(S)-4-Benzyl-3-((1S,2S,3R)-2-benzyloxy-1-hydroxy-3-phenyl-3-triisopropylsilanyloxy-propyl)-5,5-dimethyl-oxazolidin-2-one

Base Information

• Chemical Name: (S)-4-Benzyl-3-((1S,2S,3R)-2-benzyloxy-1-hydroxy-3-phenyl-3-triisopropylsilanyloxy-propyl)-5,5-dimethyl-oxazolidin-2-one
• CAS No.: 768391-75-9
• Molecular Formula: C₃₇H₅₁NO₅Si
• Molecular Weight: 617.901

Synonyms:(S)-4-Benzyl-3-((1S,2S,3R)-2-benzyloxy-1-hydroxy-3-phenyl-3-triisopropylsilanyloxy-propyl)-5,5-dimethyl-oxazolidin-2-one

Chemical Property of (S)-4-Benzyl-3-((1S,2S,3R)-2-benzyloxy-1-hydroxy-3-phenyl-3-triisopropylsilanyloxy-propyl)-5,5-dimethyl-oxazolidin-2-one

Chemical Property:

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Technology Process of (S)-4-Benzyl-3-((1S,2S,3R)-2-benzyloxy-1-hydroxy-3-phenyl-3-triisopropylsilanyloxy-propyl)-5,5-dimethyl-oxazolidin-2-one

There total 2 articles about (S)-4-Benzyl-3-((1S,2S,3R)-2-benzyloxy-1-hydroxy-3-phenyl-3-triisopropylsilanyloxy-propyl)-5,5-dimethyl-oxazolidin-2-one 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: 64.0%

(2'S,3'R,4S)-4-benzyl-3-(2'-benzyloxy-3'-(triisopropylsilanyloxy)-3'-phenylpropionyl)-5,5-dimethyloxazolidin-2-one (768391-71-5) → (S)-4-Benzyl-3-((1S,2S,3R)-2-benzyloxy-1-hydroxy-3-phenyl-3-triisopropylsilanyloxy-propyl)-5,5-dimethyl-oxazolidin-2-one (768391-75-9)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 0.333333h;

DOI:10.1016/j.tet.2004.05.123

Reference yield:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → (S)-4-Benzyl-3-((1S,2S,3R)-2-benzyloxy-1-hydroxy-3-phenyl-3-triisopropylsilanyloxy-propyl)-5,5-dimethyl-oxazolidin-2-one (768391-75-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / DMAP / CH₂Cl₂ / 18 h / 0 °C

2: 64 percent / DIBAL / CH₂Cl₂ / 0.33 h / -78 °C

With dmap; diisobutylaluminium hydride; In dichloromethane;

DOI:10.1016/j.tet.2004.05.123

Reference yield: 91.0%

(S)-4-Benzyl-3-((1S,2S,3R)-2-benzyloxy-1-hydroxy-3-phenyl-3-triisopropylsilanyloxy-propyl)-5,5-dimethyl-oxazolidin-2-one (768391-75-9) → (2S,3R)-2-benzyloxy-3-(triisopropylsilanyloxy)-3-phenylpropionaldehyde

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 0.25h;

DOI:10.1016/j.tet.2004.05.123

upstream raw materials:

(2'S,3'R,4S)-4-benzyl-3-(2'-benzyloxy-3'-(triisopropylsilanyloxy)-3'-phenylpropionyl)-5,5-dimethyloxazolidin-2-one

triisopropylsilyl trifluoromethanesulfonate

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