(3R,4S,5R)-3,4-Bis<(tert-butyldimethylsilyl)oxy>-5-(2-hydroxyethyl)-1-benzyl-2-pyrrolinone

Base Information

• Chemical Name: (3R,4S,5R)-3,4-Bis<(tert-butyldimethylsilyl)oxy>-5-(2-hydroxyethyl)-1-benzyl-2-pyrrolinone
• CAS No.: 163002-05-9
• Molecular Formula: C₂₅H₄₅NO₄Si₂
• Molecular Weight: 479.808

Synonyms:(3R,4S,5R)-3,4-Bis<(tert-butyldimethylsilyl)oxy>-5-(2-hydroxyethyl)-1-benzyl-2-pyrrolinone

Chemical Property of (3R,4S,5R)-3,4-Bis<(tert-butyldimethylsilyl)oxy>-5-(2-hydroxyethyl)-1-benzyl-2-pyrrolinone

Chemical Property:

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Technology Process of (3R,4S,5R)-3,4-Bis<(tert-butyldimethylsilyl)oxy>-5-(2-hydroxyethyl)-1-benzyl-2-pyrrolinone

There total 2 articles about (3R,4S,5R)-3,4-Bis<(tert-butyldimethylsilyl)oxy>-5-(2-hydroxyethyl)-1-benzyl-2-pyrrolinone 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:

[(2R,3S,4R)-1-Benzyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-oxo-pyrrolidin-2-yl]-acetaldehyde (1053256-85-1) → (3R,4S,5R)-3,4-Bis<(tert-butyldimethylsilyl)oxy>-5-(2-hydroxyethyl)-1-benzyl-2-pyrrolinone (163002-05-9)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 2h; Yield given;

DOI:10.1021/jo00106a021

Reference yield:

(3R,4S)-3,4-Bis<(tert-butyldimethylsilyl)oxy>-5-allyl-1-benzyl-2-pyrrolidinone → (3R,4S,5R)-3,4-Bis<(tert-butyldimethylsilyl)oxy>-5-(2-hydroxyethyl)-1-benzyl-2-pyrrolinone (163002-05-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) O₃, O₂, 2.) Me₂S / 1.) MeOH, -78 deg C, 1 h, 2.) overnight

2: NaBH₄ / methanol / 2 h / 0 °C

With sodium tetrahydroborate; dimethylsulfide; oxygen; ozone; In methanol;

DOI:10.1021/jo00106a021

Reference yield:

(3R,4S,5R)-3,4-Bis<(tert-butyldimethylsilyl)oxy>-5-(2-hydroxyethyl)-1-benzyl-2-pyrrolinone (163002-05-9) → 2-[(2R,3S,4S)-1-Benzyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-pyrrolidin-2-yl]-ethanol

Guidance literature:

With dimethylsulfide borane complex; In tetrahydrofuran; at 0 ℃; for 24h;

DOI:10.1021/jo00106a021

upstream raw materials:

[(2R,3S,4R)-1-Benzyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-oxo-pyrrolidin-2-yl]-acetaldehyde

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