(2S,3R,5S)-2-Hexyl-3-hydroxy-5-triisopropylsilanyloxy-decanoic acid benzyl ester

Base Information

• Chemical Name: (2S,3R,5S)-2-Hexyl-3-hydroxy-5-triisopropylsilanyloxy-decanoic acid benzyl ester
• CAS No.: 907217-50-9
• Molecular Formula: C₃₂H₅₈O₄Si
• Molecular Weight: 534.896
• Mol file: 907217-50-9.mol

Synonyms:(2S,3R,5S)-2-Hexyl-3-hydroxy-5-triisopropylsilanyloxy-decanoic acid benzyl ester

Chemical Property of (2S,3R,5S)-2-Hexyl-3-hydroxy-5-triisopropylsilanyloxy-decanoic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,5S)-2-Hexyl-3-hydroxy-5-triisopropylsilanyloxy-decanoic acid benzyl ester

There total 7 articles about (2S,3R,5S)-2-Hexyl-3-hydroxy-5-triisopropylsilanyloxy-decanoic acid benzyl ester 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: 97.0%

(2S,3R,5S)-2-Hexyl-3,5-dihydroxy-decanoic acid benzyl ester (907217-49-6) + triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → (2S,3R,5S)-2-Hexyl-3-hydroxy-5-triisopropylsilanyloxy-decanoic acid benzyl ester (907217-50-9)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/jo060844m

Reference yield:

1-((S)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-octan-1-one (907217-45-2) → (2S,3R,5S)-2-Hexyl-3-hydroxy-5-triisopropylsilanyloxy-decanoic acid benzyl ester (907217-50-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 78 percent / TMEDA / CH₂Cl₂ / 2 h / 0 °C

2: 75 percent / DMAP / CH₂Cl₂ / 46 h / 20 °C

3: 87 percent / NaHCO₃; I₂ / acetone; H₂O / 15 h / 0 °C

4: 97 percent / Me₄NBH(OAc)3 / acetonitrile; acetic acid / 3 h / -15 °C

5: 97 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

With 2,6-dimethylpyridine; dmap; N,N,N,N,-tetramethylethylenediamine; iodine; sodium hydrogencarbonate; tetramethylammonium triacetoxyborohydride; In dichloromethane; water; acetic acid; acetone; acetonitrile;

DOI:10.1021/jo060844m

Reference yield:

(2S,3R)-2-Hexyl-3-hydroxy-5-oxo-decanoic acid benzyl ester (907217-48-5) → (2S,3R,5S)-2-Hexyl-3-hydroxy-5-triisopropylsilanyloxy-decanoic acid benzyl ester (907217-50-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / Me₄NBH(OAc)3 / acetonitrile; acetic acid / 3 h / -15 °C

2: 97 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

With 2,6-dimethylpyridine; tetramethylammonium triacetoxyborohydride; In dichloromethane; acetic acid; acetonitrile;

DOI:10.1021/jo060844m

upstream raw materials:

(2S,3R,5S)-2-Hexyl-3,5-dihydroxy-decanoic acid benzyl ester

triisopropylsilyl trifluoromethanesulfonate

1-((S)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-octan-1-one

(2S,3R)-2-Hexyl-3-hydroxy-5-oxo-decanoic acid benzyl ester

Downstream raw materials:

valilactone

(2S,3R,5S)-2-Hexyl-3-methanesulfonyloxy-5-triisopropylsilanyloxy-decanoic acid benzyl ester