(4R,6R)-4-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-6-((R)-1-hydroxypropan-2-yl)tetrahydro-2H-pyran-2-one

Base Information

Chemical Name:(4R,6R)-4-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-6-((R)-1-hydroxypropan-2-yl)tetrahydro-2H-pyran-2-one
CAS No.:423118-32-5
Molecular Formula:C₂₆H₃₆O₄Si
Molecular Weight:440.655
Hs Code.:

Synonyms:(4R,6R)-4-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-6-((R)-1-hydroxypropan-2-yl)tetrahydro-2H-pyran-2-one

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Chemical Property of (4R,6R)-4-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-6-((R)-1-hydroxypropan-2-yl)tetrahydro-2H-pyran-2-one

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Technology Process of (4R,6R)-4-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-6-((R)-1-hydroxypropan-2-yl)tetrahydro-2H-pyran-2-one

There total 25 articles about (4R,6R)-4-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-6-((R)-1-hydroxypropan-2-yl)tetrahydro-2H-pyran-2-one 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: 100.0%

: 423118-17-6
(1'R,4R,6R)-4-[2-(tert-butyldiphenylsilanyloxy)-ethyl]-6-[2'-(4-methoxybenzyloxy)-1'-methylethyl]-tetrahydropyran-2-one

: 423118-32-5
(4R,6R)-4-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-6-((R)-1-hydroxypropan-2-yl)tetrahydro-2H-pyran-2-one

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1039/b507570j

Reference yield: 82.0%

: (4R,6R)-6-((R)-1-(tert-butyldimethylsilyloxy)propan-2-yl)-4-(2-((tert-butyldiphenylsilyl)oxy)ethyl)tetrahydro-2H-pyran-2-one

: 423118-32-5
(4R,6R)-4-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-6-((R)-1-hydroxypropan-2-yl)tetrahydro-2H-pyran-2-one

Guidance literature:: With sodium periodate; In tetrahydrofuran; water; at 20 ℃; for 20h;
DOI:10.3390/molecules25194527

Reference yield:

: tert-butyldiphenyl-(5-vinylpent-3-enyloxy)-silane

: 423118-32-5
(4R,6R)-4-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-6-((R)-1-hydroxypropan-2-yl)tetrahydro-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 11 steps

1.1: 97 percent / toluene / 36 h / 170 °C

2.1: Bu₂BOTf; i-Pr₂NEt / CH₂Cl₂ / 0.5 h / -78 °C

2.2: 39 percent / CH₂Cl₂ / 2 h / -78 - 20 °C

3.1: 96 percent / LiBH₄ / methanol; diethyl ether / 2.5 h / 0 - 20 °C

4.1: 62 percent / camphorsulfonic acid / CH₂Cl₂ / 72 h / 0 °C

5.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

6.1: 82 percent / imidazole / CH₂Cl₂ / 2 h / 20 °C

7.1: 9-BBN / tetrahydrofuran / 12.5 h / 0 - 20 °C

7.2: 95 percent / aq. NaOH; H₂O₂ / tetrahydrofuran / 4 h / 0 °C

8.1: 96 percent / imidazole / CH₂Cl₂ / 2 h / 20 °C

9.1: 72 percent / pyridinium p-toluenesulfonate / ethanol / 2 h / 55 °C

10.1: 91 percent / Ag₂CO₃/celite / benzene / 3 h / 80 °C

11.1: 100 percent / aq. DDQ / CH₂Cl₂ / 2 h / 20 °C

With 1H-imidazole; lithium borohydride; 9-borabicyclo[3.3.1]nonane dimer; Celite; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; N-ethyl-N,N-diisopropylamine; silver carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; toluene; benzene; 1.1: Claisen rearrangement / 2.2: Evans aldol reaction;
DOI:10.1039/b507570j