tert-butyl (2S,3R)-4-(tert-butyldiphenylsilyl)oxy-3-hydroxy-2-(tetrahydropyran-2-yl)oxybutanoate

Base Information

Chemical Name:tert-butyl (2S,3R)-4-(tert-butyldiphenylsilyl)oxy-3-hydroxy-2-(tetrahydropyran-2-yl)oxybutanoate
CAS No.:644981-40-8
Molecular Formula:C₂₉H₄₂O₆Si
Molecular Weight:514.734
Hs Code.:

Synonyms:tert-butyl (2S,3R)-4-(tert-butyldiphenylsilyl)oxy-3-hydroxy-2-(tetrahydropyran-2-yl)oxybutanoate

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Chemical Property of tert-butyl (2S,3R)-4-(tert-butyldiphenylsilyl)oxy-3-hydroxy-2-(tetrahydropyran-2-yl)oxybutanoate

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Technology Process of tert-butyl (2S,3R)-4-(tert-butyldiphenylsilyl)oxy-3-hydroxy-2-(tetrahydropyran-2-yl)oxybutanoate

There total 7 articles about tert-butyl (2S,3R)-4-(tert-butyldiphenylsilyl)oxy-3-hydroxy-2-(tetrahydropyran-2-yl)oxybutanoate 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: 96.0%

: 644981-39-5
tert-butyl (2S,3R)-4-(tert-butyldiphenylsilyl)oxy-3-(4-methoxybenzyl)oxy-2-(tetrahydropyran-2-yl)oxybutanoate

: 644981-40-8
tert-butyl (2S,3R)-4-(tert-butyldiphenylsilyl)oxy-3-hydroxy-2-(tetrahydropyran-2-yl)oxybutanoate

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; for 2h; pH=7;
DOI:10.1002/anie.200352629

Reference yield:

: 117384-46-0
di-tert-butyl D-tartrate

: 644981-40-8
tert-butyl (2S,3R)-4-(tert-butyldiphenylsilyl)oxy-3-hydroxy-2-(tetrahydropyran-2-yl)oxybutanoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: Bu₂SnO / toluene / 2 h / Heating

1.2: 92 percent / cesium fluoride / dimethylformamide / 10 h

2.1: LiBH₄ / tetrahydrofuran / 4 h / 20 °C

2.2: 24.5 g / LiBH₄ / tetrahydrofuran / 4 h / -78 °C

3.1: 97 percent / imidazole / CH₂Cl₂ / 0.5 h / 0 °C

4.1: 95 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 5 h

5.1: 96 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; aq. phosphate buffer / 2 h / pH 7

With 1H-imidazole; lithium borohydride; pyridinium p-toluenesulfonate; di(n-butyl)tin oxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; phosphate buffer; dichloromethane; toluene;
DOI:10.1002/chem.200601212

Reference yield:

: 644981-36-2
di-tert-butyl (2S,3S)-2-hydroxy-3-(4-methoxybenzyl)oxybutanedioate

: 644981-40-8
tert-butyl (2S,3R)-4-(tert-butyldiphenylsilyl)oxy-3-hydroxy-2-(tetrahydropyran-2-yl)oxybutanoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: LiBH₄ / tetrahydrofuran / 4 h / 20 °C

1.2: 24.5 g / LiBH₄ / tetrahydrofuran / 4 h / -78 °C

2.1: 97 percent / imidazole / CH₂Cl₂ / 0.5 h / 0 °C

3.1: 95 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 5 h

4.1: 96 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; aq. phosphate buffer / 2 h / pH 7

With 1H-imidazole; lithium borohydride; pyridinium p-toluenesulfonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; phosphate buffer; dichloromethane;
DOI:10.1002/chem.200601212