4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-chloro-2,2-dimethyl-5-phenylselanyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol

Base Information

Chemical Name:4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-chloro-2,2-dimethyl-5-phenylselanyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol
CAS No.:1040272-24-9
Molecular Formula:C₂₁H₃₃ClO₄SeSi
Molecular Weight:491.989
Hs Code.:

Synonyms:4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-chloro-2,2-dimethyl-5-phenylselanyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol

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Chemical Property of 4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-chloro-2,2-dimethyl-5-phenylselanyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol

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Technology Process of 4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-chloro-2,2-dimethyl-5-phenylselanyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol

There total 5 articles about 4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-chloro-2,2-dimethyl-5-phenylselanyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol 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: 99.0%

: 5707-04-0
Phenylselenyl chloride

: 524939-62-6
4-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol

: 1040272-24-9
4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-chloro-2,2-dimethyl-5-phenylselanyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol

Guidance literature:: In acetonitrile; at 0 ℃; for 1h; Inert atmosphere;
DOI:10.1002/chem.200701998

Reference yield:

: 524939-60-4
(4R,5S)-(-)-1-(2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-2-(tert-butyldimethylsilyloxy)ethan-1-one

: 1040272-24-9
4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-chloro-2,2-dimethyl-5-phenylselanyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: magnesium / tetrahydrofuran / 16 h / 25 °C / Inert atmosphere

1.2: -78 - 25 °C / Inert atmosphere

1.3: -78 °C

2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 24 h / 25 °C / Inert atmosphere

3.1: acetonitrile / 1 h / 0 °C / Inert atmosphere

With magnesium; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; acetonitrile;

Reference yield:

: 75921-20-9
5-O-<(1,1-dimethylethyl)dimethylsilyl>-2,3-O-(1-methylethylidene)-β-D-ribofuranose

: 1040272-24-9
4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-chloro-2,2-dimethyl-5-phenylselanyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: potassium hexamethylsilazane / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

1.2: 48.5 h / 0 - 60 °C / Inert atmosphere

2.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 1 h / 0 - 25 °C / Inert atmosphere

3.1: magnesium / tetrahydrofuran / 16 h / 25 °C / Inert atmosphere

3.2: -78 - 25 °C / Inert atmosphere

3.3: -78 °C

4.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 24 h / 25 °C / Inert atmosphere

5.1: acetonitrile / 1 h / 0 °C / Inert atmosphere

With sulfur trioxide pyridine complex; potassium hexamethylsilazane; magnesium; dimethyl sulfoxide; triethylamine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; acetonitrile;