(2R,3R,5R,6S,7S)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-7-hydroxy-5-(p-methoxybenzyloxy)-4,4-dimethylcyclooctanone

Base Information

Chemical Name:(2R,3R,5R,6S,7S)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-7-hydroxy-5-(p-methoxybenzyloxy)-4,4-dimethylcyclooctanone
CAS No.:163380-51-6
Molecular Formula:C₃₈H₅₂O₇Si
Molecular Weight:648.912
Hs Code.:

Synonyms:(2R,3R,5R,6S,7S)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-7-hydroxy-5-(p-methoxybenzyloxy)-4,4-dimethylcyclooctanone

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Chemical Property of (2R,3R,5R,6S,7S)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-7-hydroxy-5-(p-methoxybenzyloxy)-4,4-dimethylcyclooctanone

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Technology Process of (2R,3R,5R,6S,7S)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-7-hydroxy-5-(p-methoxybenzyloxy)-4,4-dimethylcyclooctanone

There total 5 articles about (2R,3R,5R,6S,7S)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-7-hydroxy-5-(p-methoxybenzyloxy)-4,4-dimethylcyclooctanone 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: 62.0%

: 299938-97-9
(2R,3R,5R,6R)-2,6-Bis-benzyloxy-5,7-bis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-4,4-dimethyl-oct-7-enal

: 163226-90-2
(2R,3R,5R,6S,7R)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-7-hydroxy-5-(p-methoxybenzyloxy)-4,4-dimethylcyclooctanone

: 163380-51-6
(2R,3R,5R,6S,7S)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-7-hydroxy-5-(p-methoxybenzyloxy)-4,4-dimethylcyclooctanone

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at -45 ℃;
DOI:10.1246/cl.2000.932

Reference yield: 56.0%

: 163226-89-9
(2R,3R,5R,6R)-2,6-Dibenzyloxy-8-bromo-5-(tert-butyldimethylsiloxy)-3-(p-methoxybenzyloxy)-4,4-dimethyl-7-oxooctanal

: 163226-90-2
(2R,3R,5R,6S,7R)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-7-hydroxy-5-(p-methoxybenzyloxy)-4,4-dimethylcyclooctanone

: 163380-51-6
(2R,3R,5R,6S,7S)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-7-hydroxy-5-(p-methoxybenzyloxy)-4,4-dimethylcyclooctanone

Guidance literature:: With samarium diiodide; In tetrahydrofuran; at 0 ℃; for 0.5h;
DOI:10.1002/(sici)1521-3765(19990104)5:1<121::aid-chem121>3.3.co;2-f

Reference yield:

: 163226-84-4
(3R,4R,6R,7R)-3,7-Bis-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,5-dimethyl-8-phenylsulfanyl-8-trimethylsilanyloxy-octan-2-one

: 163380-51-6
(2R,3R,5R,6S,7S)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-7-hydroxy-5-(p-methoxybenzyloxy)-4,4-dimethylcyclooctanone

Guidance literature:: Multi-step reaction with 3 steps

1: lithium hexamethyldisilazide (LHMDS) / 0 °C

2: 76 percent / CuCl₂; tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / -78 °C

3: 8 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / -45 °C

With tetrabutyl ammonium fluoride; copper dichloride; lithium hexamethyldisilazane; In tetrahydrofuran; 1: silylation / 2: deacetalation / 3: Cyclization;
DOI:10.1246/cl.2000.932