(2S,4S)-2-(3-tert-butyldiphenylsilyloxy-prop-1-ynyl)-3,4-dihydro-4-hydroxy-2H-pyran

Base Information

• Chemical Name: (2S,4S)-2-(3-tert-butyldiphenylsilyloxy-prop-1-ynyl)-3,4-dihydro-4-hydroxy-2H-pyran
• CAS No.: 1141494-06-5
• Molecular Formula: C₂₄H₂₈O₃Si
• Molecular Weight: 392.57
• Mol file: 1141494-06-5.mol

Synonyms:(2S,4S)-2-(3-tert-butyldiphenylsilyloxy-prop-1-ynyl)-3,4-dihydro-4-hydroxy-2H-pyran

Chemical Property of (2S,4S)-2-(3-tert-butyldiphenylsilyloxy-prop-1-ynyl)-3,4-dihydro-4-hydroxy-2H-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S)-2-(3-tert-butyldiphenylsilyloxy-prop-1-ynyl)-3,4-dihydro-4-hydroxy-2H-pyran

There total 3 articles about (2S,4S)-2-(3-tert-butyldiphenylsilyloxy-prop-1-ynyl)-3,4-dihydro-4-hydroxy-2H-pyran 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: 83.0%

(S)-2-[3-(tert-butyldiphenylsilyloxy)-prop-1-ynyl]-2,3-dihydropyran-4-one (1141494-05-4) → (2S,4S)-2-(3-tert-butyldiphenylsilyloxy-prop-1-ynyl)-3,4-dihydro-4-hydroxy-2H-pyran (1141494-06-5) + (2S,4R)-2-(3-tert-butyldiphenylsilyloxy-prop-1-ynyl)-3,4-dihydro-4-hydroxy-2H-pyran (1141494-22-5)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride heptahydrate; In methanol; ethanol; at -115 - -90 ℃; for 0.5h; optical yield given as %ee;

DOI:10.1002/anie.200805395

Reference yield: 43.0%

(cis)-4-acetoxy-2-(3-tert-butyldiphenylsilyloxy-prop-1-ynyl)-3,4-dihydro-2H-pyran → (2S,4S)-2-(3-tert-butyldiphenylsilyloxy-prop-1-ynyl)-3,4-dihydro-4-hydroxy-2H-pyran (1141494-06-5)

Guidance literature:

With PS Amano lipase (Burkholderia cepacia from Amano Enzyme, Inc_.); In acetone; at 20 ℃; for 9h; pH=7; optical yield given as %ee; aq. buffer; Resolution of racemate; Enzymatic reaction;

DOI:10.1002/anie.200805395

Reference yield:

2-[3-(tert-butyldiphenylsilyloxy)-prop-1-ynyl]-2,3-dihydropyran-4-one (1141494-21-4) → (2S,4S)-2-(3-tert-butyldiphenylsilyloxy-prop-1-ynyl)-3,4-dihydro-4-hydroxy-2H-pyran (1141494-06-5) + (2R,4R)-2-(3-tert-butyldiphenylsilyloxy-prop-1-ynyl)-3,4-dihydro-4-hydroxy-2H-pyran

Guidance literature:

2-[3-(tert-butyldiphenylsilyloxy)-prop-1-ynyl]-2,3-dihydropyran-4-one; With sodium tetrahydroborate; cerium(III) chloride heptahydrate; In methanol; ethanol; at -78 ℃; for 0.5h; Inert atmosphere;

With water; In methanol; ethanol; Inert atmosphere;

DOI:10.1039/b919535a

upstream raw materials:

(S)-2-[3-(tert-butyldiphenylsilyloxy)-prop-1-ynyl]-2,3-dihydropyran-4-one

2-[3-(tert-butyldiphenylsilyloxy)-prop-1-ynyl]-2,3-dihydropyran-4-one

Downstream raw materials:

(2S,4S)-4-(tert-butyldimethylsilyloxy)-2-(3-tert-butyldiphenylsilyloxy-prop-1-ynyl)-3,4-dihydro-2H-pyran