(2R,4S,5S,6S)-(+)-7-t-butyldiphenylsilyloxy-5-ethyl-2,4-dimethylheptane-1,5-diol

Base Information

• Chemical Name: (2R,4S,5S,6S)-(+)-7-t-butyldiphenylsilyloxy-5-ethyl-2,4-dimethylheptane-1,5-diol
• CAS No.: 130808-32-1
• Molecular Formula: C₂₇H₄₂O₃Si
• Molecular Weight: 442.714
• Mol file: 130808-32-1.mol

Synonyms:(2R,4S,5S,6S)-(+)-7-t-butyldiphenylsilyloxy-5-ethyl-2,4-dimethylheptane-1,5-diol

Chemical Property of (2R,4S,5S,6S)-(+)-7-t-butyldiphenylsilyloxy-5-ethyl-2,4-dimethylheptane-1,5-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4S,5S,6S)-(+)-7-t-butyldiphenylsilyloxy-5-ethyl-2,4-dimethylheptane-1,5-diol

There total 10 articles about (2R,4S,5S,6S)-(+)-7-t-butyldiphenylsilyloxy-5-ethyl-2,4-dimethylheptane-1,5-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: 76.0%

C36H64O3Si3 (130514-53-3) → (2R,4S,5S,6S)-(+)-7-t-butyldiphenylsilyloxy-5-ethyl-2,4-dimethylheptane-1,5-diol (130808-32-1)

Guidance literature:

With pyridinium p-toluenesulfonate; In ethanol; for 15h; Ambient temperature;

Reference yield:

(S)-(-)-2,4-dimethylpent-4-en-1-ol (82507-47-9) → (2R,4S,5S,6S)-(+)-7-t-butyldiphenylsilyloxy-5-ethyl-2,4-dimethylheptane-1,5-diol (130808-32-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 64 percent / triethylamine, pyridine-sulfur trioxide complex / dimethylsulfoxide / 3 h / 25 °C

2: 1.) 9-borabicyclo<3.3.1>non-9-yl trifluoromethanesulfonate, diisopropylethylamine / 1.) dichloromethane, 0 deg C, 0.5 h, 2a.) -78 deg C, 0.5 h, 2b.) RT, 1.5 h

3: 85 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 15 h / 25 °C

4: 1.) C₆H₁₃BH₂ (from borane-tetrahydrofuran and 2,3-dimethylbut-2-ene), 2.) aq. sodium bicarbonate, 30percent H₂O₂ / 1.) THF, 0 deg C, 5 h, 2.) 25 deg C, 12 h

5: 94 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

6: 71 percent / lithium borohydride / tetrahydrofuran / 15 h / 25 °C

7: 82 percent / imidazole / dimethylformamide / 5 h / Ambient temperature

8: 76 percent / pyridinium p-toluenesulfonate / ethanol / 15 h / Ambient temperature

With 1H-imidazole; 2,6-dimethylpyridine; dmap; lithium borohydride; C₆H₁₃BH₂ (from borane-tetrahydrofuran and 2,3-dimethylbut-2-ene); dihydrogen peroxide; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 9-BBN triflate; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

Reference yield:

(S)-(+)-2,4-dimethylpent-4-enal (82507-48-0) → (2R,4S,5S,6S)-(+)-7-t-butyldiphenylsilyloxy-5-ethyl-2,4-dimethylheptane-1,5-diol (130808-32-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) 9-borabicyclo<3.3.1>non-9-yl trifluoromethanesulfonate, diisopropylethylamine / 1.) dichloromethane, 0 deg C, 0.5 h, 2a.) -78 deg C, 0.5 h, 2b.) RT, 1.5 h

2: 85 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 15 h / 25 °C

3: 1.) C₆H₁₃BH₂ (from borane-tetrahydrofuran and 2,3-dimethylbut-2-ene), 2.) aq. sodium bicarbonate, 30percent H₂O₂ / 1.) THF, 0 deg C, 5 h, 2.) 25 deg C, 12 h

4: 94 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

5: 71 percent / lithium borohydride / tetrahydrofuran / 15 h / 25 °C

6: 82 percent / imidazole / dimethylformamide / 5 h / Ambient temperature

7: 76 percent / pyridinium p-toluenesulfonate / ethanol / 15 h / Ambient temperature

With 1H-imidazole; 2,6-dimethylpyridine; dmap; lithium borohydride; C₆H₁₃BH₂ (from borane-tetrahydrofuran and 2,3-dimethylbut-2-ene); dihydrogen peroxide; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; 9-BBN triflate; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

C₃₆H₆₄O₃Si₃

(S)-(+)-2,4-dimethylpent-4-enal

(S)-(-)-2,4-dimethylpent-4-en-1-ol

(2S,3S,4S,6R)-(-)-7-t-butyldimethylsilyloxy-2-ethyl-4,6-dimethyl-3-trimethylsilyloxyheptan-1-ol

Downstream raw materials:

(1'S,3R,5S,6S)-(+)-6-<1'-(t-butyldiphenylsilyloxymethyl)propyl>-3,5-dimethyltetrahydropyran-2-one