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

Base Information

• Chemical Name: (2S,4R,6S)-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-6-(prop-1-ynyl)tetrahydro-2H-pyran-4-yl acetate
• CAS No.: 1227307-21-2
• Molecular Formula: C₂₈H₃₆O₄Si
• Molecular Weight: 464.677

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

Chemical Property of (2S,4R,6S)-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-6-(prop-1-ynyl)tetrahydro-2H-pyran-4-yl acetate

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of (2S,4R,6S)-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-6-(prop-1-ynyl)tetrahydro-2H-pyran-4-yl acetate

There total 2 articles about (2S,4R,6S)-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-6-(prop-1-ynyl)tetrahydro-2H-pyran-4-yl acetate 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: 72.0%

tert-butyl-(2-((2S,4S,6S)-4-iodo-6-(prop-1-ynyl)tetrahydro-2H-pyran-2-yl)ethoxy)diphenylsilane (1227307-12-1) + cesium acetate (3396-11-0) → (2S,4R,6S)-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-6-(prop-1-ynyl)tetrahydro-2H-pyran-4-yl acetate (1227307-21-2)

Guidance literature:

With 18-crown-6 ether; In toluene; at 20 - 60 ℃; for 96h; Inert atmosphere;

DOI:10.1021/ol100665m

Reference yield:

1-(((S)-1-((tert-butyldiphenylsilyl)oxy)hex-5-en-3-yl)oxy)but-2-yn-1-yl acetate → (2S,4R,6S)-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-6-(prop-1-ynyl)tetrahydro-2H-pyran-4-yl acetate (1227307-21-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 2,6-dimethylpyridine; trimethylsilyl iodide / dichloromethane / 0.92 h / -19 - 20 °C

2: 18-crown-6 ether / toluene / 96 h / 20 - 60 °C

With 2,6-dimethylpyridine; 18-crown-6 ether; trimethylsilyl iodide; In dichloromethane; toluene;

DOI:10.1002/chem.201202553

Reference yield: 94.0%

(2S,4R,6S)-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-6-(prop-1-ynyl)tetrahydro-2H-pyran-4-yl acetate (1227307-21-2) + Methyltriphenylphosphonium bromide (1779-49-3) → tert-butyl-(2-((2R,6S)-4-methylene-6-(prop-1-ynyl-)tetrahydro-2H-pyran-2-yl)ethoxy)diphenylsilane (1227307-13-2)

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

upstream raw materials:

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

cesium acetate

Downstream raw materials:

C₂₆H₃₄O₃Si

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

tert-butyl-(2-((2R,6S)-6-((E)-2-iodoprop-1-enyl)-4-methylenetetrahydro-2H-pyran-2-yl)ethoxy)diphenylsilane

C₃₉H₆₂O₂SiSn

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