(3S,4S,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-3,4-dimethyl-6-trityloxymethyl-tetrahydro-pyran-2-one

Base Information

Chemical Name:(3S,4S,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-3,4-dimethyl-6-trityloxymethyl-tetrahydro-pyran-2-one
CAS No.:871590-11-3
Molecular Formula:C₃₃H₄₂O₄Si
Molecular Weight:530.78
Hs Code.:

Synonyms:(3S,4S,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-3,4-dimethyl-6-trityloxymethyl-tetrahydro-pyran-2-one

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

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

There total 7 articles about (3S,4S,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-3,4-dimethyl-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%

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

: 74-88-4
methyl iodide

: 871590-11-3
(3S,4S,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-3,4-dimethyl-6-trityloxymethyl-tetrahydro-pyran-2-one

Guidance literature:: With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h;
DOI:10.1016/j.tetlet.2005.09.163

Reference yield:

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

: 871590-11-3
(3S,4S,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-3,4-dimethyl-6-trityloxymethyl-tetrahydro-pyran-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 98 percent / diethyl ether / 2 h / -40 °C

2: 98 percent / NaHMDS / tetrahydrofuran / 0.5 h / -78 °C

With sodium hexamethyldisilazane; In tetrahydrofuran; diethyl ether;
DOI:10.1016/j.tetlet.2005.09.163

Reference yield:

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

: 871590-11-3
(3S,4S,5R,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-3,4-dimethyl-6-trityloxymethyl-tetrahydro-pyran-2-one

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: 98 percent / NaHMDS / tetrahydrofuran / 0.5 h / -78 °C

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