(2S,4S,5R,6S)-4-(benzyloxy)-6-[(4R,6R,8S)-9-(tert-butyldiphenylsiloxy)-8-hydroxy-6-[(p-methoxybenzyl)oxy]-4,7,7-trimethyl-3-oxo-2-(phenylsulfonyl)-3-nonyl]tetrahydro-3-methyl-2H-pyran-2-acetaldehyde

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Chemical Name:(2S,4S,5R,6S)-4-(benzyloxy)-6-[(4R,6R,8S)-9-(tert-butyldiphenylsiloxy)-8-hydroxy-6-[(p-methoxybenzyl)oxy]-4,7,7-trimethyl-3-oxo-2-(phenylsulfonyl)-3-nonyl]tetrahydro-3-methyl-2H-pyran-2-acetaldehyde
CAS No.:223693-05-8
Molecular Formula:C₅₇H₇₂O₁₀SSi
Molecular Weight:977.344
Hs Code.:

(2S,4S,5R,6S)-4-(benzyloxy)-6-[(4R,6R,8S)-9-(tert-butyldiphenylsiloxy)-8-hydroxy-6-[(p-methoxybenzyl)oxy]-4,7,7-trimethyl-3-oxo-2-(phenylsulfonyl)-3-nonyl]tetrahydro-3-methyl-2H-pyran-2-acetaldehyde

Synonyms:(2S,4S,5R,6S)-4-(benzyloxy)-6-[(4R,6R,8S)-9-(tert-butyldiphenylsiloxy)-8-hydroxy-6-[(p-methoxybenzyl)oxy]-4,7,7-trimethyl-3-oxo-2-(phenylsulfonyl)-3-nonyl]tetrahydro-3-methyl-2H-pyran-2-acetaldehyde

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Chemical Property of (2S,4S,5R,6S)-4-(benzyloxy)-6-[(4R,6R,8S)-9-(tert-butyldiphenylsiloxy)-8-hydroxy-6-[(p-methoxybenzyl)oxy]-4,7,7-trimethyl-3-oxo-2-(phenylsulfonyl)-3-nonyl]tetrahydro-3-methyl-2H-pyran-2-acetaldehyde

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Technology Process of (2S,4S,5R,6S)-4-(benzyloxy)-6-[(4R,6R,8S)-9-(tert-butyldiphenylsiloxy)-8-hydroxy-6-[(p-methoxybenzyl)oxy]-4,7,7-trimethyl-3-oxo-2-(phenylsulfonyl)-3-nonyl]tetrahydro-3-methyl-2H-pyran-2-acetaldehyde

There total 25 articles about (2S,4S,5R,6S)-4-(benzyloxy)-6-[(4R,6R,8S)-9-(tert-butyldiphenylsiloxy)-8-hydroxy-6-[(p-methoxybenzyl)oxy]-4,7,7-trimethyl-3-oxo-2-(phenylsulfonyl)-3-nonyl]tetrahydro-3-methyl-2H-pyran-2-acetaldehyde 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: 89.0%

: (4R,6R,8S)-2-Benzenesulfonyl-1-[(2S,4S,5R,6S)-4-benzyloxy-6-(2,3-dihydroxy-propyl)-5-methyl-tetrahydro-pyran-2-yl]-9-(tert-butyl-diphenyl-silanyloxy)-8-hydroxy-6-(4-methoxy-benzyloxy)-4,7,7-trimethyl-nonan-3-one

: 223693-05-8
(2S,4S,5R,6S)-4-(benzyloxy)-6-[(4R,6R,8S)-9-(tert-butyldiphenylsiloxy)-8-hydroxy-6-[(p-methoxybenzyl)oxy]-4,7,7-trimethyl-3-oxo-2-(phenylsulfonyl)-3-nonyl]tetrahydro-3-methyl-2H-pyran-2-acetaldehyde

Guidance literature:: With sodium periodate; In tetrahydrofuran; for 0.5h;
DOI:10.1021/ja993487o

Reference yield:

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

: 223693-05-8
(2S,4S,5R,6S)-4-(benzyloxy)-6-[(4R,6R,8S)-9-(tert-butyldiphenylsiloxy)-8-hydroxy-6-[(p-methoxybenzyl)oxy]-4,7,7-trimethyl-3-oxo-2-(phenylsulfonyl)-3-nonyl]tetrahydro-3-methyl-2H-pyran-2-acetaldehyde

Guidance literature:: Multi-step reaction with 11 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: 97 percent / p-TsOH / methanol / 1 h

10.1: OsO₄; NMO; water / tetrahydrofuran / 4 h

11.1: 89 percent / aq. NaIO₄ / tetrahydrofuran / 0.5 h

With 1H-imidazole; dmap; sodium periodate; 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); water; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; potassium hexacyanoferrate(III); potassium carbonate; In tetrahydrofuran; methanol; 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: desilylation / 10.1: dihydroxylation / 11.1: oxidative cleavage;
DOI:10.1021/ja993487o

Reference yield:

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

: 223693-05-8
(2S,4S,5R,6S)-4-(benzyloxy)-6-[(4R,6R,8S)-9-(tert-butyldiphenylsiloxy)-8-hydroxy-6-[(p-methoxybenzyl)oxy]-4,7,7-trimethyl-3-oxo-2-(phenylsulfonyl)-3-nonyl]tetrahydro-3-methyl-2H-pyran-2-acetaldehyde

Guidance literature:: Multi-step reaction with 10 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: 97 percent / p-TsOH / methanol / 1 h

9.1: OsO₄; NMO; water / tetrahydrofuran / 4 h

10.1: 89 percent / aq. NaIO₄ / tetrahydrofuran / 0.5 h

With 1H-imidazole; dmap; sodium periodate; 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); water; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; potassium hexacyanoferrate(III); potassium carbonate; In tetrahydrofuran; methanol; 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: desilylation / 9.1: dihydroxylation / 10.1: oxidative cleavage;
DOI:10.1021/ja993487o