(2R,6S)-2-acetoxymethyl-4-methylene-6-[(4S,6R,8S)-6,8,10-triacetoxy-4-benzyloxy-3,3-dimethyl-2-oxodecyl]tetrahydropyran

Base Information

• Chemical Name: (2R,6S)-2-acetoxymethyl-4-methylene-6-[(4S,6R,8S)-6,8,10-triacetoxy-4-benzyloxy-3,3-dimethyl-2-oxodecyl]tetrahydropyran
• CAS No.: 470470-81-6
• Molecular Formula: C₃₄H₄₈O₁₁
• Molecular Weight: 632.749

Synonyms:(2R,6S)-2-acetoxymethyl-4-methylene-6-[(4S,6R,8S)-6,8,10-triacetoxy-4-benzyloxy-3,3-dimethyl-2-oxodecyl]tetrahydropyran

Chemical Property of (2R,6S)-2-acetoxymethyl-4-methylene-6-[(4S,6R,8S)-6,8,10-triacetoxy-4-benzyloxy-3,3-dimethyl-2-oxodecyl]tetrahydropyran

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of (2R,6S)-2-acetoxymethyl-4-methylene-6-[(4S,6R,8S)-6,8,10-triacetoxy-4-benzyloxy-3,3-dimethyl-2-oxodecyl]tetrahydropyran

There total 14 articles about (2R,6S)-2-acetoxymethyl-4-methylene-6-[(4S,6R,8S)-6,8,10-triacetoxy-4-benzyloxy-3,3-dimethyl-2-oxodecyl]tetrahydropyran 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%

(3S,5R,7S,15R,10E)-7-benzyloxy-1,15,16-tris-(tert-butyldimethylsilyloxy)-3,5-dihydroxy-8,8-dimethyl-3,5-O-isopropylidene-13-((E)-trimethylsilylmethylidene)hexadec-10-en-9-one (1352746-52-1) + acetic anhydride (108-24-7) → (2R,6S)-2-acetoxymethyl-4-methylene-6-[(4S,6R,8S)-6,8,10-triacetoxy-4-benzyloxy-3,3-dimethyl-2-oxodecyl]tetrahydropyran (470470-81-6)

Guidance literature:

(3S,5R,7S,15R,10E)-7-benzyloxy-1,15,16-tris-(tert-butyldimethylsilyloxy)-3,5-dihydroxy-8,8-dimethyl-3,5-O-isopropylidene-13-((E)-trimethylsilylmethylidene)hexadec-10-en-9-one; With hydrogen fluoride; In water; acetonitrile; at 20 ℃; for 18h;

acetic anhydride; With pyridine; dmap; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1016/j.tet.2011.09.064

Reference yield:

(5S,7S)-7-benzyloxy-9-tert-butyldimethylsilyloxy-1-tert-butyldiphenylsilyloxy-5-hydroxy-8,8-dimethylnonan-3-one (470470-80-5) → (2R,6S)-2-acetoxymethyl-4-methylene-6-[(4S,6R,8S)-6,8,10-triacetoxy-4-benzyloxy-3,3-dimethyl-2-oxodecyl]tetrahydropyran (470470-81-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: lithium tri-t-butoxyaluminum hydride; lithium iodide / tetrahydrofuran; diethyl ether / 18 h / -78 °C / Inert atmosphere

2.1: pyridinium p-toluenesulfonate / 18 h / 20 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere

4.1: 1H-imidazole / dichloromethane / 0 °C

5.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

6.1: tetrahydrofuran / -78 - 20 °C / Inert atmosphere

7.1: Dess-Martin periodane / dichloromethane / 0.33 h / 20 °C / Inert atmosphere

8.1: zinc(II) iodide / dichloromethane / 48 h / 20 °C / Molecular sieve; Inert atmosphere

9.1: hydrogen fluoride / water; acetonitrile / 18 h / 20 °C

9.2: 18 h / 20 °C / Inert atmosphere

With 1H-imidazole; hydrogen fluoride; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; Dess-Martin periodane; lithium tri-t-butoxyaluminum hydride; zinc(II) iodide; lithium iodide; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetonitrile;

DOI:10.1016/j.tet.2011.09.064

Reference yield:

(3S,5R,7S)-7-benzyloxy-8,8-dimethyl-3,5-O-isopropylidenenonane-1,3,5,9-tetraol (1352746-48-5) → (2R,6S)-2-acetoxymethyl-4-methylene-6-[(4S,6R,8S)-6,8,10-triacetoxy-4-benzyloxy-3,3-dimethyl-2-oxodecyl]tetrahydropyran (470470-81-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 1H-imidazole / dichloromethane / 0 °C

2.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

3.1: tetrahydrofuran / -78 - 20 °C / Inert atmosphere

4.1: Dess-Martin periodane / dichloromethane / 0.33 h / 20 °C / Inert atmosphere

5.1: zinc(II) iodide / dichloromethane / 48 h / 20 °C / Molecular sieve; Inert atmosphere

6.1: hydrogen fluoride / water; acetonitrile / 18 h / 20 °C

6.2: 18 h / 20 °C / Inert atmosphere

With 1H-imidazole; hydrogen fluoride; Dess-Martin periodane; zinc(II) iodide; In tetrahydrofuran; dichloromethane; water; acetonitrile;

DOI:10.1016/j.tet.2011.09.064

upstream raw materials:

(5S,7S)-7-benzyloxy-9-tert-butyldimethylsilyloxy-1-tert-butyldiphenylsilyloxy-5-hydroxy-8,8-dimethylnonan-3-one

(3S,5R,7S)-7-benzyloxy-9-tert-butyldimethylsilyloxy-1-tert-butyldiphenylsilyloxy-8,8-dimethylnonane-3,5-diol

(3S,5R,7S)-7-benzyloxy-9-tert-butyldimethylsilyloxy-1-tert-butyldiphenylsilyloxy-8,8-dimethyl-3,5-O-isopropylidenenonane-3,5-diol

(3S,5R,7S)-7-benzyloxy-8,8-dimethyl-3,5-O-isopropylidenenonane-1,3,5,9-tetraol

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