(2R,3S)-1-tert-butyldiphenylsilyloxy-cis-2,3-epoxy-5-undecyne

Base Information

• Chemical Name: (2R,3S)-1-tert-butyldiphenylsilyloxy-cis-2,3-epoxy-5-undecyne
• CAS No.: 625847-70-3
• Molecular Formula: C₂₇H₃₆O₂Si
• Molecular Weight: 420.667
• Mol file: 625847-70-3.mol

Synonyms:(2R,3S)-1-tert-butyldiphenylsilyloxy-cis-2,3-epoxy-5-undecyne

Chemical Property of (2R,3S)-1-tert-butyldiphenylsilyloxy-cis-2,3-epoxy-5-undecyne

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-1-tert-butyldiphenylsilyloxy-cis-2,3-epoxy-5-undecyne

There total 2 articles about (2R,3S)-1-tert-butyldiphenylsilyloxy-cis-2,3-epoxy-5-undecyne 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:

1-Heptyne (628-71-7) + Trifluoro-methanesulfonic acid (2S,3R)-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranylmethyl ester → (2R,3S)-1-tert-butyldiphenylsilyloxy-cis-2,3-epoxy-5-undecyne (625847-70-3)

Guidance literature:

1-Heptyne; With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at 0 ℃; for 1h;

Trifluoro-methanesulfonic acid (2S,3R)-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranylmethyl ester; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at -78 ℃; for 1.5h;

DOI:10.1271/bbb.67.1559

Reference yield:

((2S,3R)-3-(((tert-butyldiphenylsilyl)oxy)methyl)oxiran-2-yl)methanol (117901-01-6) → (2R,3S)-1-tert-butyldiphenylsilyloxy-cis-2,3-epoxy-5-undecyne (625847-70-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: tetrahydrofuran; hexane / 0.5 h / -78 °C

2.1: n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 1 h / 0 °C

2.2: 4.40 g / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 1.5 h / -78 °C

With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane;

DOI:10.1271/bbb.67.1559

Reference yield: 100.0%

(2R,3S)-1-tert-butyldiphenylsilyloxy-cis-2,3-epoxy-5-undecyne (625847-70-3) → (2R,3S,5Z)-1-tert-butyldiphenylsilyloxy-cis-2,3-epoxy-5-undecene (625847-71-4)

Guidance literature:

With hydrogen; Lindlar's catalyst; lead⁽²⁺⁾ cation; In cyclohexane; at 20 ℃; for 2h;

DOI:10.1271/bbb.67.1559

upstream raw materials:

1-Heptyne

((2S,3R)-3-(((tert-butyldiphenylsilyl)oxy)methyl)oxiran-2-yl)methanol

Downstream raw materials:

(2R,3S,5Z)-1-tert-butyldiphenylsilyloxy-cis-2,3-epoxy-5-undecene

(5Z)-cis-2R,3S-epoxy-1-O-p-toluenesulfonyl-undecen-1-ol