(1R,2R,3S,4S,5S)-acetic acid 2-tert-butoxy-1-(tert-butyldiphenyl-silanyloxymethyl)-3,4-dihydroxy bicyclo[3.1.0]hex-3-ylmethyl ester

Base Information

Chemical Name:(1R,2R,3S,4S,5S)-acetic acid 2-tert-butoxy-1-(tert-butyldiphenyl-silanyloxymethyl)-3,4-dihydroxy bicyclo[3.1.0]hex-3-ylmethyl ester
CAS No.:1355670-53-9
Molecular Formula:C₃₀H₄₂O₆Si
Molecular Weight:526.745
Hs Code.:

Synonyms:(1R,2R,3S,4S,5S)-acetic acid 2-tert-butoxy-1-(tert-butyldiphenyl-silanyloxymethyl)-3,4-dihydroxy bicyclo[3.1.0]hex-3-ylmethyl ester

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Chemical Property of (1R,2R,3S,4S,5S)-acetic acid 2-tert-butoxy-1-(tert-butyldiphenyl-silanyloxymethyl)-3,4-dihydroxy bicyclo[3.1.0]hex-3-ylmethyl ester

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Technology Process of (1R,2R,3S,4S,5S)-acetic acid 2-tert-butoxy-1-(tert-butyldiphenyl-silanyloxymethyl)-3,4-dihydroxy bicyclo[3.1.0]hex-3-ylmethyl ester

There total 8 articles about (1R,2R,3S,4S,5S)-acetic acid 2-tert-butoxy-1-(tert-butyldiphenyl-silanyloxymethyl)-3,4-dihydroxy bicyclo[3.1.0]hex-3-ylmethyl ester 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: 83.0%

: 1355670-50-6
(1R,2R,3R,4S,5S)-acetic acid 2-tert-butoxy-4-(tert-butyldimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-bicyclo[3.1.0]hex-3-ylmethyl ester

: 1355670-53-9
(1R,2R,3S,4S,5S)-acetic acid 2-tert-butoxy-1-(tert-butyldiphenyl-silanyloxymethyl)-3,4-dihydroxy bicyclo[3.1.0]hex-3-ylmethyl ester

Guidance literature:: With pyridinium p-toluenesulfonate; In ethanol; at 55 ℃; for 48h;
DOI:10.1016/j.tet.2011.11.052

Reference yield:

: 1355670-44-8
(1R,2R,3R,4S,5S)-2-tert-butoxy-4-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxymethyl)-bicyclo[3.1.0]hexan-3-ol

: 1355670-53-9
(1R,2R,3S,4S,5S)-acetic acid 2-tert-butoxy-1-(tert-butyldiphenyl-silanyloxymethyl)-3,4-dihydroxy bicyclo[3.1.0]hex-3-ylmethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C

1.2: 1 h / -78 - 20 °C

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.5 h / 0 - 20 °C

2.2: 5 h / 0 - 20 °C

3.1: tetrabutylammonium acetate / 48 h / 100 °C

4.1: pyridinium p-toluenesulfonate / ethanol / 48 h / 55 °C

With oxalyl dichloride; tetrabutylammonium acetate; pyridinium p-toluenesulfonate; dimethyl sulfoxide; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; 1.1: Swern oxidation / 1.2: Swern oxidation;
DOI:10.1016/j.tet.2011.11.052

Reference yield:

: 915694-39-2
(+)-(1S,2S,3S,4R,5R)-4-tert-butoxy-5-(tert-butyldiphenylsilyloxymethyl)bicyclo[3.1.0]hexane-2,3-diol

: 1355670-53-9
(1R,2R,3S,4S,5S)-acetic acid 2-tert-butoxy-1-(tert-butyldiphenyl-silanyloxymethyl)-3,4-dihydroxy bicyclo[3.1.0]hex-3-ylmethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 1H-imidazole / dichloromethane / 0 - 20 °C

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C

2.2: 1 h / -78 - 20 °C

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.5 h / 0 - 20 °C

3.2: 5 h / 0 - 20 °C

4.1: tetrabutylammonium acetate / 48 h / 100 °C

5.1: pyridinium p-toluenesulfonate / ethanol / 48 h / 55 °C

With 1H-imidazole; oxalyl dichloride; tetrabutylammonium acetate; pyridinium p-toluenesulfonate; dimethyl sulfoxide; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; 2.1: Swern oxidation / 2.2: Swern oxidation;
DOI:10.1016/j.tet.2011.11.052