aluminium tetrahydride; aminosulfonic acid; lithium triethylborohydride; Dess-Martin periodane; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; tert-butyl alcohol; 4: Dess-Martin oxidation;

DOI:10.1016/j.bmcl.2003.08.044

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 5-(tert-butyl-dimethyl-silanyloxy)-9-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one (642409-84-5)

Guidance literature:

Multi-step reaction with 7 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

7: 83 percent / DCC; 4-DMAP / CH₂Cl₂ / 1 h / 20 °C

With 2,6-dimethylpyridine; dmap; sodium chlorite; lithium aluminium tetrahydride; aminosulfonic acid; lithium triethylborohydride; Dess-Martin periodane; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; tert-butyl alcohol; 4: Dess-Martin oxidation;

DOI:10.1016/j.bmcl.2003.08.044

upstream raw materials:

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

4'-demethylepipodophyllotoxin

tert-butyldimethylsilyl chloride

4,4'-bis(tert-butyldimethylsilyl)-4'-O-demethylepipodophyllol

Downstream raw materials:

chloro-acetic acid 6-[9-(4-benzyloxycarbonyloxy-3,5-dimethoxy-phenyl)-6-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yloxy]-8-chloroacetoxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Carbonic acid benzyl ester 4-[(5R,5aR,8aS,9S)-9-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-8-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl]-2,6-dimethoxy-phenyl ester

11-oxo-13-deoxo-4'-benzyloxycarbonyl-4'-demethylepipodophyllotoxin

11-oxo-13-deoxo-4'-demethylepipodophyllotoxin

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