(2S,3R)-1-benzyloxy-2-[(tert-butyldimethylsilyl)oxy]-3-methyl-5-pentanol

Base Information

Chemical Name:(2S,3R)-1-benzyloxy-2-[(tert-butyldimethylsilyl)oxy]-3-methyl-5-pentanol
CAS No.:850699-22-8
Molecular Formula:C₁₉H₃₄O₃Si
Molecular Weight:338.563
Hs Code.:

Synonyms:(2S,3R)-1-benzyloxy-2-[(tert-butyldimethylsilyl)oxy]-3-methyl-5-pentanol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,3R)-1-benzyloxy-2-[(tert-butyldimethylsilyl)oxy]-3-methyl-5-pentanol

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Technology Process of (2S,3R)-1-benzyloxy-2-[(tert-butyldimethylsilyl)oxy]-3-methyl-5-pentanol

There total 3 articles about (2S,3R)-1-benzyloxy-2-[(tert-butyldimethylsilyl)oxy]-3-methyl-5-pentanol 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: 99.0%

: 850699-11-5
(3S,4R)-5-benzyloxy-3-methyl-4-[(tert-butyldimethylsilyl)oxy]-1-pentene

: 850699-22-8
(2S,3R)-1-benzyloxy-2-[(tert-butyldimethylsilyl)oxy]-3-methyl-5-pentanol

Guidance literature:: (3S,4R)-5-benzyloxy-3-methyl-4-[(tert-butyldimethylsilyl)oxy]-1-pentene; With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; at 0 - 20 ℃; for 15h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 0 - 20 ℃; for 19h;
DOI:10.1021/ol050250q

Reference yield:

: 60656-87-3
benzyloxyacetoaldehyde

: 850699-22-8
(2S,3R)-1-benzyloxy-2-[(tert-butyldimethylsilyl)oxy]-3-methyl-5-pentanol

Guidance literature:: Multi-step reaction with 3 steps

1.1: t-BuOK; n-BuLi / tetrahydrofuran; hexane / 0.25 h / -45 °C

1.2: BF₃*Et₂O; (+)-Ipc₂BOMe / tetrahydrofuran; hexane; diethyl ether / -70 - -40 °C

1.3: aq. NaOH; aq. H₂O₂ / tetrahydrofuran; hexane; diethyl ether / 3 h / 20 - 60 °C

2.1: 22.7 g / imidazole; DMAP / dimethylformamide / 20 °C

3.1: 9-BBN / tetrahydrofuran / 15 h / 0 - 20 °C

3.2: 99 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 19 h / 0 - 20 °C

With 1H-imidazole; dmap; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; potassium tert-butylate; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;
DOI:10.1021/ol050250q

Reference yield:

: 635727-09-2
(2R,3S)-1-Benzyloxy-3-methyl-pent-4-en-2-ol

: 850699-22-8
(2S,3R)-1-benzyloxy-2-[(tert-butyldimethylsilyl)oxy]-3-methyl-5-pentanol

Guidance literature:: Multi-step reaction with 2 steps

1.1: 22.7 g / imidazole; DMAP / dimethylformamide / 20 °C

2.1: 9-BBN / tetrahydrofuran / 15 h / 0 - 20 °C

2.2: 99 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 19 h / 0 - 20 °C

With 1H-imidazole; dmap; 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/ol050250q