(3R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-pyran-2-one

Base Information

Chemical Name:(3R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-pyran-2-one
CAS No.:243464-43-9
Molecular Formula:C₂₂H₂₈O₄Si
Molecular Weight:384.547
Hs Code.:

Synonyms:(3R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-pyran-2-one

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Chemical Property of (3R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-pyran-2-one

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Technology Process of (3R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-pyran-2-one

There total 3 articles about (3R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-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:

: 106731-74-2,119944-29-5,107033-46-5
tert-butyl[(2S)-oxiran-2-ylmethoxy]diphenylsilane

: 243464-43-9
(3R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-pyran-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 0.25 h / -78 °C

1.2: 93 percent / boron trifluoride diethyl etherate / hexane; tetrahydrofuran / 0.67 h / -78 °C

2.1: 78 percent / H₂ / Pd/C / ethyl acetate / 6 h / 760.05 Torr

3.1: 75 percent / PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 22 h / 20 °C

4.1: LDA; TMEDA / hexane; tetrahydrofuran / 0.5 h / -78 °C

4.2: 61 percent / (+)-(2R,8S)-camphorsulfonyloxaziridine / tetrahydrofuran; hexane / -78 - -40 °C

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; 4 A molecular sieve; hydrogen; pyridinium chlorochromate; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate;
DOI:10.1021/jo001433n

Reference yield:

: 243464-44-0
(2S)-6-benzyloxy-1-(tert-butyldiphenylsilyloxy)-hex-4-yn-2-ol

: 243464-43-9
(3R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-pyran-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 78 percent / H₂ / Pd/C / ethyl acetate / 6 h / 760.05 Torr

2.1: 75 percent / PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 22 h / 20 °C

3.1: LDA; TMEDA / hexane; tetrahydrofuran / 0.5 h / -78 °C

3.2: 61 percent / (+)-(2R,8S)-camphorsulfonyloxaziridine / tetrahydrofuran; hexane / -78 - -40 °C

With N,N,N,N,-tetramethylethylenediamine; 4 A molecular sieve; hydrogen; pyridinium chlorochromate; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate;
DOI:10.1021/jo001433n

Reference yield:

: 243464-45-1
(S)-6-(tert-butyl-diphenylsilyloxy)-hexane-1,5-diol

: 243464-43-9
(3R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-pyran-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: 75 percent / PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 22 h / 20 °C

2.1: LDA; TMEDA / hexane; tetrahydrofuran / 0.5 h / -78 °C

2.2: 61 percent / (+)-(2R,8S)-camphorsulfonyloxaziridine / tetrahydrofuran; hexane / -78 - -40 °C

With N,N,N,N,-tetramethylethylenediamine; 4 A molecular sieve; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/jo001433n