(2S/R,3S,7R)-8-tert-butyldiphenylsilyloxy-3,7-dimethyl-2-octanol

Base Information

• Chemical Name: (2S/R,3S,7R)-8-tert-butyldiphenylsilyloxy-3,7-dimethyl-2-octanol
• CAS No.: 250229-64-2
• Molecular Formula: C₂₆H₄₀O₂Si
• Molecular Weight: 412.688
• Mol file: 250229-64-2.mol

Synonyms:(2S/R,3S,7R)-8-tert-butyldiphenylsilyloxy-3,7-dimethyl-2-octanol

Chemical Property of (2S/R,3S,7R)-8-tert-butyldiphenylsilyloxy-3,7-dimethyl-2-octanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S/R,3S,7R)-8-tert-butyldiphenylsilyloxy-3,7-dimethyl-2-octanol

There total 6 articles about (2S/R,3S,7R)-8-tert-butyldiphenylsilyloxy-3,7-dimethyl-2-octanol 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: 88.0%

methylmagnesium bromide (75-16-1) + (2S,6R)-7-tert-butyldiphenylsilyloxy-2,6-dimethylheptanal (250229-63-1) → (2S/R,3S,7R)-8-tert-butyldiphenylsilyloxy-3,7-dimethyl-2-octanol (250229-64-2)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1002/(sici)1099-0690(199909)1999:9<2175::aid-ejoc2175>3.0.co;2-v

Reference yield:

2,6-dimethyl-1,7-heptanediol (40325-99-3) → (2S/R,3S,7R)-8-tert-butyldiphenylsilyloxy-3,7-dimethyl-2-octanol (250229-64-2)

Guidance literature:

Multi-step reaction with 5 steps

1: Lipase PS / tetrahydrofuran / 72 h / 0 °C

2: 96 percent / imidazole / dimethylformamide / 4 h / 20 °C

3: 99 percent / K₂CO₃ / methanol / 5 h / 20 °C

4: 95 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C

5: 88 percent / tetrahydrofuran / 1 h / -78 °C

With pyridine; 1H-imidazole; potassium carbonate; Dess-Martin periodane; Lipase PS; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Esterification / 2: Silylation / 3: Deacetylation / 4: Oxidation / 5: Methylation;

DOI:10.1002/(sici)1099-0690(199909)1999:9<2175::aid-ejoc2175>3.0.co;2-v

Reference yield:

(2S,6R)-7-tert-butyldiphenylsilyloxy-2,6-dimethyl-1-heptanol (101382-88-1) → (2S/R,3S,7R)-8-tert-butyldiphenylsilyloxy-3,7-dimethyl-2-octanol (250229-64-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / Dess-Martin periodinane / pyridine; CH₂Cl₂

2: 88 percent / tetrahydrofuran / 1 h / -78 °C

With Dess-Martin periodane; In tetrahydrofuran; pyridine; dichloromethane; 1: Oxidation / 2: Grignard reaction;

DOI:10.1002/1099-0690(200004)2000:7<1307::AID-EJOC1307>3.0.CO;2-X

upstream raw materials:

methylmagnesium bromide

(2S,6R)-7-tert-butyldiphenylsilyloxy-2,6-dimethylheptanal

(2S,6R)-7-tert-butyldiphenylsilyloxy-2,6-dimethyl-1-heptanol

tert-butylchlorodiphenylsilane

Downstream raw materials:

(2R,6S,7R/S)-2,6-dimethyl-7-tetrahydropyranyloxyoctyl tosylate

(2R,6S,7R/S)-1-tert-butyldiphenylsilyloxy-2,6-dimethyl-7-tetrahydropyranyloxyoctane

(2S,3S,7R)-8-tert-butyldiphenylsilyloxy-3,7-dimethyl-2-octanol