(2R,3S)-1-(tert-butyldiphenylsilyloxy)-3,7-dimethyl-6-octene-2,3-diol

Base Information

• Chemical Name: (2R,3S)-1-(tert-butyldiphenylsilyloxy)-3,7-dimethyl-6-octene-2,3-diol
• CAS No.: 1109222-01-6
• Molecular Formula: C₂₆H₃₈O₃Si
• Molecular Weight: 426.671
• Mol file: 1109222-01-6.mol

Synonyms:(2R,3S)-1-(tert-butyldiphenylsilyloxy)-3,7-dimethyl-6-octene-2,3-diol

Chemical Property of (2R,3S)-1-(tert-butyldiphenylsilyloxy)-3,7-dimethyl-6-octene-2,3-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-1-(tert-butyldiphenylsilyloxy)-3,7-dimethyl-6-octene-2,3-diol

There total 5 articles about (2R,3S)-1-(tert-butyldiphenylsilyloxy)-3,7-dimethyl-6-octene-2,3-diol 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: 95.0%

(2R,3S)-3,7-dimethyloct-6-ene-1,2,3-triol (121468-45-9) + tert-butylchlorodiphenylsilane (58479-61-1) → (2R,3S)-1-(tert-butyldiphenylsilyloxy)-3,7-dimethyl-6-octene-2,3-diol (1109222-01-6)

Guidance literature:

With 1H-imidazole; dmap; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.tetlet.2008.10.092

Reference yield:

3,7-dimethyl-6-octene-1,2,3-triol (65180-52-1) + tert-butylchlorodiphenylsilane (58479-61-1) → (2R,3S)-1-(tert-butyldiphenylsilyloxy)-3,7-dimethyl-6-octene-2,3-diol (1109222-01-6) + (2S,3R)-1-(tert-butyldiphenylsilyloxy)-3,7-dimethyl-6-octene-2,3-diol (1609197-51-4)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃; for 0.0833333h; Overall yield = 92 mg;

DOI:10.3762/bjoc.9.273

Reference yield:

6-Methyl-hept-5-en-2-on (110-93-0,129085-68-3) → (2R,3S)-1-(tert-butyldiphenylsilyloxy)-3,7-dimethyl-6-octene-2,3-diol (1109222-01-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

1.2: 1 h / -78 °C / Inert atmosphere

2.1: chloro-trimethyl-silane / methanol / 1 h / Inert atmosphere

3.1: lithium aluminium tetrahydride / diethyl ether / 0 - 20 °C / Inert atmosphere

4.1: triethylamine; dmap / dichloromethane / Inert atmosphere

With dmap; lithium aluminium tetrahydride; chloro-trimethyl-silane; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1016/j.bmcl.2015.06.083

upstream raw materials:

(2R,3S)-3,7-dimethyloct-6-ene-1,2,3-triol

tert-butylchlorodiphenylsilane

3,7-dimethyl-6-octene-1,2,3-triol

6-Methyl-hept-5-en-2-on

Downstream raw materials:

(S)-1-tert-butyldiphenylsilyloxy-3-hydroxy-3,7-dimethyl-6-octen-2-one