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

Base Information

• Chemical Name: (2S,6S)-2-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-6-(prop-1-yn-1-yl)dihydro-2H-pyran-4(3H)-one
• CAS No.: 1227307-22-3
• Molecular Formula: C₂₆H₃₂O₃Si
• Molecular Weight: 420.624
• Mol file: 1227307-22-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about (2S,6S)-2-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-6-(prop-1-yn-1-yl)dihydro-2H-pyran-4(3H)-one 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:

C26H34O3Si (1437312-99-6) → (2S,6S)-2-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-6-(prop-1-yn-1-yl)dihydro-2H-pyran-4(3H)-one (1227307-22-3)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; for 3h; 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,6S)-2-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-6-(prop-1-yn-1-yl)dihydro-2H-pyran-4(3H)-one (1227307-22-3) + C26H32O3Si (1437312-94-1)

Guidance literature:

1-(((S)-1-((tert-butyldiphenylsilyl)oxy)hex-5-en-3-yl)oxy)but-2-yn-1-yl acetate; In dichloromethane; at 0 ℃; for 0.5h;

With potassium carbonate; In methanol; at 20 ℃; for 0.75h;

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 2.5h; Overall yield = 90 %;

DOI:10.1002/chem.201202553

Reference yield:

1-(((S)-1-((tert-butyldiphenylsilyl)oxy)hex-5-en-3-yl)oxy)but-2-yn-1-yl acetate → (2S,6S)-2-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-6-(prop-1-yn-1-yl)dihydro-2H-pyran-4(3H)-one (1227307-22-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dichloromethane / 0.5 h / 0 °C

1.2: 0.75 h / 20 °C

2.1: Dess-Martin periodane / dichloromethane / 3 h

With Dess-Martin periodane; In dichloromethane;

DOI:10.1002/chem.201202553

upstream raw materials:

C₂₆H₃₄O₃Si

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

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

Downstream raw materials:

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