(2S,3R,4R)-1-benzyl-4-benzyloxy-2-(2-tert-butyldimethylsilyloxyethyl)pyrrolidin-3-ol

Base Information

• Chemical Name: (2S,3R,4R)-1-benzyl-4-benzyloxy-2-(2-tert-butyldimethylsilyloxyethyl)pyrrolidin-3-ol
• CAS No.: 893402-99-8
• Molecular Formula: C₂₆H₃₉NO₃Si
• Molecular Weight: 441.686

Synonyms:(2S,3R,4R)-1-benzyl-4-benzyloxy-2-(2-tert-butyldimethylsilyloxyethyl)pyrrolidin-3-ol

Chemical Property of (2S,3R,4R)-1-benzyl-4-benzyloxy-2-(2-tert-butyldimethylsilyloxyethyl)pyrrolidin-3-ol

Chemical Property:

Purity/Quality:

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Technology Process of (2S,3R,4R)-1-benzyl-4-benzyloxy-2-(2-tert-butyldimethylsilyloxyethyl)pyrrolidin-3-ol

There total 2 articles about (2S,3R,4R)-1-benzyl-4-benzyloxy-2-(2-tert-butyldimethylsilyloxyethyl)pyrrolidin-3-ol 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%

tert-butyldimethylsilyl chloride (18162-48-6) + (2S,3R,4R)-1-benzyl-4-benzyloxy-2-(2-hydroxyethyl)pyrrolidin-3-ol (800407-09-4) → (2S,3R,4R)-1-benzyl-4-benzyloxy-2-(2-tert-butyldimethylsilyloxyethyl)pyrrolidin-3-ol (893402-99-8)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 25 ℃; for 3h;

DOI:10.1016/j.tet.2006.02.074

Reference yield:

(3aS,6R,6aR)-4-Benzyl-6-benzyloxy-hexahydro-furo[3,2-b]pyrrol-2-one (800407-08-3) → (2S,3R,4R)-1-benzyl-4-benzyloxy-2-(2-tert-butyldimethylsilyloxyethyl)pyrrolidin-3-ol (893402-99-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 25 °C

2: 95 percent / imidazole / CH₂Cl₂ / 3 h / 25 °C

With 1H-imidazole; lithium aluminium tetrahydride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2006.02.074

Reference yield: 82.0%

(2S,3R,4R)-1-benzyl-4-benzyloxy-2-(2-tert-butyldimethylsilyloxyethyl)pyrrolidin-3-ol (893402-99-8) + benzyl bromide (100-39-0) → (2S,3R,4R)-1-benzyl-3,4-bis(benzyloxy)-2-(2-tert-butyldimethylsilyloxyethyl)pyrrolidin-3-ol (893403-01-5)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 25 ℃; for 5h;

DOI:10.1016/j.tet.2006.02.074

upstream raw materials:

tert-butyldimethylsilyl chloride

(2S,3R,4R)-1-benzyl-4-benzyloxy-2-(2-hydroxyethyl)pyrrolidin-3-ol

(3aS,6R,6aR)-4-Benzyl-6-benzyloxy-hexahydro-furo[3,2-b]pyrrol-2-one

Downstream raw materials:

(2S,3R,4R)-1-benzyl-3,4-bis(benzyloxy)-2-(2-tert-butyldimethylsilyloxyethyl)pyrrolidin-3-ol

(1R,2R,8aS)-octahydroindolizine-1,2-diol

((2S,3R,4R)-1-Benzyl-3,4-bis-benzyloxy-pyrrolidin-2-yl)-acetaldehyde

2-((2S,3R,4R)-1-benzyl-3,4-bis(benzyloxy)pyrrolidin-2-yl)ethanol

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