(8R,6R,5S,4S,3R)-9-(Benzyloxy)-8-methyl-6-(2-hydroxyethyl)-5-<(trimethylsilyl)oxy>-4-methoxy-1,3-bis<(tert-butyldimethylsilyl)oxy>nonane

Base Information

• Chemical Name: (8R,6R,5S,4S,3R)-9-(Benzyloxy)-8-methyl-6-(2-hydroxyethyl)-5-<(trimethylsilyl)oxy>-4-methoxy-1,3-bis<(tert-butyldimethylsilyl)oxy>nonane
• CAS No.: 157717-83-4
• Molecular Formula: C₃₅H₇₀O₆Si₃
• Molecular Weight: 671.194
• Mol file: 157717-83-4.mol

Synonyms:(8R,6R,5S,4S,3R)-9-(Benzyloxy)-8-methyl-6-(2-hydroxyethyl)-5-<(trimethylsilyl)oxy>-4-methoxy-1,3-bis<(tert-butyldimethylsilyl)oxy>nonane

Chemical Property of (8R,6R,5S,4S,3R)-9-(Benzyloxy)-8-methyl-6-(2-hydroxyethyl)-5-<(trimethylsilyl)oxy>-4-methoxy-1,3-bis<(tert-butyldimethylsilyl)oxy>nonane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (8R,6R,5S,4S,3R)-9-(Benzyloxy)-8-methyl-6-(2-hydroxyethyl)-5-<(trimethylsilyl)oxy>-4-methoxy-1,3-bis<(tert-butyldimethylsilyl)oxy>nonane

There total 16 articles about (8R,6R,5S,4S,3R)-9-(Benzyloxy)-8-methyl-6-(2-hydroxyethyl)-5-<(trimethylsilyl)oxy>-4-methoxy-1,3-bis<(tert-butyldimethylsilyl)oxy>nonane 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:

[(2R,4R,5S,6S,7R)-7,9-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-2-methyl-5-trimethylsilanyloxy-4-(2-trimethylsilanyloxy-ethyl)-nonyloxymethyl]-benzene (1053624-82-0) → (8R,6R,5S,4S,3R)-9-(Benzyloxy)-8-methyl-6-(2-hydroxyethyl)-5-<(trimethylsilyl)oxy>-4-methoxy-1,3-bis<(tert-butyldimethylsilyl)oxy>nonane (157717-83-4)

Guidance literature:

With potassium carbonate; In methanol; at 0 ℃; for 2h; Yield given;

DOI:10.1021/jo00090a032

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (8R,6R,5S,4S,3R)-9-(Benzyloxy)-8-methyl-6-(2-hydroxyethyl)-5-<(trimethylsilyl)oxy>-4-methoxy-1,3-bis<(tert-butyldimethylsilyl)oxy>nonane (157717-83-4)

Guidance literature:

Multi-step reaction with 10 steps

1: imidazole

2: OsO₄, Pb(OAc)4

3: 95 percent / n-Bu₂BOTf, i-Pr₂NEt / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) -78 deg C to r.t., 5 h

4: AlMe₃ / toluene / 1.) 0 deg C - r.t., 1 h, 2.) 0 deg C - r.t., overnight

5: imidazole / dimethylformamide

6: 87 percent / DIBAL-H / toluene / 0.17 h / -78 °C

7: 1.) Bu₃SnH, AIBN, 2.) MgBr₂*OEt₂ / 1.) toluene, 90 deg C, 2 h, 2.) CH₂Cl₂, 0 deg C, 1 h; -23 deg C to r.t., 5 h

8: 1.) 9-BBN, 2.) H₂O₂ / 1.) THF, sonicate, 90 min

9: DMAP / CH₂Cl₂ / 24 h

10: K₂CO₃ / methanol / 2 h / 0 °C

With 1H-imidazole; lead(IV) acetate; dmap; osmium(VIII) oxide; 9-borabicyclo[3.3.1]nonane dimer; 2,2'-azobis(isobutyronitrile); di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; trimethylaluminum; tri-n-butyl-tin hydride; diisobutylaluminium hydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; magnesium bromide; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00090a032

Reference yield:

1-[((S)-3-iodo-2-methylpropoxy)methyl]benzene (72297-80-4) → (8R,6R,5S,4S,3R)-9-(Benzyloxy)-8-methyl-6-(2-hydroxyethyl)-5-<(trimethylsilyl)oxy>-4-methoxy-1,3-bis<(tert-butyldimethylsilyl)oxy>nonane (157717-83-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / n-BuLi, TMEDA / tetrahydrofuran; hexane / 1.) 30 min, 2.) 1 h

2: 1.) Bu₃SnH, AIBN, 2.) MgBr₂*OEt₂ / 1.) toluene, 90 deg C, 2 h, 2.) CH₂Cl₂, 0 deg C, 1 h; -23 deg C to r.t., 5 h

3: 1.) 9-BBN, 2.) H₂O₂ / 1.) THF, sonicate, 90 min

4: DMAP / CH₂Cl₂ / 24 h

5: K₂CO₃ / methanol / 2 h / 0 °C

With dmap; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; 2,2'-azobis(isobutyronitrile); N,N,N,N,-tetramethylethylenediamine; dihydrogen peroxide; tri-n-butyl-tin hydride; potassium carbonate; magnesium bromide; In tetrahydrofuran; methanol; hexane; dichloromethane;

DOI:10.1021/jo00090a032

upstream raw materials:

[(2R,4R,5S,6S,7R)-7,9-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-2-methyl-5-trimethylsilanyloxy-4-(2-trimethylsilanyloxy-ethyl)-nonyloxymethyl]-benzene

1-[((S)-3-iodo-2-methylpropoxy)methyl]benzene

(R)-3-(benzyloxy)-2-methylpropan-1-ol

O-benzyl 2,2,2-trichloroacetimidate