(+)-(R)-2-((2S,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)-propan-2-yl)-5-methyltetrahydro-2H-pyran-2-yl)propan-1-ol

Base Information

Chemical Name:(+)-(R)-2-((2S,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)-propan-2-yl)-5-methyltetrahydro-2H-pyran-2-yl)propan-1-ol
CAS No.:1333041-87-4
Molecular Formula:C₂₈H₄₂O₃Si
Molecular Weight:454.725
Hs Code.:

Synonyms:(+)-(R)-2-((2S,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)-propan-2-yl)-5-methyltetrahydro-2H-pyran-2-yl)propan-1-ol

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Chemical Property of (+)-(R)-2-((2S,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)-propan-2-yl)-5-methyltetrahydro-2H-pyran-2-yl)propan-1-ol

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Technology Process of (+)-(R)-2-((2S,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)-propan-2-yl)-5-methyltetrahydro-2H-pyran-2-yl)propan-1-ol

There total 1 articles about (+)-(R)-2-((2S,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)-propan-2-yl)-5-methyltetrahydro-2H-pyran-2-yl)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: 81.0%

: (+)-(S)-methyl 2-((2S,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-5-methyltetrahydro-2H-pyran-2-yl)propanoate

: 1333041-87-4
(+)-(R)-2-((2S,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)-propan-2-yl)-5-methyltetrahydro-2H-pyran-2-yl)propan-1-ol

Guidance literature:: (+)-(S)-methyl 2-((2S,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-5-methyltetrahydro-2H-pyran-2-yl)propanoate; With diisobutylaluminium hydride; In hexanes; dichloromethane; at -40 ℃; for 1h; Inert atmosphere;

With methanol; In hexanes; dichloromethane; at -40 ℃;
DOI:10.1021/jo2013884

Reference yield: 90.0%

: 2,2,2-benzyltrichloroacetimidate

: 1333041-87-4
(+)-(R)-2-((2S,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)-propan-2-yl)-5-methyltetrahydro-2H-pyran-2-yl)propan-1-ol

: 1333041-89-6
(+)-((S)-2-((2S,3S,6S)-6-((R)-1-(benzyloxy)propan-2-yl)-3-methyltetrahydro-2H-pyran-2-yl)propoxy)(tert-butyl)diphenylsilane

Guidance literature:: With trifluorormethanesulfonic acid; In dichloromethane; cyclohexane; at 0 ℃;
DOI:10.1021/jo2013884

Reference yield:

: 1333041-87-4
(+)-(R)-2-((2S,5S,6S)-6-((S)-1-(tert-butyldiphenylsilyloxy)-propan-2-yl)-5-methyltetrahydro-2H-pyran-2-yl)propan-1-ol

: 1333041-25-0
(3S,4S,5S,6S)-methyl 5-(benzyloxy)-6-((2S,3S,6S)-6-((R)-1-(benzyloxy)propan-2-yl)-3-methyltetrahydro-2H-pyran-2-yl)-2-bromo-3-hydroxy-2,4-dimethylheptanoate

Guidance literature:: Multi-step reaction with 9 steps

1.1: trifluorormethanesulfonic acid / dichloromethane; cyclohexane / 0 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere

2.2: Saturated solution

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

3.2: 1 h / -78 °C / Inert atmosphere

4.1: titanium(IV) trichloride isopropoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

4.2: Saturated solution

5.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / -78 °C / Inert atmosphere

5.2: -78 °C / Inert atmosphere

6.1: trifluorormethanesulfonic acid / dichloromethane; cyclohexane / 0 °C

7.1: diisobutylaluminium hydride / hexanes; dichloromethane / 1 h / -40 °C / Inert atmosphere

7.2: -40 °C

8.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere

9.1: titanium tetrachloride / dichloromethane / 1 h / -78 °C / Inert atmosphere

9.2: Saturated solution

With oxalyl dichloride; titanium(IV) trichloride isopropoxide; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; titanium tetrachloride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexanes; dichloromethane; cyclohexane; 3.1: Swern oxidation / 3.2: Swern oxidation / 4.1: Mukaiyama reaction / 9.1: Mukaiyama reaction;
DOI:10.1021/jo2013884