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

Base Information

Chemical Name:(2R,3R,5R,6S,7S*,8R)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-7-hydroxy-5-(p-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone
CAS No.:253663-02-4
Molecular Formula:C₃₉H₅₄O₇Si
Molecular Weight:662.939
Hs Code.:

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

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Chemical Property of (2R,3R,5R,6S,7S*,8R)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-7-hydroxy-5-(p-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone

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Technology Process of (2R,3R,5R,6S,7S*,8R)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-7-hydroxy-5-(p-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone

There total 19 articles about (2R,3R,5R,6S,7S*,8R)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-7-hydroxy-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: 70.0%

: 194420-13-8
(2R,3R,5R,6R,8R*)-2,6-Dibenzyloxy-8-bromo-5-(tert-butyldimethylsiloxy)-3-(p-methoxybenzyloxy)-4,4-dimethyl-7-oxononanol

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

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

Guidance literature:: With samarium diiodide; In tetrahydrofuran; at -78 ℃; for 0.333333h;
DOI:10.1002/(sici)1521-3765(19990104)5:1<121::aid-chem121>3.3.co;2-f

Reference yield: 70.0%

: 253663-00-2
(2R,3R,5R,6R)-2,6-bis(benzyloxy)-5-(tert-butyldimethylsiloxy)-8-chloro-3-(4-methoxybenzyloxy)-4,4-dimethyl-7-oxononanal

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

Guidance literature:: dirhodium tetraacetate; In dichloromethane; for 1h; Heating;
DOI:10.1039/b000524j

Reference yield:

: 100-39-0
benzyl bromide

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

Guidance literature:: Multi-step reaction with 10 steps

1: 100 percent / NaH / dimethylformamide; tetrahydrofuran / 20 °C

2: 83 percent / BH₃*SMe₂ / tetrahydrofuran / 110 °C

3: 96 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 - 20 °C

4: 98 percent / MgBr₂*OEt₃ / toluene / -19 °C

5: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

6: 77 percent / nBuLi / hexane; diethyl ether; tetrahydrofuran / -100 - -78 °C

7: 90 percent / nBu₃SnH / benzene / Heating

8: 94 percent / aq. HCl / tetrahydrofuran / 20 °C

9: 92 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 - 20 °C

10: 65 percent / SmI₂ / tetrahydrofuran / 0 °C

With 2,6-dimethylpyridine; hydrogenchloride; n-butyllithium; samarium diiodide; oxalyl dichloride; dimethylsulfide borane complex; tri-n-butyl-tin hydride; sodium hydride; dimethyl sulfoxide; triethylamine; magnesium bromide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 1: benzylation / 2: Ring cleavage / 3: Swern oxidation / 4: aldol reaction / 5: silylation / 6: Substitution / 7: Dehalogenation / 8: desilylation / 9: Swern oxidation / 10: Cyclization;
DOI:10.1246/cl.1999.1145