tert-butyl-(2-((2R,6S)-4-methylene-6-(prop-1-ynyl-)tetrahydro-2H-pyran-2-yl)ethoxy)diphenylsilane

Base Information

Chemical Name:tert-butyl-(2-((2R,6S)-4-methylene-6-(prop-1-ynyl-)tetrahydro-2H-pyran-2-yl)ethoxy)diphenylsilane
CAS No.:1227307-13-2
Molecular Formula:C₂₇H₃₄O₂Si
Molecular Weight:418.651
Hs Code.:

Synonyms:tert-butyl-(2-((2R,6S)-4-methylene-6-(prop-1-ynyl-)tetrahydro-2H-pyran-2-yl)ethoxy)diphenylsilane

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Chemical Property of tert-butyl-(2-((2R,6S)-4-methylene-6-(prop-1-ynyl-)tetrahydro-2H-pyran-2-yl)ethoxy)diphenylsilane

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Technology Process of tert-butyl-(2-((2R,6S)-4-methylene-6-(prop-1-ynyl-)tetrahydro-2H-pyran-2-yl)ethoxy)diphenylsilane

There total 4 articles about tert-butyl-(2-((2R,6S)-4-methylene-6-(prop-1-ynyl-)tetrahydro-2H-pyran-2-yl)ethoxy)diphenylsilane 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: 94.0%

: 1227307-22-3
(2S,6S)-2-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-6-(prop-1-yn-1-yl)dihydro-2H-pyran-4(3H)-one

: 1779-49-3
Methyltriphenylphosphonium bromide

: 1227307-13-2
tert-butyl-(2-((2R,6S)-4-methylene-6-(prop-1-ynyl-)tetrahydro-2H-pyran-2-yl)ethoxy)diphenylsilane

Guidance literature:: Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 0 ℃; Inert atmosphere;

(2S,6S)-2-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-6-(prop-1-yn-1-yl)dihydro-2H-pyran-4(3H)-one; In tetrahydrofuran; hexane; at 0 - 50 ℃; for 1.5h; Inert atmosphere;
DOI:10.1021/ol100665m

Reference yield: 94.0%

: 1227307-21-2
(2S,4R,6S)-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-6-(prop-1-ynyl)tetrahydro-2H-pyran-4-yl acetate

: 1779-49-3
Methyltriphenylphosphonium bromide

: 1227307-13-2
tert-butyl-(2-((2R,6S)-4-methylene-6-(prop-1-ynyl-)tetrahydro-2H-pyran-2-yl)ethoxy)diphenylsilane

Guidance literature:: Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 0.75h;

(2S,4R,6S)-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-6-(prop-1-ynyl)tetrahydro-2H-pyran-4-yl acetate; In tetrahydrofuran; hexane; at 50 ℃; for 1.5h;
DOI:10.1002/chem.201202553

Reference yield:

: 1227307-12-1
tert-butyl-(2-((2S,4S,6S)-4-iodo-6-(prop-1-ynyl)tetrahydro-2H-pyran-2-yl)ethoxy)diphenylsilane

: 1227307-13-2
tert-butyl-(2-((2R,6S)-4-methylene-6-(prop-1-ynyl-)tetrahydro-2H-pyran-2-yl)ethoxy)diphenylsilane

Guidance literature:: Multi-step reaction with 2 steps

1.1: 18-crown-6 ether / toluene / 96 h / 20 - 60 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 - 0 °C

2.2: 1.5 h / 50 °C

With n-butyllithium; 18-crown-6 ether; In tetrahydrofuran; hexane; toluene;
DOI:10.1002/chem.201202553