(3S,15R)-15-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-17-iodoandrosta-5,16-diene

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Chemical Name:(3S,15R)-15-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-17-iodoandrosta-5,16-diene
CAS No.:426822-95-9
Molecular Formula:C₃₂H₄₇IO₂Si
Molecular Weight:618.714
Hs Code.:

Synonyms:(3S,15R)-15-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-17-iodoandrosta-5,16-diene

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Chemical Property of (3S,15R)-15-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-17-iodoandrosta-5,16-diene

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Technology Process of (3S,15R)-15-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-17-iodoandrosta-5,16-diene

There total 4 articles about (3S,15R)-15-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-17-iodoandrosta-5,16-diene 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: 98.0%

: 100-39-0
benzyl bromide

: 426823-02-1
(3S,15R)-3-[(tert-butyldimethylsilyl)oxy]-15-hydroxy-17-iodoandrosta-5,16-diene

: 426822-95-9
(3S,15R)-15-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-17-iodoandrosta-5,16-diene

Guidance literature:: (3S,15R)-3-[(tert-butyldimethylsilyl)oxy]-15-hydroxy-17-iodoandrosta-5,16-diene; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 1h;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; at 20 ℃; for 17h;
DOI:10.1135/cccc20011797

Reference yield:

: 78424-46-1
3β-t-butyldimethylsiloxy-15β-16β-epoxy-5-androsten-17-one

: 426822-95-9
(3S,15R)-15-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-17-iodoandrosta-5,16-diene

Guidance literature:: Multi-step reaction with 4 steps

1.1: 96 percent / NaBH₄; PhSeSePh; AcOH / ethanol / 2 h

2.1: 98 percent / aq. NH₂NH₂*H₂O; Et₃N / ethanol / 12 h

3.1: 64 percent / 1,1,3,3-tetramethylguanidine; iodine / tetrahydrofuran / 0.5 h / 0 °C

4.1: NaH / tetrahydrofuran / 1 h / 20 °C

4.2: 98 percent / Bu₄NI / tetrahydrofuran / 17 h / 20 °C

With sodium tetrahydroborate; diphenyl diselenide; iodine; sodium hydride; hydrazine hydrate; acetic acid; triethylamine; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; ethanol;
DOI:10.1135/cccc20011797

Reference yield:

: 426823-01-0
(3S,8R,9S,10R,13S,14S,15R)-3-(tert-Butyl-dimethyl-silanyloxy)-17-hydrazono-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-15-ol

: 426822-95-9
(3S,15R)-15-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-17-iodoandrosta-5,16-diene

Guidance literature:: Multi-step reaction with 2 steps

1.1: 64 percent / 1,1,3,3-tetramethylguanidine; iodine / tetrahydrofuran / 0.5 h / 0 °C

2.1: NaH / tetrahydrofuran / 1 h / 20 °C

2.2: 98 percent / Bu₄NI / tetrahydrofuran / 17 h / 20 °C

With iodine; sodium hydride; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran;
DOI:10.1135/cccc20011797