(2R,3S,5R,8S,9S,10S)-3-(tert-Butyl-dimethyl-silanyloxy)-9-methoxymethoxy-2-[(2R,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-8,10-dimethyl-11-triethylsilanyloxy-undec-6-yn-5-ol

Base Information

Chemical Name:(2R,3S,5R,8S,9S,10S)-3-(tert-Butyl-dimethyl-silanyloxy)-9-methoxymethoxy-2-[(2R,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-8,10-dimethyl-11-triethylsilanyloxy-undec-6-yn-5-ol
CAS No.:216668-84-7
Molecular Formula:C₃₉H₇₀O₈Si₂
Molecular Weight:723.151
Hs Code.:

(2R,3S,5R,8S,9S,10S)-3-(tert-Butyl-dimethyl-silanyloxy)-9-methoxymethoxy-2-[(2R,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-8,10-dimethyl-11-triethylsilanyloxy-undec-6-yn-5-ol

Synonyms:(2R,3S,5R,8S,9S,10S)-3-(tert-Butyl-dimethyl-silanyloxy)-9-methoxymethoxy-2-[(2R,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-8,10-dimethyl-11-triethylsilanyloxy-undec-6-yn-5-ol

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Chemical Property of (2R,3S,5R,8S,9S,10S)-3-(tert-Butyl-dimethyl-silanyloxy)-9-methoxymethoxy-2-[(2R,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-8,10-dimethyl-11-triethylsilanyloxy-undec-6-yn-5-ol

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Technology Process of (2R,3S,5R,8S,9S,10S)-3-(tert-Butyl-dimethyl-silanyloxy)-9-methoxymethoxy-2-[(2R,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-8,10-dimethyl-11-triethylsilanyloxy-undec-6-yn-5-ol

There total 3 articles about (2R,3S,5R,8S,9S,10S)-3-(tert-Butyl-dimethyl-silanyloxy)-9-methoxymethoxy-2-[(2R,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-8,10-dimethyl-11-triethylsilanyloxy-undec-6-yn-5-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:

: 144681-76-5
(2S)-2-methyl-3-(triethylsilyl)oxypropanal

: 216668-84-7
(2R,3S,5R,8S,9S,10S)-3-(tert-Butyl-dimethyl-silanyloxy)-9-methoxymethoxy-2-[(2R,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-8,10-dimethyl-11-triethylsilanyloxy-undec-6-yn-5-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 62 percent / tetrakis-triphenylphosphine pylladium⁽⁰⁾, diethyl zinc / tetrahydrofuran / 1) 0 deg C, 18 h; 2) 0 deg C --> rt, 3 h; 3) rt, 2 h

2: 94 percent / N,N-diisopropylethylamine, tetrabutylammonium iodide / CH₂Cl₂ / 18 h / Ambient temperature

3: 1.) BuLi, 4 Angstroem molecular sieves, 2.) LiBr / 1) THF, hexane, -50 to -40 deg C, 1 h; 2) THF, hexane, -40 deg C, 15 min; 3) THF, hexane, -50 to -40 deg C, 1 h, -40 deg C, 1.5 h

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; 4 A molecular sieve; diethylzinc; tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; lithium bromide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo9811423

Reference yield:

: 216668-18-7
(2S,3S,4S)-2,4-Dimethyl-1-triethylsilanyloxy-hex-5-yn-3-ol

: 216668-84-7
(2R,3S,5R,8S,9S,10S)-3-(tert-Butyl-dimethyl-silanyloxy)-9-methoxymethoxy-2-[(2R,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-8,10-dimethyl-11-triethylsilanyloxy-undec-6-yn-5-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 94 percent / N,N-diisopropylethylamine, tetrabutylammonium iodide / CH₂Cl₂ / 18 h / Ambient temperature

2: 1.) BuLi, 4 Angstroem molecular sieves, 2.) LiBr / 1) THF, hexane, -50 to -40 deg C, 1 h; 2) THF, hexane, -40 deg C, 15 min; 3) THF, hexane, -50 to -40 deg C, 1 h, -40 deg C, 1.5 h

With n-butyllithium; 4 A molecular sieve; tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; lithium bromide; In dichloromethane;
DOI:10.1021/jo9811423

Reference yield:

: 216668-62-1
(3S,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-[(2R,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-pentanal

: 216668-26-7
Triethyl-((2S,3S,4S)-3-methoxymethoxy-2,4-dimethyl-hex-5-ynyloxy)-silane

: 216668-76-7
(2R,3S,5S,8S,9S,10S)-3-(tert-Butyl-dimethyl-silanyloxy)-9-methoxymethoxy-2-[(2R,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-8,10-dimethyl-11-triethylsilanyloxy-undec-6-yn-5-ol

: 216668-84-7
(2R,3S,5R,8S,9S,10S)-3-(tert-Butyl-dimethyl-silanyloxy)-9-methoxymethoxy-2-[(2R,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-8,10-dimethyl-11-triethylsilanyloxy-undec-6-yn-5-ol

Guidance literature:: With n-butyllithium; 4 A molecular sieve; lithium bromide; Yield given. Multistep reaction. Yields of byproduct given; 1) THF, hexane, -50 to -40 deg C, 1 h; 2) THF, hexane, -40 deg C, 15 min; 3) THF, hexane, -50 to -40 deg C, 1 h, -40 deg C, 1.5 h;
DOI:10.1021/jo9811423