(-)-(4R,6S,7S)-7-((benzyloxy)methoxy)-6-((tert-butyldimethylsilyl)-oxy)-8-methylnon-1-en-4-ol

Base Information

Chemical Name:(-)-(4R,6S,7S)-7-((benzyloxy)methoxy)-6-((tert-butyldimethylsilyl)-oxy)-8-methylnon-1-en-4-ol
CAS No.:1318231-04-7
Molecular Formula:C₂₄H₄₂O₄Si
Molecular Weight:422.681
Hs Code.:

Synonyms:(-)-(4R,6S,7S)-7-((benzyloxy)methoxy)-6-((tert-butyldimethylsilyl)-oxy)-8-methylnon-1-en-4-ol

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Chemical Property of (-)-(4R,6S,7S)-7-((benzyloxy)methoxy)-6-((tert-butyldimethylsilyl)-oxy)-8-methylnon-1-en-4-ol

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Technology Process of (-)-(4R,6S,7S)-7-((benzyloxy)methoxy)-6-((tert-butyldimethylsilyl)-oxy)-8-methylnon-1-en-4-ol

There total 5 articles about (-)-(4R,6S,7S)-7-((benzyloxy)methoxy)-6-((tert-butyldimethylsilyl)-oxy)-8-methylnon-1-en-4-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%

: 1318231-03-6
(-)-(5S,6S)-5-isopropyl-8,8,9,9-tetramethyl-1-phenyl-6-vinyl-2,4,7-trioxa-8-siladecane

: 1318231-04-7
(-)-(4R,6S,7S)-7-((benzyloxy)methoxy)-6-((tert-butyldimethylsilyl)-oxy)-8-methylnon-1-en-4-ol

Guidance literature:: (-)-(5S,6S)-5-isopropyl-8,8,9,9-tetramethyl-1-phenyl-6-vinyl-2,4,7-trioxa-8-siladecane; With 2-methyl-but-2-ene; BH₃-Me₂S; In tetrahydrofuran; at 0 - 45 ℃; Inert atmosphere;

With water; dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; at 0 - 20 ℃; for 3h; Inert atmosphere;
DOI:10.1021/ja206013j

Reference yield:

: 1318230-47-5
(-)-(R)-2-((2-methylhex-5-en-3-yl)oxy)acetic acid

: 1318231-04-7
(-)-(4R,6S,7S)-7-((benzyloxy)methoxy)-6-((tert-butyldimethylsilyl)-oxy)-8-methylnon-1-en-4-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: lithium hydroxide / tetrahydrofuran; water / 0.5 h / 0 °C / pH 4 / Inert atmosphere

1.2: 0 °C / Inert atmosphere

2.1: samarium diiodide; ethylene glycol / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide / 12 h / 20 °C / Inert atmosphere

3.1: tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

4.1: BH₃-Me₂S; 2-methyl-but-2-ene / tetrahydrofuran / 0 - 45 °C / Inert atmosphere

4.2: 3 h / 0 - 20 °C / Inert atmosphere

With samarium diiodide; 2-methyl-but-2-ene; BH₃-Me₂S; tetra-(n-butyl)ammonium iodide; ethylene glycol; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water;
DOI:10.1021/ja206013j

Reference yield:

: 88691-75-2
(3R)-2-methyl-hex-5-en-3-ol

: 1318231-04-7
(-)-(4R,6S,7S)-7-((benzyloxy)methoxy)-6-((tert-butyldimethylsilyl)-oxy)-8-methylnon-1-en-4-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydride / tetrahydrofuran / 0 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

2.1: lithium hydroxide / tetrahydrofuran; water / 0.5 h / 0 °C / pH 4 / Inert atmosphere

2.2: 0 °C / Inert atmosphere

3.1: samarium diiodide; ethylene glycol / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide / 12 h / 20 °C / Inert atmosphere

4.1: tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

5.1: BH₃-Me₂S; 2-methyl-but-2-ene / tetrahydrofuran / 0 - 45 °C / Inert atmosphere

5.2: 3 h / 0 - 20 °C / Inert atmosphere

With samarium diiodide; 2-methyl-but-2-ene; BH₃-Me₂S; tetra-(n-butyl)ammonium iodide; sodium hydride; ethylene glycol; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water;
DOI:10.1021/ja206013j