(2S,3R)-3-Benzyloxy-3-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-2-methyl-propan-1-ol

Base Information

Chemical Name:(2S,3R)-3-Benzyloxy-3-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-2-methyl-propan-1-ol
CAS No.:349552-52-9
Molecular Formula:C₂₂H₃₈O₄Si
Molecular Weight:394.627
Hs Code.:

Synonyms:(2S,3R)-3-Benzyloxy-3-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-2-methyl-propan-1-ol

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Chemical Property of (2S,3R)-3-Benzyloxy-3-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-2-methyl-propan-1-ol

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Technology Process of (2S,3R)-3-Benzyloxy-3-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-2-methyl-propan-1-ol

There total 6 articles about (2S,3R)-3-Benzyloxy-3-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-2-methyl-propan-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: 93.0%

: 349552-51-8
((2R,3S)-2-{(1R,2S)-1-Benzyloxy-3-[(4-methoxy-phenyl)-diphenyl-methoxy]-2-methyl-propyl}-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

: 349552-52-9
(2S,3R)-3-Benzyloxy-3-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-2-methyl-propan-1-ol

Guidance literature:: With pyridinium p-toluenesulfonate; In methanol; dichloromethane; at 23 ℃; for 5h;
DOI:10.1055/s-2001-13387

Reference yield:

: 138750-71-7,125877-82-9
(2'R,3'S)-<3'-(tert-butyldimethylsilyloxy)tetrahydropyran-2'-yl>methanol

: 349552-52-9
(2S,3R)-3-Benzyloxy-3-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-2-methyl-propan-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.55 h / -78 - -18 °C

2.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 2.08 h / -78 - 0 °C

2.2: CH₂Cl₂ / 2.33 h / -78 - -20 °C

3.1: 100 percent / NaBH₄ / tetrahydrofuran; H₂O / 2.8 h / 25 °C

4.1: 100 percent / DMAP; pyridine / CH₂Cl₂ / 2.7 h / 23 °C

5.1: 75 percent / NaH; TBAI / tetrahydrofuran / 20 h / 24 °C

6.1: 93 percent / PPTS / methanol; CH₂Cl₂ / 5 h / 23 °C

With pyridine; dmap; sodium tetrahydroborate; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; 1.1: Swern oxidation / 2.1: Evans aldol reaction;
DOI:10.1055/s-2001-13387

Reference yield:

: 125877-83-0
(2'S,3'S)-3'-(tert-butyldimethylsiloxy)-tetrahydropyran-2'-carbaldehyde

: 349552-52-9
(2S,3R)-3-Benzyloxy-3-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-2-methyl-propan-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 2.08 h / -78 - 0 °C

1.2: CH₂Cl₂ / 2.33 h / -78 - -20 °C

2.1: 100 percent / NaBH₄ / tetrahydrofuran; H₂O / 2.8 h / 25 °C

3.1: 100 percent / DMAP; pyridine / CH₂Cl₂ / 2.7 h / 23 °C

4.1: 75 percent / NaH; TBAI / tetrahydrofuran / 20 h / 24 °C

5.1: 93 percent / PPTS / methanol; CH₂Cl₂ / 5 h / 23 °C

With pyridine; dmap; sodium tetrahydroborate; di-n-butylboryl trifluoromethanesulfonate; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; 1.1: Evans aldol reaction;
DOI:10.1055/s-2001-13387