(2R,3S,10S)-2-benzyloxy-11-tert-butyldimethylsilyloxy-10-methyl-5-undecyn-3-ol

Base Information

Chemical Name:(2R,3S,10S)-2-benzyloxy-11-tert-butyldimethylsilyloxy-10-methyl-5-undecyn-3-ol
CAS No.:443119-46-8
Molecular Formula:C₂₅H₄₂O₃Si
Molecular Weight:418.692
Hs Code.:

Synonyms:(2R,3S,10S)-2-benzyloxy-11-tert-butyldimethylsilyloxy-10-methyl-5-undecyn-3-ol

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Chemical Property of (2R,3S,10S)-2-benzyloxy-11-tert-butyldimethylsilyloxy-10-methyl-5-undecyn-3-ol

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Technology Process of (2R,3S,10S)-2-benzyloxy-11-tert-butyldimethylsilyloxy-10-methyl-5-undecyn-3-ol

There total 9 articles about (2R,3S,10S)-2-benzyloxy-11-tert-butyldimethylsilyloxy-10-methyl-5-undecyn-3-ol 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: 75.0%

: 327186-71-0
(1R)-1-[(2S)-oxiran-2-yl]-1-(benzyloxy)ethane

: 443119-43-5
(6S)-7-tert-butyldimethylsilyloxy-6-methyl-1-heptyne

: 443119-46-8
(2R,3S,10S)-2-benzyloxy-11-tert-butyldimethylsilyloxy-10-methyl-5-undecyn-3-ol

Guidance literature:: With n-butyllithium; boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;
DOI:10.1016/S0957-4166(02)00095-2

Reference yield:

: 97826-89-6
(2R)-3-(tert-butyldimethylsilyloxy)-2-methylpropanal

: 443119-46-8
(2R,3S,10S)-2-benzyloxy-11-tert-butyldimethylsilyloxy-10-methyl-5-undecyn-3-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 82 percent / benzene / 12 h / 20 °C

2: 82 percent / Mg / methanol / 4 h / 20 °C

3: 92 percent / NaBH₄; LiCl / ethanol; tetrahydrofuran / 12 h / 20 °C

4: 85 percent / Et₃N / CH₂Cl₂ / 10 h / 20 °C

5: 73 percent / Li; liq. NH₃ / dimethylsulfoxide / 2 h / 0 °C

6: 75 percent / n-BuLi; BF₃*Et₂O / tetrahydrofuran; hexane / 0.5 h / -78 °C

With sodium tetrahydroborate; n-butyllithium; boron trifluoride diethyl etherate; ammonia; lithium; magnesium; triethylamine; lithium chloride; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; dimethyl sulfoxide; benzene;
DOI:10.1016/S0957-4166(02)00095-2

Reference yield:

: 105859-44-7
methyl (R)-2-methyl-3-[(tert-butyldimethylsilyl)oxy]propionate

: 443119-46-8
(2R,3S,10S)-2-benzyloxy-11-tert-butyldimethylsilyloxy-10-methyl-5-undecyn-3-ol

Guidance literature:: Multi-step reaction with 8 steps

1: 78 percent / DIBAL-H / CH₂Cl₂ / 0 - 20 °C

2: 97 percent / chromium trioxide; pyridine / CH₂Cl₂ / 0.25 h / 20 °C

3: 82 percent / benzene / 12 h / 20 °C

4: 82 percent / Mg / methanol / 4 h / 20 °C

5: 92 percent / NaBH₄; LiCl / ethanol; tetrahydrofuran / 12 h / 20 °C

6: 85 percent / Et₃N / CH₂Cl₂ / 10 h / 20 °C

7: 73 percent / Li; liq. NH₃ / dimethylsulfoxide / 2 h / 0 °C

8: 75 percent / n-BuLi; BF₃*Et₂O / tetrahydrofuran; hexane / 0.5 h / -78 °C

With pyridine; chromium(VI) oxide; sodium tetrahydroborate; n-butyllithium; boron trifluoride diethyl etherate; ammonia; lithium; diisobutylaluminium hydride; magnesium; triethylamine; lithium chloride; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; dimethyl sulfoxide; benzene;
DOI:10.1016/S0957-4166(02)00095-2