<3R,4S,5S>-3-methoxy-5-<(p-methoxybenzyl)oxy>-6,6-dimethyl-4-(triethylsiloxy)-7-(trimethylsiloxy)-7-octenyl pivalate

Base Information

• Chemical Name: <3R,4S,5S>-3-methoxy-5-<(p-methoxybenzyl)oxy>-6,6-dimethyl-4-(triethylsiloxy)-7-(trimethylsiloxy)-7-octenyl pivalate
• CAS No.: 131698-91-4
• Molecular Formula: C₃₃H₆₀O₇Si₂
• Molecular Weight: 625.006
• Mol file: 131698-91-4.mol

Synonyms:<3R,4S,5S>-3-methoxy-5-<(p-methoxybenzyl)oxy>-6,6-dimethyl-4-(triethylsiloxy)-7-(trimethylsiloxy)-7-octenyl pivalate

Chemical Property of <3R,4S,5S>-3-methoxy-5-<(p-methoxybenzyl)oxy>-6,6-dimethyl-4-(triethylsiloxy)-7-(trimethylsiloxy)-7-octenyl pivalate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <3R,4S,5S>-3-methoxy-5-<(p-methoxybenzyl)oxy>-6,6-dimethyl-4-(triethylsiloxy)-7-(trimethylsiloxy)-7-octenyl pivalate

There total 16 articles about <3R,4S,5S>-3-methoxy-5-<(p-methoxybenzyl)oxy>-6,6-dimethyl-4-(triethylsiloxy)-7-(trimethylsiloxy)-7-octenyl 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: 99.0%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + <3R,4S,5S>-3-methoxy-5-<(p-methoxybenzyl)oxy>-6,6-dimethyl-7-oxo-4-(triethylsiloxy)octyl pivalate (139426-85-0) → <3R,4S,5S>-3-methoxy-5-<(p-methoxybenzyl)oxy>-6,6-dimethyl-4-(triethylsiloxy)-7-(trimethylsiloxy)-7-octenyl pivalate (131698-91-4)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1021/ja00050a024

Reference yield:

(S)-2-(4-Methoxy-benzyloxy)-3,3,4-trimethyl-pent-4-enal (139426-80-5) → <3R,4S,5S>-3-methoxy-5-<(p-methoxybenzyl)oxy>-6,6-dimethyl-4-(triethylsiloxy)-7-(trimethylsiloxy)-7-octenyl pivalate (131698-91-4)

Guidance literature:

Multi-step reaction with 6 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

With pyridine; 2,6-dimethylpyridine; dmap; sodium hydroxide; sodium periodate; Wilkinson's catalyst; osmium(VIII) oxide; 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>-3-methoxy-5-<(p-methoxybenzyl)oxy>-6,6-dimethyl-4-(triethylsiloxy)-7-(trimethylsiloxy)-7-octenyl pivalate (131698-91-4)

Guidance literature:

Multi-step reaction with 9 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

With pyridine; 2,6-dimethylpyridine; dmap; sodium hydroxide; sodium periodate; Wilkinson's catalyst; osmium(VIII) oxide; 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:

trimethylsilyl trifluoromethanesulfonate

<3R,4S,5S>-3-methoxy-5-<(p-methoxybenzyl)oxy>-6,6-dimethyl-7-oxo-4-(triethylsiloxy)octyl pivalate

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

triethylsilyl trifluoromethyl sulfonate

Downstream raw materials:

<3R,3(2S,3S,5S,7R,8R,9S)>-3-<9-hydroxy-3-<(p-methoxybenzyl)oxy>-4,4,8-trimethyl-7-vinyl-1,6-dioxaspiro<4.5>dec-2-yl>-3-methoxypropyl pivalate

<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