(4R,6R,8S)-1-[(2S,4S,5R,6S)-6-allyl-4-(benzyloxy)tetrahydro-5-methyl-2H-pyran-2-yl]-9-(tert-butyldiphenylsiloxy)-6-[(p-methoxybenzyl)oxy]-4,7,7-trimethyl-8-(triethylsiloxy)-2,3-nonanedione

Base Information

Chemical Name:(4R,6R,8S)-1-[(2S,4S,5R,6S)-6-allyl-4-(benzyloxy)tetrahydro-5-methyl-2H-pyran-2-yl]-9-(tert-butyldiphenylsiloxy)-6-[(p-methoxybenzyl)oxy]-4,7,7-trimethyl-8-(triethylsiloxy)-2,3-nonanedione
CAS No.:261374-49-6
Molecular Formula:C₅₈H₈₂O₈Si₂
Molecular Weight:963.455
Hs Code.:

(4R,6R,8S)-1-[(2S,4S,5R,6S)-6-allyl-4-(benzyloxy)tetrahydro-5-methyl-2H-pyran-2-yl]-9-(tert-butyldiphenylsiloxy)-6-[(p-methoxybenzyl)oxy]-4,7,7-trimethyl-8-(triethylsiloxy)-2,3-nonanedione

Synonyms:(4R,6R,8S)-1-[(2S,4S,5R,6S)-6-allyl-4-(benzyloxy)tetrahydro-5-methyl-2H-pyran-2-yl]-9-(tert-butyldiphenylsiloxy)-6-[(p-methoxybenzyl)oxy]-4,7,7-trimethyl-8-(triethylsiloxy)-2,3-nonanedione

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Chemical Property of (4R,6R,8S)-1-[(2S,4S,5R,6S)-6-allyl-4-(benzyloxy)tetrahydro-5-methyl-2H-pyran-2-yl]-9-(tert-butyldiphenylsiloxy)-6-[(p-methoxybenzyl)oxy]-4,7,7-trimethyl-8-(triethylsiloxy)-2,3-nonanedione

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Technology Process of (4R,6R,8S)-1-[(2S,4S,5R,6S)-6-allyl-4-(benzyloxy)tetrahydro-5-methyl-2H-pyran-2-yl]-9-(tert-butyldiphenylsiloxy)-6-[(p-methoxybenzyl)oxy]-4,7,7-trimethyl-8-(triethylsiloxy)-2,3-nonanedione

There total 22 articles about (4R,6R,8S)-1-[(2S,4S,5R,6S)-6-allyl-4-(benzyloxy)tetrahydro-5-methyl-2H-pyran-2-yl]-9-(tert-butyldiphenylsiloxy)-6-[(p-methoxybenzyl)oxy]-4,7,7-trimethyl-8-(triethylsiloxy)-2,3-nonanedione 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:

: 215317-64-9
(3R,5R)-5-(1-(tert-butyldiphenylsilyloxy)-2-methylpropan-2-yl)-3-methyldihydrofuran-2(3H)-one

: 261374-49-6
(4R,6R,8S)-1-[(2S,4S,5R,6S)-6-allyl-4-(benzyloxy)tetrahydro-5-methyl-2H-pyran-2-yl]-9-(tert-butyldiphenylsiloxy)-6-[(p-methoxybenzyl)oxy]-4,7,7-trimethyl-8-(triethylsiloxy)-2,3-nonanedione

Guidance literature:: Multi-step reaction with 14 steps

1.1: 93 percent / LiBH₄ / diethyl ether; methanol / 0.5 h / 0 °C

2.1: 96 percent / pyridine / CH₂Cl₂ / 25 °C

3.1: 81 percent / triflic acid / diethyl ether / 1 h / 20 °C

4.1: 94 percent / TBAF / tetrahydrofuran / 72 h

5.1: 99 percent / DMSO; oxalyl chloride / CH₂Cl₂ / 1 h / -78 °C

6.1: potassium hexamethyldisilazide / toluene; tetrahydrofuran / 0.33 h / 0 °C

6.2: 89 percent / tetrahydrofuran; toluene / 0.33 h / 0 °C

7.1: 99 percent / (DHQ)2PYR; OsO₄; K₃Fe(CN)6 / K₂CO₃ / H₂O; 2-methyl-propan-2-ol / 0 °C

8.1: 636 mg / imidazole / tetrahydrofuran / 5 h

9.1: 439 mg / DMAP; imidazole / dimethylformamide / 5 h

10.1: 79 percent / Dibal-H / tetrahydrofuran; hexane / 1 h / -40 °C

11.1: 89 percent / tetra-n-propylammonium perruthenate; NMO; 4A MS / CH₂Cl₂ / 1 h

12.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

12.2: 76 percent / tetrahydrofuran; hexane / 0.33 h / -78 °C

13.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h

14.1: potassium tert-butoxide / tetrahydrofuran; 2-methyl-propan-2-ol / 0.25 h

14.2: 79 percent / Davis oxiziridine / tetrahydrofuran; 2-methyl-propan-2-ol / 0.5 h / 0 °C

With pyridine; 1H-imidazole; dmap; osmium(VIII) oxide; lithium borohydride; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; oxalyl dichloride; (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); trifluorormethanesulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; potassium hexacyanoferrate(III); potassium carbonate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1.1: Ring cleavage / 2.1: Esterification / 3.1: benzylation / 4.1: desilylation / 5.1: Swern oxidation / 6.1: Metallation / 6.2: Wittig olefination / 7.1: hydroxylation / 8.1: silylation / 9.1: silylation / 10.1: reductive deacylation / 11.1: Oxidation / 12.1: Metallation / 12.2: Addition / 13.1: Oxidation / 14.1: deprotonation / 14.2: oxidative desulfonylation;
DOI:10.1021/ja993487o

Reference yield:

: 223693-16-1
(2R,4R)-[(p-methoxybenzyl)oxy]-2,5,5-trimethyl-6-heptenyl pivalate

: 261374-49-6
(4R,6R,8S)-1-[(2S,4S,5R,6S)-6-allyl-4-(benzyloxy)tetrahydro-5-methyl-2H-pyran-2-yl]-9-(tert-butyldiphenylsiloxy)-6-[(p-methoxybenzyl)oxy]-4,7,7-trimethyl-8-(triethylsiloxy)-2,3-nonanedione

Guidance literature:: Multi-step reaction with 8 steps

1.1: 99 percent / (DHQ)2PYR; OsO₄; K₃Fe(CN)6 / K₂CO₃ / H₂O; 2-methyl-propan-2-ol / 0 °C

2.1: 636 mg / imidazole / tetrahydrofuran / 5 h

3.1: 439 mg / DMAP; imidazole / dimethylformamide / 5 h

4.1: 79 percent / Dibal-H / tetrahydrofuran; hexane / 1 h / -40 °C

5.1: 89 percent / tetra-n-propylammonium perruthenate; NMO; 4A MS / CH₂Cl₂ / 1 h

6.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

6.2: 76 percent / tetrahydrofuran; hexane / 0.33 h / -78 °C

7.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h

8.1: potassium tert-butoxide / tetrahydrofuran; 2-methyl-propan-2-ol / 0.25 h

8.2: 79 percent / Davis oxiziridine / tetrahydrofuran; 2-methyl-propan-2-ol / 0.5 h / 0 °C

With 1H-imidazole; dmap; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); potassium tert-butylate; diisobutylaluminium hydride; Dess-Martin periodane; potassium hexacyanoferrate(III); potassium carbonate; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: hydroxylation / 2.1: silylation / 3.1: silylation / 4.1: reductive deacylation / 5.1: Oxidation / 6.1: Metallation / 6.2: Addition / 7.1: Oxidation / 8.1: deprotonation / 8.2: oxidative desulfonylation;
DOI:10.1021/ja993487o

Reference yield:

: 223693-00-3
(2R,4R)-5-formyl-4-[(p-methoxybenzyl)oxy]-2,5-dimethylhexyl pivalate

: 261374-49-6
(4R,6R,8S)-1-[(2S,4S,5R,6S)-6-allyl-4-(benzyloxy)tetrahydro-5-methyl-2H-pyran-2-yl]-9-(tert-butyldiphenylsiloxy)-6-[(p-methoxybenzyl)oxy]-4,7,7-trimethyl-8-(triethylsiloxy)-2,3-nonanedione

Guidance literature:: Multi-step reaction with 9 steps

1.1: potassium hexamethyldisilazide / toluene; tetrahydrofuran / 0.33 h / 0 °C

1.2: 89 percent / tetrahydrofuran; toluene / 0.33 h / 0 °C

2.1: 99 percent / (DHQ)2PYR; OsO₄; K₃Fe(CN)6 / K₂CO₃ / H₂O; 2-methyl-propan-2-ol / 0 °C

3.1: 636 mg / imidazole / tetrahydrofuran / 5 h

4.1: 439 mg / DMAP; imidazole / dimethylformamide / 5 h

5.1: 79 percent / Dibal-H / tetrahydrofuran; hexane / 1 h / -40 °C

6.1: 89 percent / tetra-n-propylammonium perruthenate; NMO; 4A MS / CH₂Cl₂ / 1 h

7.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

7.2: 76 percent / tetrahydrofuran; hexane / 0.33 h / -78 °C

8.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h

9.1: potassium tert-butoxide / tetrahydrofuran; 2-methyl-propan-2-ol / 0.25 h

9.2: 79 percent / Davis oxiziridine / tetrahydrofuran; 2-methyl-propan-2-ol / 0.5 h / 0 °C

With 1H-imidazole; dmap; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); potassium tert-butylate; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; potassium hexacyanoferrate(III); potassium carbonate; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1.1: Metallation / 1.2: Wittig olefination / 2.1: hydroxylation / 3.1: silylation / 4.1: silylation / 5.1: reductive deacylation / 6.1: Oxidation / 7.1: Metallation / 7.2: Addition / 8.1: Oxidation / 9.1: deprotonation / 9.2: oxidative desulfonylation;
DOI:10.1021/ja993487o