(4S,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-6-trityloxymethyl-tetrahydro-pyran-2-one

Base Information

Chemical Name:(4S,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-6-trityloxymethyl-tetrahydro-pyran-2-one
CAS No.:871590-10-2
Molecular Formula:C₃₂H₄₀O₄Si
Molecular Weight:516.753
Hs Code.:

Synonyms:(4S,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-6-trityloxymethyl-tetrahydro-pyran-2-one

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Chemical Property of (4S,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-6-trityloxymethyl-tetrahydro-pyran-2-one

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Technology Process of (4S,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-6-trityloxymethyl-tetrahydro-pyran-2-one

There total 6 articles about (4S,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-6-trityloxymethyl-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: 98.0%

: 871590-06-6
(5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-trityloxymethyl-5,6-dihydro-pyran-2-one

: 15681-48-8
lithium dimethylcuprate

: 871590-10-2
(4S,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-6-trityloxymethyl-tetrahydro-pyran-2-one

Guidance literature:: In diethyl ether; at -40 ℃; for 2h;
DOI:10.1016/j.tetlet.2005.09.163

Reference yield:

: 5-(tert-butyl-dimethyl-silanyloxy)-6-trityloxymethyl-5,6-dihydro-2H-pyran-2-ol

: 871590-10-2
(4S,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-6-trityloxymethyl-tetrahydro-pyran-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 93 percent / TEMPO; Bu₄NCl; NCS / CH₂Cl₂ / 2 h / 23 °C / pH 8.6

2: 98 percent / diethyl ether / 2 h / -40 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; N-chloro-succinimide; tetrabutyl-ammonium chloride; In diethyl ether; dichloromethane;
DOI:10.1016/j.tetlet.2005.09.163

Reference yield:

: 871590-07-7
(2R,3R)-6-(3,4-Dimethoxy-benzyloxy)-2-trityloxymethyl-3,6-dihydro-2H-pyran-3-ol

: 871590-10-2
(4S,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-6-trityloxymethyl-tetrahydro-pyran-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: 99 percent / imidazole / dimethylformamide / 2 h / 23 °C

2: 80 percent / DDQ / CH₂Cl₂ / 0.5 h / 23 °C / pH 7

3: 93 percent / TEMPO; Bu₄NCl; NCS / CH₂Cl₂ / 2 h / 23 °C / pH 8.6

4: 98 percent / diethyl ether / 2 h / -40 °C

With 1H-imidazole; 2,2,6,6-tetramethyl-piperidine-N-oxyl; N-chloro-succinimide; tetrabutyl-ammonium chloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2005.09.163