(1S,4R,5R_.7R,9S,13S,14R,15S)-15-(benzyloxy)-9-[(tert-butyldiphenylsiloxy)methyl]-4-hydroxy-5,8,8,14-tetramethyl-10,17,18-trioxatricyclo[11.3.1.1^4,7]octadecane-3,11-dione

Base Information

• Chemical Name: (1S,4R,5R_.7R,9S,13S,14R,15S)-15-(benzyloxy)-9-[(tert-butyldiphenylsiloxy)methyl]-4-hydroxy-5,8,8,14-tetramethyl-10,17,18-trioxatricyclo[11.3.1.1^4,7]octadecane-3,11-dione
• CAS No.: 261374-52-1
• Molecular Formula: C₄₃H₅₆O₈Si
• Molecular Weight: 728.998

Synonyms:(1S,4R,5R_.7R,9S,13S,14R,15S)-15-(benzyloxy)-9-[(tert-butyldiphenylsiloxy)methyl]-4-hydroxy-5,8,8,14-tetramethyl-10,17,18-trioxatricyclo[11.3.1.1^4,7]octadecane-3,11-dione

Chemical Property of (1S,4R,5R_.7R,9S,13S,14R,15S)-15-(benzyloxy)-9-[(tert-butyldiphenylsiloxy)methyl]-4-hydroxy-5,8,8,14-tetramethyl-10,17,18-trioxatricyclo[11.3.1.1^4,7]octadecane-3,11-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4R,5R_.7R,9S,13S,14R,15S)-15-(benzyloxy)-9-[(tert-butyldiphenylsiloxy)methyl]-4-hydroxy-5,8,8,14-tetramethyl-10,17,18-trioxatricyclo[11.3.1.1^4,7]octadecane-3,11-dione

There total 29 articles about (1S,4R,5R_.7R,9S,13S,14R,15S)-15-(benzyloxy)-9-[(tert-butyldiphenylsiloxy)methyl]-4-hydroxy-5,8,8,14-tetramethyl-10,17,18-trioxatricyclo[11.3.1.1^4,7]octadecane-3,11-dione 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: 63.0%

(1S,5S,7R,9R,13S,15S,16R)-15-(benzyloxy)-5-[(tert-butyldiphenylsiloxy)methyl]-7-[(p-methoxybenzyl)oxy]-6,6,9,16-tetramethyl-4,17-dioxabicyclo[11.3.1]heptadecane-3,10,11-trione (261374-51-0) → (1S,4R,5R.7R,9S,13S,14R,15S)-15-(benzyloxy)-9-[(tert-butyldiphenylsiloxy)methyl]-4-hydroxy-5,8,8,14-tetramethyl-10,17,18-trioxatricyclo[11.3.1.14,7]octadecane-3,11-dione (261374-52-1)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; for 2h;

DOI:10.1021/ja993487o

Reference yield:

(3R,5R)-5-(1-(tert-butyldiphenylsilyloxy)-2-methylpropan-2-yl)-3-methyldihydrofuran-2(3H)-one (215317-64-9) → (1S,4R,5R.7R,9S,13S,14R,15S)-15-(benzyloxy)-9-[(tert-butyldiphenylsiloxy)methyl]-4-hydroxy-5,8,8,14-tetramethyl-10,17,18-trioxatricyclo[11.3.1.14,7]octadecane-3,11-dione (261374-52-1)

Guidance literature:

Multi-step reaction with 21 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: 97 percent / p-TsOH / methanol / 1 h

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

16.1: 89 percent / aq. NaIO₄ / tetrahydrofuran / 0.5 h

17.1: 88 percent / aq. NaH₂PO₄; NaClO₂; 2-methyl-2-butene / H₂O; 2-methyl-propan-2-ol / 0.17 h / 0 °C

18.1: NEt₃ / tetrahydrofuran / 4 h / 25 °C

19.1: 82 percent / DMAP / tetrahydrofuran; toluene / 0.5 h / 110 °C

20.1: potassium tert-butoxide / CH₂Cl₂; 2-methyl-propan-2-ol / 0.33 h / 0 °C

20.2: 70 percent / Davis oxaziridine / tetrahydrofuran; 2-methyl-propan-2-ol / 0.17 h / 0 °C

21.1: 63 percent / DDQ / CH₂Cl₂; H₂O / 2 h

With pyridine; 1H-imidazole; dmap; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; lithium borohydride; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; 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; water; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 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: desilylation / 15.1: dihydroxylation / 16.1: oxidative cleavage / 17.1: Oxidation / 18.1: Condensation / 19.1: Cyclization / 20.1: deprotonation / 20.2: oxidative desulfonylation / 21;

DOI:10.1021/ja993487o

Reference yield:

(2R,4R)-5-formyl-4-[(p-methoxybenzyl)oxy]-2,5-dimethylhexyl pivalate (223693-00-3) → (1S,4R,5R.7R,9S,13S,14R,15S)-15-(benzyloxy)-9-[(tert-butyldiphenylsiloxy)methyl]-4-hydroxy-5,8,8,14-tetramethyl-10,17,18-trioxatricyclo[11.3.1.14,7]octadecane-3,11-dione (261374-52-1)

Guidance literature:

Multi-step reaction with 16 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

12.1: 88 percent / aq. NaH₂PO₄; NaClO₂; 2-methyl-2-butene / H₂O; 2-methyl-propan-2-ol / 0.17 h / 0 °C

13.1: NEt₃ / tetrahydrofuran / 4 h / 25 °C

14.1: 82 percent / DMAP / tetrahydrofuran; toluene / 0.5 h / 110 °C

15.1: potassium tert-butoxide / CH₂Cl₂; 2-methyl-propan-2-ol / 0.33 h / 0 °C

15.2: 70 percent / Davis oxaziridine / tetrahydrofuran; 2-methyl-propan-2-ol / 0.17 h / 0 °C

16.1: 63 percent / DDQ / CH₂Cl₂; H₂O / 2 h

With 1H-imidazole; dmap; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; (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; water; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 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 / 12.1: Oxidation / 13.1: Condensation / 14.1: Cyclization / 15.1: deprotonation / 15.2: oxidative desulfonylation / 16.1: transannular cyclization;

DOI:10.1021/ja993487o

upstream raw materials:

(1S,5S,7R,9R,13S,15S,16R)-15-(benzyloxy)-5-[(tert-butyldiphenylsiloxy)methyl]-7-[(p-methoxybenzyl)oxy]-6,6,9,16-tetramethyl-4,17-dioxabicyclo[11.3.1]heptadecane-3,10,11-trione

benzyl bromide

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

(2S,4S,5R,6S)-6-allyl-4-(benzyloxy)tetrahydro-5-methyl-2H-pyran-2-methanol

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