(2R,3R,4R)-2-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-7-en-1-ol

Base Information

Chemical Name:(2R,3R,4R)-2-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-7-en-1-ol
CAS No.:1392307-50-4
Molecular Formula:C₂₄H₄₂O₃Si
Molecular Weight:406.681
Hs Code.:

Synonyms:(2R,3R,4R)-2-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-7-en-1-ol

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Chemical Property of (2R,3R,4R)-2-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-7-en-1-ol

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Technology Process of (2R,3R,4R)-2-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-7-en-1-ol

There total 4 articles about (2R,3R,4R)-2-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-7-en-1-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: 86.0%

: (S)-4-benzyl-3-((2S,3R,4R)-2-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-7-enoyl)oxazolidin-2-one

: 1392307-50-4
(2R,3R,4R)-2-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-7-en-1-ol

Guidance literature:: With sodium tetrahydroborate; In tetrahydrofuran; water; at 0 - 20 ℃;
DOI:10.1002/anie.201108223

Reference yield:

: (S)-4-benzyl-3-((2S,3R,4R)-2-(benzyloxy)-3-hydroxy-4,8-dimethylnon-7-enoyl)oxazolidin-2-one

: 1392307-50-4
(2R,3R,4R)-2-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-7-en-1-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 2,4,6-trimethyl-pyridine / dichloromethane / 0 - 20 °C / Inert atmosphere

2: sodium tetrahydroborate / tetrahydrofuran; water / 0 - 20 °C

With 2,4,6-trimethyl-pyridine; sodium tetrahydroborate; In tetrahydrofuran; dichloromethane; water;
DOI:10.1002/anie.201108223

Reference yield:

: 160488-95-9
(2S,3R)-3,7-dimethyl-6-octene-1,2-diol

: 1392307-50-4
(2R,3R,4R)-2-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-7-en-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium periodate / methanol; water / 0.5 h / 20 °C

2.1: di-n-butylboryl trifluoromethanesulfonate; triethylamine / dichloromethane / 1.25 h / -78 - 0 °C / Inert atmosphere

2.2: 5.5 h / -78 - 0 °C / Inert atmosphere

2.3: -25 - 0 °C / aq. phosphate buffer

3.1: 2,4,6-trimethyl-pyridine / dichloromethane / 0 - 20 °C / Inert atmosphere

4.1: sodium tetrahydroborate / tetrahydrofuran; water / 0 - 20 °C

With 2,4,6-trimethyl-pyridine; sodium tetrahydroborate; sodium periodate; di-n-butylboryl trifluoromethanesulfonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; 2.2: Aldol condensation;
DOI:10.1002/anie.201108223