(2R,3R,5R,6R,7R,8R)-7-Acetoxy-2,6-dibenzyloxy-3-(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone

Base Information

Chemical Name:(2R,3R,5R,6R,7R,8R)-7-Acetoxy-2,6-dibenzyloxy-3-(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone
CAS No.:222726-89-8
Molecular Formula:C₄₁H₅₆O₈Si
Molecular Weight:704.976
Hs Code.:

Synonyms:(2R,3R,5R,6R,7R,8R)-7-Acetoxy-2,6-dibenzyloxy-3-(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone

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Chemical Property of (2R,3R,5R,6R,7R,8R)-7-Acetoxy-2,6-dibenzyloxy-3-(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone

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Technology Process of (2R,3R,5R,6R,7R,8R)-7-Acetoxy-2,6-dibenzyloxy-3-(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone

There total 23 articles about (2R,3R,5R,6R,7R,8R)-7-Acetoxy-2,6-dibenzyloxy-3-(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone 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:

: 108-24-7
acetic anhydride

: 253663-02-4
(2R,3R,5R,6S,7S*,8R)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-7-hydroxy-5-(p-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone

: 222726-89-8
(2R,3R,5R,6R,7R,8R)-7-Acetoxy-2,6-dibenzyloxy-3-(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone

: 198711-88-5
(2R,3R,5R,6R,7S,8R)-7-Acetoxy-2,6-dibenzyloxy-3-(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone

Guidance literature:: With pyridine; dmap; at 20 ℃; for 1.5h;
DOI:10.1002/(sici)1521-3765(19990104)5:1<121::aid-chem121>3.3.co;2-f

Reference yield:

: 108-24-7
acetic anhydride

: 299939-00-7
(2R,3R,5R,6S,7R,8R)-2,6-bis(benzyloxy)-3-(t-butyldimethylsiloxy)-7-hydroxy-5-(4-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone

: 198711-92-1
(2R,3R,5R,6S,7S,8R)-2,6-bis(benzyloxy)-3-(t-butyldimethylsiloxy)-7-hydroxy-5-(4-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone

: 222726-89-8
(2R,3R,5R,6R,7R,8R)-7-Acetoxy-2,6-dibenzyloxy-3-(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone

: 198711-88-5
(2R,3R,5R,6R,7S,8R)-7-Acetoxy-2,6-dibenzyloxy-3-(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone

Guidance literature:: With dmap; In pyridine; at 0 - 20 ℃; for 1h;
DOI:10.1246/bcsj.74.113

Reference yield:

: 31600-43-8
methyl 2-(benzyloxy)acetate

: 222726-89-8
(2R,3R,5R,6R,7R,8R)-7-Acetoxy-2,6-dibenzyloxy-3-(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone

Guidance literature:: Multi-step reaction with 9 steps

1: 83 percent / hexamethyldisilazane; n-BuLi / hexane; tetrahydrofuran / -78 - 20 °C

2: 87 percent / MgBr₂*Et₂O / toluene / 1 h / -19 °C

3: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

4: 78 percent / n-BuLi / hexane; diethyl ether; tetrahydrofuran / 1 h / -100 - -78 °C

5: 90 percent / Bu₃SnH / benzene / 0.5 h / Heating

6: 93 percent / aq. HCl / tetrahydrofuran / 12 h / 0 - 20 °C

7: 92 percent / oxalyl chloride; DMSO / CH₂Cl₂ / -78 - 20 °C

8: SmI₂ / tetrahydrofuran / 0.33 h / -23 °C

9: DMAP / pyridine / 1 h / 0 - 20 °C

With 2,6-dimethylpyridine; hydrogenchloride; dmap; n-butyllithium; samarium diiodide; oxalyl dichloride; tri-n-butyl-tin hydride; dimethyl sulfoxide; 1,1,1,3,3,3-hexamethyl-disilazane; magnesium bromide; In tetrahydrofuran; pyridine; diethyl ether; hexane; dichloromethane; toluene; benzene; 7: Swern's oxidation;
DOI:10.1246/bcsj.74.113