(2R,3R,4E,6S,7S,8R,9S,10S)-9-(benzyloxy)-7-[(4-methoxybenzyl)oxy]-11-(methoxymethoxy)-2,6,8,10-tetramethyl-1-[(1,1,1-triisopropylsilyl)oxy]-4-undecen-3-ol

Base Information

Chemical Name:(2R,3R,4E,6S,7S,8R,9S,10S)-9-(benzyloxy)-7-[(4-methoxybenzyl)oxy]-11-(methoxymethoxy)-2,6,8,10-tetramethyl-1-[(1,1,1-triisopropylsilyl)oxy]-4-undecen-3-ol
CAS No.:1320344-50-0
Molecular Formula:C₄₁H₆₈O₇Si
Molecular Weight:701.072
Hs Code.:

Synonyms:(2R,3R,4E,6S,7S,8R,9S,10S)-9-(benzyloxy)-7-[(4-methoxybenzyl)oxy]-11-(methoxymethoxy)-2,6,8,10-tetramethyl-1-[(1,1,1-triisopropylsilyl)oxy]-4-undecen-3-ol

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Chemical Property of (2R,3R,4E,6S,7S,8R,9S,10S)-9-(benzyloxy)-7-[(4-methoxybenzyl)oxy]-11-(methoxymethoxy)-2,6,8,10-tetramethyl-1-[(1,1,1-triisopropylsilyl)oxy]-4-undecen-3-ol

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Technology Process of (2R,3R,4E,6S,7S,8R,9S,10S)-9-(benzyloxy)-7-[(4-methoxybenzyl)oxy]-11-(methoxymethoxy)-2,6,8,10-tetramethyl-1-[(1,1,1-triisopropylsilyl)oxy]-4-undecen-3-ol

There total 9 articles about (2R,3R,4E,6S,7S,8R,9S,10S)-9-(benzyloxy)-7-[(4-methoxybenzyl)oxy]-11-(methoxymethoxy)-2,6,8,10-tetramethyl-1-[(1,1,1-triisopropylsilyl)oxy]-4-undecen-3-ol 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: 66.0%

: 1320344-49-7
(2R,4E,6S,7S,8R,9S,10S)-9-(benzyloxy)-7-[(4-methoxybenzyl)oxy]-11-(methoxymethoxy)-2,6,8,10-tetramethyl-1-[(1,1,1-triisopropylsilyl)oxy]-4-undecen-3-one

: 1320344-50-0
(2R,3R,4E,6S,7S,8R,9S,10S)-9-(benzyloxy)-7-[(4-methoxybenzyl)oxy]-11-(methoxymethoxy)-2,6,8,10-tetramethyl-1-[(1,1,1-triisopropylsilyl)oxy]-4-undecen-3-ol

Guidance literature:: With borane-dimethyl sulfide complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In toluene; at -20 ℃; for 1h; optical yield given as %de; stereoselective reaction; Inert atmosphere;
DOI:10.1055/s-0030-1259967

Reference yield:

: 1320344-48-6
(2S,3S,4R,5S,6S)-5-(benzyloxy)-3-[(4-methoxybenzyl)oxy]-7-(methoxymethoxy)-2,4,6-trimethylheptan-1-ol

: 1320344-50-0
(2R,3R,4E,6S,7S,8R,9S,10S)-9-(benzyloxy)-7-[(4-methoxybenzyl)oxy]-11-(methoxymethoxy)-2,6,8,10-tetramethyl-1-[(1,1,1-triisopropylsilyl)oxy]-4-undecen-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 0 - 20 °C / Inert atmosphere

2.1: barium hydroxide octahydrate / tetrahydrofuran / 0.5 h / Inert atmosphere

2.2: Inert atmosphere

3.1: borane-dimethyl sulfide complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / toluene / 1 h / -20 °C / Inert atmosphere

With borane-dimethyl sulfide complex; barium hydroxide octahydrate; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene; 2.1: Horner-Wadsworth-Emmons olefination;
DOI:10.1055/s-0030-1259967

Reference yield:

: 1204595-67-4
(2S,3S,4S)-3-(benzyloxy)-4-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-2-methylpentan-1-ol

: 1320344-50-0
(2R,3R,4E,6S,7S,8R,9S,10S)-9-(benzyloxy)-7-[(4-methoxybenzyl)oxy]-11-(methoxymethoxy)-2,6,8,10-tetramethyl-1-[(1,1,1-triisopropylsilyl)oxy]-4-undecen-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / dichloromethane / 1 h / -20 - 0 °C / Inert atmosphere

3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 0 - 20 °C / Inert atmosphere

4.1: barium hydroxide octahydrate / tetrahydrofuran / 0.5 h / Inert atmosphere

4.2: Inert atmosphere

5.1: borane-dimethyl sulfide complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / toluene / 1 h / -20 °C / Inert atmosphere

With borane-dimethyl sulfide complex; barium hydroxide octahydrate; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene; 4.1: Horner-Wadsworth-Emmons olefination;
DOI:10.1055/s-0030-1259967