methyl (6R,2Z,4E,8E)-10-{(2R,3S,6R,8R,10S)-10-tert-butyldimethylsilyloxy-3-methyl-2-(1-methylethyl)-1,7-dioxaspiro[5.5]undecan-8-yl}-2-[1-(2-trimethylsilylethoxycarbonyl)-2,3-dihydroxy-4-methoxy-5-methyl-cyclohexan-2-yl]-6,8-dimethyldeca-2,4,8-trienoate

Base Information

Chemical Name:methyl (6R,2Z,4E,8E)-10-{(2R,3S,6R,8R,10S)-10-tert-butyldimethylsilyloxy-3-methyl-2-(1-methylethyl)-1,7-dioxaspiro[5.5]undecan-8-yl}-2-[1-(2-trimethylsilylethoxycarbonyl)-2,3-dihydroxy-4-methoxy-5-methyl-cyclohexan-2-yl]-6,8-dimethyldeca-2,4,8-trienoate
CAS No.:871023-00-6
Molecular Formula:C₄₆H₈₂O₁₀Si₂
Molecular Weight:851.322
Hs Code.:

methyl (6R,2Z,4E,8E)-10-{(2R,3S,6R,8R,10S)-10-tert-butyldimethylsilyloxy-3-methyl-2-(1-methylethyl)-1,7-dioxaspiro[5.5]undecan-8-yl}-2-[1-(2-trimethylsilylethoxycarbonyl)-2,3-dihydroxy-4-methoxy-5-methyl-cyclohexan-2-yl]-6,8-dimethyldeca-2,4,8-trienoate

Synonyms:methyl (6R,2Z,4E,8E)-10-{(2R,3S,6R,8R,10S)-10-tert-butyldimethylsilyloxy-3-methyl-2-(1-methylethyl)-1,7-dioxaspiro[5.5]undecan-8-yl}-2-[1-(2-trimethylsilylethoxycarbonyl)-2,3-dihydroxy-4-methoxy-5-methyl-cyclohexan-2-yl]-6,8-dimethyldeca-2,4,8-trienoate

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Chemical Property of methyl (6R,2Z,4E,8E)-10-{(2R,3S,6R,8R,10S)-10-tert-butyldimethylsilyloxy-3-methyl-2-(1-methylethyl)-1,7-dioxaspiro[5.5]undecan-8-yl}-2-[1-(2-trimethylsilylethoxycarbonyl)-2,3-dihydroxy-4-methoxy-5-methyl-cyclohexan-2-yl]-6,8-dimethyldeca-2,4,8-trienoate

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Technology Process of methyl (6R,2Z,4E,8E)-10-{(2R,3S,6R,8R,10S)-10-tert-butyldimethylsilyloxy-3-methyl-2-(1-methylethyl)-1,7-dioxaspiro[5.5]undecan-8-yl}-2-[1-(2-trimethylsilylethoxycarbonyl)-2,3-dihydroxy-4-methoxy-5-methyl-cyclohexan-2-yl]-6,8-dimethyldeca-2,4,8-trienoate

There total 1 articles about methyl (6R,2Z,4E,8E)-10-{(2R,3S,6R,8R,10S)-10-tert-butyldimethylsilyloxy-3-methyl-2-(1-methylethyl)-1,7-dioxaspiro[5.5]undecan-8-yl}-2-[1-(2-trimethylsilylethoxycarbonyl)-2,3-dihydroxy-4-methoxy-5-methyl-cyclohexan-2-yl]-6,8-dimethyldeca-2,4,8-trienoate 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: 92.0%

: C₅₂H₉₆O₁₁Si₃

: 871023-00-6
methyl (6R,2Z,4E,8E)-10-{(2R,3S,6R,8R,10S)-10-tert-butyldimethylsilyloxy-3-methyl-2-(1-methylethyl)-1,7-dioxaspiro[5.5]undecan-8-yl}-2-[1-(2-trimethylsilylethoxycarbonyl)-2,3-dihydroxy-4-methoxy-5-methyl-cyclohexan-2-yl]-6,8-dimethyldeca-2,4,8-trienoate

Guidance literature:: With iodine; In benzene; for 1.5h; Irradiation;
DOI:10.1039/b508670a

Reference yield:

: 871023-00-6
methyl (6R,2Z,4E,8E)-10-{(2R,3S,6R,8R,10S)-10-tert-butyldimethylsilyloxy-3-methyl-2-(1-methylethyl)-1,7-dioxaspiro[5.5]undecan-8-yl}-2-[1-(2-trimethylsilylethoxycarbonyl)-2,3-dihydroxy-4-methoxy-5-methyl-cyclohexan-2-yl]-6,8-dimethyldeca-2,4,8-trienoate

: (4S,6R)-28-chloro-6-hydroxy-28-deoxa-3,4-dihydromilbemycin

Guidance literature:: Multi-step reaction with 5 steps

1.1: 98 percent / silica gel / CHCl₃ / 16 h

2.1: 78 percent / tetrabutylammonium fluoride / tetrahydrofuran / 10 h / 20 °C

3.1: 23 percent / DMAP; dicyclohexylcarbodiimide / CH₂Cl₂ / 16 h / 0 °C

4.1: 74 percent / DIBAL-H / toluene / 1 h / -78 °C

5.1: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.17 h / -78 °C

5.2: 100 percent / TsCl / tetrahydrofuran; hexamethylphosphoric acid triamide / 2.5 h / -78 - 0 °C

With dmap; tetrabutyl ammonium fluoride; silica gel; diisobutylaluminium hydride; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; chloroform; toluene;
DOI:10.1039/b508670a

Reference yield:

: 871023-00-6
methyl (6R,2Z,4E,8E)-10-{(2R,3S,6R,8R,10S)-10-tert-butyldimethylsilyloxy-3-methyl-2-(1-methylethyl)-1,7-dioxaspiro[5.5]undecan-8-yl}-2-[1-(2-trimethylsilylethoxycarbonyl)-2,3-dihydroxy-4-methoxy-5-methyl-cyclohexan-2-yl]-6,8-dimethyldeca-2,4,8-trienoate

: 135415-62-2,145369-50-2
6β-Hydroxy-3,4-dihydromilbemycin E

Guidance literature:: Multi-step reaction with 4 steps

1: 98 percent / silica gel / CHCl₃ / 16 h

2: 78 percent / tetrabutylammonium fluoride / tetrahydrofuran / 10 h / 20 °C

3: 23 percent / DMAP; dicyclohexylcarbodiimide / CH₂Cl₂ / 16 h / 0 °C

4: 74 percent / DIBAL-H / toluene / 1 h / -78 °C

With dmap; tetrabutyl ammonium fluoride; silica gel; diisobutylaluminium hydride; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; chloroform; toluene;
DOI:10.1039/b508670a