(3R,4S,5S)-3-Methoxy-5-(4-methoxy-benzyloxy)-6,6,7-trimethyl-4-triethylsilanyloxy-oct-7-enal

Base Information

• Chemical Name: (3R,4S,5S)-3-Methoxy-5-(4-methoxy-benzyloxy)-6,6,7-trimethyl-4-triethylsilanyloxy-oct-7-enal
• CAS No.: 144467-85-6
• Molecular Formula: C₂₆H₄₄O₅Si
• Molecular Weight: 464.718
• Mol file: 144467-85-6.mol

Synonyms:(3R,4S,5S)-3-Methoxy-5-(4-methoxy-benzyloxy)-6,6,7-trimethyl-4-triethylsilanyloxy-oct-7-enal

Chemical Property of (3R,4S,5S)-3-Methoxy-5-(4-methoxy-benzyloxy)-6,6,7-trimethyl-4-triethylsilanyloxy-oct-7-enal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S,5S)-3-Methoxy-5-(4-methoxy-benzyloxy)-6,6,7-trimethyl-4-triethylsilanyloxy-oct-7-enal

There total 11 articles about (3R,4S,5S)-3-Methoxy-5-(4-methoxy-benzyloxy)-6,6,7-trimethyl-4-triethylsilanyloxy-oct-7-enal 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:

3,3,4-trimethyl-4-pentenoic acid (90370-81-3) → (3R,4S,5S)-3-Methoxy-5-(4-methoxy-benzyloxy)-6,6,7-trimethyl-4-triethylsilanyloxy-oct-7-enal (144467-85-6)

Guidance literature:

Multi-step reaction with 9 steps

1: Et₃N / diethyl ether / 1 h / 0 °C

2: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, a) -78 deg C, 15 min, b) 0 deg C, 30 min

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

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

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

6: 93 percent / DIBAL-H / toluene / -78 °C

7: 71 percent / MgBr₂*Et₂O / CH₂Cl₂ / 1 h / -20 °C

8: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

9: 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

With 2,6-dimethylpyridine; sodium hydroxide; Wilkinson's catalyst; n-butyllithium; dihydrogen peroxide; trimethylaluminum; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; N-(benzenesulfonyl)-3-phenyloxaziridine; triethylamine; magnesium bromide; benzo[1,3,2]dioxaborole; In diethyl ether; dichloromethane; toluene;

DOI:10.1021/ja00050a024

Reference yield:

triethylsilyl trifluoromethyl sulfonate (79271-56-0) → (3R,4S,5S)-3-Methoxy-5-(4-methoxy-benzyloxy)-6,6,7-trimethyl-4-triethylsilanyloxy-oct-7-enal (144467-85-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

2: 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

With 2,6-dimethylpyridine; sodium hydroxide; Wilkinson's catalyst; dihydrogen peroxide; benzo[1,3,2]dioxaborole; In dichloromethane;

DOI:10.1021/ja00050a024

Reference yield:

p-Methoxybenzyl bromide (2746-25-0) → (3R,4S,5S)-3-Methoxy-5-(4-methoxy-benzyloxy)-6,6,7-trimethyl-4-triethylsilanyloxy-oct-7-enal (144467-85-6)

Guidance literature:

Multi-step reaction with 5 steps

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

2: 93 percent / DIBAL-H / toluene / -78 °C

3: 71 percent / MgBr₂*Et₂O / CH₂Cl₂ / 1 h / -20 °C

4: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

5: 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

With 2,6-dimethylpyridine; sodium hydroxide; Wilkinson's catalyst; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; magnesium bromide; benzo[1,3,2]dioxaborole; In dichloromethane; toluene;

DOI:10.1021/ja00050a024

upstream raw materials:

Triethyl-[(1S,2S)-1-((R)-1-methoxy-allyl)-2-(4-methoxy-benzyloxy)-3,3,4-trimethyl-pent-4-enyloxy]-silane

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

triethylsilyl trifluoromethyl sulfonate

p-Methoxybenzyl bromide

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-(tert-butyldimethylsiloxy)ethyl>-3--4,4,8-trimethyl-1,6-dioxaspiro<4.5>dec-2-yl>-11,13-bis(tert-butyldimethylsiloxy)-15-methoxy

<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-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