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

Base Information

• Chemical Name: 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
• CAS No.: 642409-89-0
• Molecular Formula: C₄₁H₄₀Cl₂O₁₇
• Molecular Weight: 875.664

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 8 articles about 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 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: 40.0%

Chloro-acetic acid (2R,4aR,6S,7R,8S,8aR)-7-(2-chloro-acetoxy)-2-methyl-6-trimethylsilanyloxy-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester + 11-oxo-13-deoxo-4'-benzyloxycarbonyl-4'-demethylepipodophyllotoxin (642409-85-6) → Carbonic acid benzyl ester 2,6-dimethoxy-4-((5R,5aR)-8-oxo-5,5a,6,8-tetrahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-phenyl ester + 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 (642409-89-0)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -60 - -10 ℃; for 5h;

DOI:10.1016/j.bmcl.2003.08.044

Reference yield:

4'-demethylepipodophyllotoxin (6559-91-7) → 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 (642409-89-0)

Guidance literature:

Multi-step reaction with 10 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

8: 80 percent / TBAF / tetrahydrofuran / 4 h / 20 °C

9: 85 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

10: 40 percent / BF₃*Et₂O / CH₂Cl₂ / 5 h / -60 - -10 °C

With 2,6-dimethylpyridine; dmap; sodium chlorite; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; aminosulfonic acid; tetrabutyl ammonium fluoride; lithium triethylborohydride; Dess-Martin periodane; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; tert-butyl alcohol; 4: Dess-Martin oxidation / 10: Kuhn-like coupling;

DOI:10.1016/j.bmcl.2003.08.044

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → 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 (642409-89-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

2: 40 percent / BF₃*Et₂O / CH₂Cl₂ / 5 h / -60 - -10 °C

With boron trifluoride diethyl etherate; triethylamine; In dichloromethane; 2: Kuhn-like coupling;

DOI:10.1016/j.bmcl.2003.08.044

upstream raw materials:

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

4'-demethylepipodophyllotoxin

benzyl chloroformate

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

Downstream raw materials:

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

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