Benzoic acid (1S,4S,5S,6S)-1-{(2S,3R)-2-(tert-butyl-dimethyl-silanyloxy)-3-[(2R,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-butyl}-5-methoxymethoxy-4,6-dimethyl-7-triethylsilanyloxy-hept-2-ynyl ester

Base Information

Chemical Name:Benzoic acid (1S,4S,5S,6S)-1-{(2S,3R)-2-(tert-butyl-dimethyl-silanyloxy)-3-[(2R,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-butyl}-5-methoxymethoxy-4,6-dimethyl-7-triethylsilanyloxy-hept-2-ynyl ester
CAS No.:216668-90-5
Molecular Formula:C₄₆H₇₄O₉Si₂
Molecular Weight:827.259
Hs Code.:

Benzoic acid (1S,4S,5S,6S)-1-{(2S,3R)-2-(tert-butyl-dimethyl-silanyloxy)-3-[(2R,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-butyl}-5-methoxymethoxy-4,6-dimethyl-7-triethylsilanyloxy-hept-2-ynyl ester

Synonyms:Benzoic acid (1S,4S,5S,6S)-1-{(2S,3R)-2-(tert-butyl-dimethyl-silanyloxy)-3-[(2R,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-butyl}-5-methoxymethoxy-4,6-dimethyl-7-triethylsilanyloxy-hept-2-ynyl ester

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Chemical Property of Benzoic acid (1S,4S,5S,6S)-1-{(2S,3R)-2-(tert-butyl-dimethyl-silanyloxy)-3-[(2R,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-butyl}-5-methoxymethoxy-4,6-dimethyl-7-triethylsilanyloxy-hept-2-ynyl ester

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Technology Process of Benzoic acid (1S,4S,5S,6S)-1-{(2S,3R)-2-(tert-butyl-dimethyl-silanyloxy)-3-[(2R,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-butyl}-5-methoxymethoxy-4,6-dimethyl-7-triethylsilanyloxy-hept-2-ynyl ester

There total 4 articles about Benzoic acid (1S,4S,5S,6S)-1-{(2S,3R)-2-(tert-butyl-dimethyl-silanyloxy)-3-[(2R,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-butyl}-5-methoxymethoxy-4,6-dimethyl-7-triethylsilanyloxy-hept-2-ynyl 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: 82.0%

: 65-85-0,8013-63-6
benzoic acid

: 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

: 216668-90-5
Benzoic acid (1S,4S,5S,6S)-1-{(2S,3R)-2-(tert-butyl-dimethyl-silanyloxy)-3-[(2R,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-butyl}-5-methoxymethoxy-4,6-dimethyl-7-triethylsilanyloxy-hept-2-ynyl ester

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; for 21h; Ambient temperature;
DOI:10.1021/jo9811423

Reference yield:

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

: 216668-90-5
Benzoic acid (1S,4S,5S,6S)-1-{(2S,3R)-2-(tert-butyl-dimethyl-silanyloxy)-3-[(2R,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-butyl}-5-methoxymethoxy-4,6-dimethyl-7-triethylsilanyloxy-hept-2-ynyl ester

Guidance literature:: Multi-step reaction with 4 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

4: 82 percent / Ph₃P, diisopropyl azodicarboxylate / tetrahydrofuran / 21 h / Ambient temperature

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; di-isopropyl azodicarboxylate; 4 A molecular sieve; diethylzinc; tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 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

: 216668-90-5
Benzoic acid (1S,4S,5S,6S)-1-{(2S,3R)-2-(tert-butyl-dimethyl-silanyloxy)-3-[(2R,4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-butyl}-5-methoxymethoxy-4,6-dimethyl-7-triethylsilanyloxy-hept-2-ynyl ester

Guidance literature:: Multi-step reaction with 3 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

3: 82 percent / Ph₃P, diisopropyl azodicarboxylate / tetrahydrofuran / 21 h / Ambient temperature

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