(2S/R,8R,E)-11-(tert-butyldimethylsilyloxy)-8-hydroxyundec-9-en-6-yn-2-yl benzoate

Base Information

Chemical Name:(2S/R,8R,E)-11-(tert-butyldimethylsilyloxy)-8-hydroxyundec-9-en-6-yn-2-yl benzoate
CAS No.:1361250-57-8
Molecular Formula:C₂₄H₃₆O₄Si
Molecular Weight:416.633
Hs Code.:

Synonyms:(2S/R,8R,E)-11-(tert-butyldimethylsilyloxy)-8-hydroxyundec-9-en-6-yn-2-yl benzoate

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Chemical Property of (2S/R,8R,E)-11-(tert-butyldimethylsilyloxy)-8-hydroxyundec-9-en-6-yn-2-yl benzoate

Chemical Property:

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Technology Process of (2S/R,8R,E)-11-(tert-butyldimethylsilyloxy)-8-hydroxyundec-9-en-6-yn-2-yl benzoate

There total 7 articles about (2S/R,8R,E)-11-(tert-butyldimethylsilyloxy)-8-hydroxyundec-9-en-6-yn-2-yl benzoate 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: 64.0%

: 127382-61-0,119125-30-3
(E)-4-((tert-butyldimethylsilyl)oxy)but-2-enal

: 742078-66-6
(±)-hept-6-yn-2-yl benzoate

: 1361250-57-8
(2S/R,8R,E)-11-(tert-butyldimethylsilyloxy)-8-hydroxyundec-9-en-6-yn-2-yl benzoate

Guidance literature:: With dimethyl zinc(II); Triphenylphosphine oxide; ((2S,2'S)-((2-hydroxy-5-methyl-1,3-phenylene)bis(methylene))bis(pyrrolidine-1,2-diyl))bis(diphenylmethanol); In toluene; at 4 ℃; for 48h; optical yield given as %ee; Inert atmosphere;
DOI:10.1021/ol300200m

Reference yield:

: 91202-69-6,134297-05-5,113123-37-8
(Z)-4-(tert-butyldimethylsilyloxy)but-2-en-1-ol

: 1361250-57-8
(2S/R,8R,E)-11-(tert-butyldimethylsilyloxy)-8-hydroxyundec-9-en-6-yn-2-yl benzoate

Guidance literature:: Multi-step reaction with 2 steps

1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

2: dimethyl zinc(II); Triphenylphosphine oxide; ((2S,2'S)-((2-hydroxy-5-methyl-1,3-phenylene)bis(methylene))bis(pyrrolidine-1,2-diyl))bis(diphenylmethanol) / toluene / 48 h / 4 °C / Inert atmosphere

With dimethyl zinc(II); sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; Triphenylphosphine oxide; ((2S,2'S)-((2-hydroxy-5-methyl-1,3-phenylene)bis(methylene))bis(pyrrolidine-1,2-diyl))bis(diphenylmethanol); In dichloromethane; toluene;
DOI:10.1021/ol300200m

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1361250-57-8
(2S/R,8R,E)-11-(tert-butyldimethylsilyloxy)-8-hydroxyundec-9-en-6-yn-2-yl benzoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.25 h / 0 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

2.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

3.1: dimethyl zinc(II); Triphenylphosphine oxide; ((2S,2'S)-((2-hydroxy-5-methyl-1,3-phenylene)bis(methylene))bis(pyrrolidine-1,2-diyl))bis(diphenylmethanol) / toluene / 48 h / 4 °C / Inert atmosphere

With dimethyl zinc(II); sulfur trioxide pyridine complex; sodium hydride; dimethyl sulfoxide; triethylamine; Triphenylphosphine oxide; ((2S,2'S)-((2-hydroxy-5-methyl-1,3-phenylene)bis(methylene))bis(pyrrolidine-1,2-diyl))bis(diphenylmethanol); In tetrahydrofuran; dichloromethane; toluene; mineral oil;
DOI:10.1021/ol300200m