(3R,4S,5S,6S)-6-(2-Benzyloxy-ethyl)-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-tetrahydro-pyran-2-one

Base Information

Chemical Name:(3R,4S,5S,6S)-6-(2-Benzyloxy-ethyl)-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-tetrahydro-pyran-2-one
CAS No.:201054-38-8
Molecular Formula:C₂₂H₃₆O₄Si
Molecular Weight:392.611
Hs Code.:

Synonyms:(3R,4S,5S,6S)-6-(2-Benzyloxy-ethyl)-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-tetrahydro-pyran-2-one

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Chemical Property of (3R,4S,5S,6S)-6-(2-Benzyloxy-ethyl)-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-tetrahydro-pyran-2-one

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Technology Process of (3R,4S,5S,6S)-6-(2-Benzyloxy-ethyl)-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-tetrahydro-pyran-2-one

There total 5 articles about (3R,4S,5S,6S)-6-(2-Benzyloxy-ethyl)-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-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: 85.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 201054-36-6
(3R,4S,5R,6S)-6-(2-Benzyloxy-ethyl)-4-hydroxy-3,5-dimethyl-tetrahydro-pyran-2-one

: 201054-38-8
(3R,4S,5S,6S)-6-(2-Benzyloxy-ethyl)-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-tetrahydro-pyran-2-one

Guidance literature:: With 1H-imidazole; dmap; In N,N-dimethyl-formamide;
DOI:10.1246/cl.1997.1191

Reference yield:

: 149916-84-7
(E)-(4R,5S)-7-Benzyloxy-5-hydroxy-4-methyl-hept-2-enoic acid ethyl ester

: 201054-38-8
(3R,4S,5S,6S)-6-(2-Benzyloxy-ethyl)-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-tetrahydro-pyran-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: 93 percent / t-BuOK / tetrahydrofuran / 0 °C

2: 85 percent / 70percent acetic acid / tetrahydrofuran; H₂O / 90 °C

3: 78 percent / LDA / tetrahydrofuran / -50 °C

4: 85 percent / DMAP, imidazole / dimethylformamide

With 1H-imidazole; dmap; potassium tert-butylate; acetic acid; lithium diisopropyl amide; In tetrahydrofuran; water; N,N-dimethyl-formamide;
DOI:10.1246/cl.1997.1191

Reference yield:

: 201054-30-0
(4R,5R,6S)-6-(2-Benzyloxy-ethyl)-4-hydroxy-5-methyl-tetrahydro-pyran-2-one

: 201054-38-8
(3R,4S,5S,6S)-6-(2-Benzyloxy-ethyl)-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-tetrahydro-pyran-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 78 percent / LDA / tetrahydrofuran / -50 °C

2: 85 percent / DMAP, imidazole / dimethylformamide

With 1H-imidazole; dmap; lithium diisopropyl amide; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1246/cl.1997.1191