<3R,4S,5S,9S,10R,11R>-9-hydroxy-3-methoxy-5-<(p-methoxybenzyl)oxy>-6,6,10-trimethyl-7-oxo-4,11-bis(triethylsiloxy)-12-tridecenyl pivalate

Base Information

• Chemical Name: <3R,4S,5S,9S,10R,11R>-9-hydroxy-3-methoxy-5-<(p-methoxybenzyl)oxy>-6,6,10-trimethyl-7-oxo-4,11-bis(triethylsiloxy)-12-tridecenyl pivalate
• CAS No.: 131698-92-5
• Molecular Formula: C₄₂H₇₆O₉Si₂
• Molecular Weight: 781.231
• Mol file: 131698-92-5.mol

Synonyms:<3R,4S,5S,9S,10R,11R>-9-hydroxy-3-methoxy-5-<(p-methoxybenzyl)oxy>-6,6,10-trimethyl-7-oxo-4,11-bis(triethylsiloxy)-12-tridecenyl pivalate

Chemical Property of <3R,4S,5S,9S,10R,11R>-9-hydroxy-3-methoxy-5-<(p-methoxybenzyl)oxy>-6,6,10-trimethyl-7-oxo-4,11-bis(triethylsiloxy)-12-tridecenyl pivalate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <3R,4S,5S,9S,10R,11R>-9-hydroxy-3-methoxy-5-<(p-methoxybenzyl)oxy>-6,6,10-trimethyl-7-oxo-4,11-bis(triethylsiloxy)-12-tridecenyl pivalate

There total 21 articles about <3R,4S,5S,9S,10R,11R>-9-hydroxy-3-methoxy-5-<(p-methoxybenzyl)oxy>-6,6,10-trimethyl-7-oxo-4,11-bis(triethylsiloxy)-12-tridecenyl pivalate 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:

<4S>-4-benzyl-3-(3,3,4-trimethyl-4-pentenoyl)-2-oxazolidinone (139426-78-1) → <3R,4S,5S,9S,10R,11R>-9-hydroxy-3-methoxy-5-<(p-methoxybenzyl)oxy>-6,6,10-trimethyl-7-oxo-4,11-bis(triethylsiloxy)-12-tridecenyl pivalate (131698-92-5)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) NaHMDS, 2.) 2-(phenylsulfonyl)-3-phenyloxaziridine / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C

2: 1.) AlMe₃ / 1.) CH₂Cl₂, toluene, 25 deg C, 30 min, 2.) CH₂Cl₂, toluene, reflux, 24 h

3: 1.) NaH / 1.) DMF, THF, 15 min, 2.) DMF, THF, 5 min

4: 93 percent / DIBAL-H / toluene / -78 °C

5: 71 percent / MgBr₂*Et₂O / CH₂Cl₂ / 1 h / -20 °C

6: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

7: 1.) tris(triphenylphosphine)rhodium(I) chloride, catecholborane, 2.) 2M NaOH, 30percent aq. H₂O₂ / 1.) THF, 50 min, 2.) THF, EtOH, a) 0 deg C, 30 min, b) from 0 deg C to RT, 30 min

8: 89 percent / DMAP, pyridine / CH₂Cl₂

9: 1.) N-methylmorpholine N-oxide, OsO₄, 2.) NaIO₄ / 1.) t-BuOH, THF, H₂O, 20 h, 2.) t-BuOH, THF, H₂O, 20 h

10: 99 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

11: 80 percent / BF₃*Et₂O / CH₂Cl₂ / 8 h / -78 °C

With pyridine; 2,6-dimethylpyridine; dmap; sodium hydroxide; sodium periodate; Wilkinson's catalyst; osmium(VIII) oxide; boron trifluoride diethyl etherate; dihydrogen peroxide; trimethylaluminum; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; N-(benzenesulfonyl)-3-phenyloxaziridine; triethylamine; magnesium bromide; benzo[1,3,2]dioxaborole; In dichloromethane; toluene;

DOI:10.1021/ja00050a024

Reference yield:

(S)-2-(4-Methoxy-benzyloxy)-3,3,4-trimethyl-pent-4-enal (139426-80-5) → <3R,4S,5S,9S,10R,11R>-9-hydroxy-3-methoxy-5-<(p-methoxybenzyl)oxy>-6,6,10-trimethyl-7-oxo-4,11-bis(triethylsiloxy)-12-tridecenyl pivalate (131698-92-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 71 percent / MgBr₂*Et₂O / CH₂Cl₂ / 1 h / -20 °C

2: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

3: 1.) tris(triphenylphosphine)rhodium(I) chloride, catecholborane, 2.) 2M NaOH, 30percent aq. H₂O₂ / 1.) THF, 50 min, 2.) THF, EtOH, a) 0 deg C, 30 min, b) from 0 deg C to RT, 30 min

4: 89 percent / DMAP, pyridine / CH₂Cl₂

5: 1.) N-methylmorpholine N-oxide, OsO₄, 2.) NaIO₄ / 1.) t-BuOH, THF, H₂O, 20 h, 2.) t-BuOH, THF, H₂O, 20 h

6: 99 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

7: 80 percent / BF₃*Et₂O / CH₂Cl₂ / 8 h / -78 °C

With pyridine; 2,6-dimethylpyridine; dmap; sodium hydroxide; sodium periodate; Wilkinson's catalyst; osmium(VIII) oxide; boron trifluoride diethyl etherate; dihydrogen peroxide; 4-methylmorpholine N-oxide; triethylamine; magnesium bromide; benzo[1,3,2]dioxaborole; In dichloromethane;

DOI:10.1021/ja00050a024

Reference yield:

<4S,3(2S)>-4-benzyl-3-(2-hydroxy-3,3,4-trimethyl-4-pentenoyl)-2-oxazolidinone (139426-79-2) → <3R,4S,5S,9S,10R,11R>-9-hydroxy-3-methoxy-5-<(p-methoxybenzyl)oxy>-6,6,10-trimethyl-7-oxo-4,11-bis(triethylsiloxy)-12-tridecenyl pivalate (131698-92-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) AlMe₃ / 1.) CH₂Cl₂, toluene, 25 deg C, 30 min, 2.) CH₂Cl₂, toluene, reflux, 24 h

2: 1.) NaH / 1.) DMF, THF, 15 min, 2.) DMF, THF, 5 min

3: 93 percent / DIBAL-H / toluene / -78 °C

4: 71 percent / MgBr₂*Et₂O / CH₂Cl₂ / 1 h / -20 °C

5: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

6: 1.) tris(triphenylphosphine)rhodium(I) chloride, catecholborane, 2.) 2M NaOH, 30percent aq. H₂O₂ / 1.) THF, 50 min, 2.) THF, EtOH, a) 0 deg C, 30 min, b) from 0 deg C to RT, 30 min

7: 89 percent / DMAP, pyridine / CH₂Cl₂

8: 1.) N-methylmorpholine N-oxide, OsO₄, 2.) NaIO₄ / 1.) t-BuOH, THF, H₂O, 20 h, 2.) t-BuOH, THF, H₂O, 20 h

9: 99 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

10: 80 percent / BF₃*Et₂O / CH₂Cl₂ / 8 h / -78 °C

With pyridine; 2,6-dimethylpyridine; dmap; sodium hydroxide; sodium periodate; Wilkinson's catalyst; osmium(VIII) oxide; boron trifluoride diethyl etherate; dihydrogen peroxide; trimethylaluminum; sodium hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; magnesium bromide; benzo[1,3,2]dioxaborole; In dichloromethane; toluene;

DOI:10.1021/ja00050a024

upstream raw materials:

triethylsilyl chloride

3,3,4-trimethyl-4-pentenoic acid

triethylsilyl trifluoromethyl sulfonate

pivaloyl chloride

Downstream raw materials:

<2Z,4E,6E,8E,10S,11S,12R,13R,15R,15(2S,3S,5S,7R,8R,9S)>-15-<9-(tert-butyldimethylsiloxy)-7-(2-hydroxyethyl)-3--4,4,8-trimethyl-1,6-dioxaspiro<4.5>dec-2-yl>-11,13-bis(tert-butyldimethylsiloxy)-15-methoxy-3,7,8,10,12-pentam

<2Z,4E,6E,8E,10S,11S,12R,13R,15R,15(2S,3S,5S,7R,8R,9S)>-15-<9-(tert-butyldimethylsiloxy)-7-(2-oxoethyl)-3--4,4,8-trimethyl-1,6-dioxaspiro<4.5>dec-2-yl>-11,13-bis(tert-butyldimethylsiloxy)-15-methoxy-3,7,8,10,12-pentamethy

<2Z,4E,6E,8E,10S,11S,12R,13R,15R,15(2S,3S,5S,7R,8R,9S)>-15-<9-(tert-butyldimethylsiloxy)-7-<2-(tert-butyldimethylsiloxy)ethyl>-3--4,4,8-trimethyl-1,6-dioxaspiro<4.5>dec-2-yl>-11,13-bis(tert-butyldimethylsiloxy)-15-methoxy