1α,3β-bis[(tert-butyldimethylsilyl)oxy]-9α-methyl-25-[(triethylsilyl)oxy]-9,10-secocholest-5(10)-en-6-yn-8β-ol

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Chemical Name:1α,3β-bis[(tert-butyldimethylsilyl)oxy]-9α-methyl-25-[(triethylsilyl)oxy]-9,10-secocholest-5(10)-en-6-yn-8β-ol
CAS No.:1421640-73-4
Molecular Formula:C₄₆H₈₈O₄Si₃
Molecular Weight:789.459
Hs Code.:

Synonyms:1α,3β-bis[(tert-butyldimethylsilyl)oxy]-9α-methyl-25-[(triethylsilyl)oxy]-9,10-secocholest-5(10)-en-6-yn-8β-ol

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Chemical Property of 1α,3β-bis[(tert-butyldimethylsilyl)oxy]-9α-methyl-25-[(triethylsilyl)oxy]-9,10-secocholest-5(10)-en-6-yn-8β-ol

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Technology Process of 1α,3β-bis[(tert-butyldimethylsilyl)oxy]-9α-methyl-25-[(triethylsilyl)oxy]-9,10-secocholest-5(10)-en-6-yn-8β-ol

There total 2 articles about 1α,3β-bis[(tert-butyldimethylsilyl)oxy]-9α-methyl-25-[(triethylsilyl)oxy]-9,10-secocholest-5(10)-en-6-yn-8β-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: 76.0%

: 1421640-67-6
(1R,3aR,5R,7aR)-1-[(R)-1’,5’-dimethyl-5’-[(triethylsilyl)oxy]hexyl]-5,7a-dimethyloctahydroinden-4-one

: 116506-67-3
TB

: 1421640-73-4
1α,3β-bis[(tert-butyldimethylsilyl)oxy]-9α-methyl-25-[(triethylsilyl)oxy]-9,10-secocholest-5(10)-en-6-yn-8β-ol

Guidance literature:: TB; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.0833333h; Inert atmosphere;

With cerium(III) chloride; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

(1R,3aR,5R,7aR)-1-[(R)-1’,5’-dimethyl-5’-[(triethylsilyl)oxy]hexyl]-5,7a-dimethyloctahydroinden-4-one; In tetrahydrofuran; hexane; at -78 - 20 ℃; Inert atmosphere;
DOI:10.1021/jo302513e

Reference yield:

: 144848-24-8
25-[(triethylsilyl)oxy]de-A,B-cholestan-8-one

: 1421640-73-4
1α,3β-bis[(tert-butyldimethylsilyl)oxy]-9α-methyl-25-[(triethylsilyl)oxy]-9,10-secocholest-5(10)-en-6-yn-8β-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: lithium diisopropyl amide; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / tetrahydrofuran; n-heptane; ethylbenzene / 1 h / -78 - -30 °C / Inert atmosphere

1.2: 4 h / -78 - -30 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h / -78 °C / Inert atmosphere

2.2: 0.5 h / -78 °C / Inert atmosphere

2.3: -78 - 20 °C / Inert atmosphere

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; lithium diisopropyl amide; In tetrahydrofuran; hexane; n-heptane; ethylbenzene;
DOI:10.1021/jo302513e