(S)-tert-butyl 4-((R)-1-(benzyloxy)-4-hydroxybut-2-yn-1-yl)-2,2-dimethyloxazolidine-3-carboxylate

Base Information

• Chemical Name: (S)-tert-butyl 4-((R)-1-(benzyloxy)-4-hydroxybut-2-yn-1-yl)-2,2-dimethyloxazolidine-3-carboxylate
• CAS No.: 1274699-53-4
• Molecular Formula: C₂₁H₂₉NO₅
• Molecular Weight: 375.465
• Mol file: 1274699-53-4.mol

Synonyms:(S)-tert-butyl 4-((R)-1-(benzyloxy)-4-hydroxybut-2-yn-1-yl)-2,2-dimethyloxazolidine-3-carboxylate

Chemical Property of (S)-tert-butyl 4-((R)-1-(benzyloxy)-4-hydroxybut-2-yn-1-yl)-2,2-dimethyloxazolidine-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-tert-butyl 4-((R)-1-(benzyloxy)-4-hydroxybut-2-yn-1-yl)-2,2-dimethyloxazolidine-3-carboxylate

There total 3 articles about (S)-tert-butyl 4-((R)-1-(benzyloxy)-4-hydroxybut-2-yn-1-yl)-2,2-dimethyloxazolidine-3-carboxylate 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:

C27H43NO5Si (1274699-54-5) → (S)-tert-butyl 4-((R)-1-(benzyloxy)-4-hydroxybut-2-yn-1-yl)-2,2-dimethyloxazolidine-3-carboxylate (1274699-53-4)

Guidance literature:

With ammonium fluoride-hydrogen fluoride; In methanol; at 20 ℃; for 18h;

DOI:10.1039/c0ob00747a

Reference yield:

(S)-tert-butyl 4-((R)-4-((tert-butyldimethylsilyl)oxy)-1-hydroxybut-2-yn-1-yl)-2,2-dimethyloxazolidine-3-carboxylate → (S)-tert-butyl 4-((R)-1-(benzyloxy)-4-hydroxybut-2-yn-1-yl)-2,2-dimethyloxazolidine-3-carboxylate (1274699-53-4)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride; potassium iodide / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 0 °C

2: ammonium fluoride-hydrogen fluoride / methanol / 18 h / 20 °C

With ammonium fluoride-hydrogen fluoride; sodium hydride; potassium iodide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; mineral oil;

DOI:10.1039/c0ob00747a

Reference yield:

(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (102308-32-7) → (S)-tert-butyl 4-((R)-1-(benzyloxy)-4-hydroxybut-2-yn-1-yl)-2,2-dimethyloxazolidine-3-carboxylate (1274699-53-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1.17 h / -78 °C / Inert atmosphere

1.2: 2 h / -78 °C / Inert atmosphere

2.1: sodium hydride; potassium iodide / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C / Inert atmosphere

3.1: ammonium fluoride-hydrogen fluoride / methanol / 18 h / 20 °C

With n-butyllithium; ammonium fluoride-hydrogen fluoride; sodium hydride; potassium iodide; In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1016/j.tet.2014.02.020

upstream raw materials:

C₂₇H₄₃NO₅Si

(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Downstream raw materials:

(2S,3S,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-ium chloride

(S)-tert-butyl 4-((1S,2R,3S)-1-(benzyloxy)-2,3-dihydroxy-4-(tosyloxy)butyl)-2,2-dimethyloxazolidine-3-carboxylate

C₂₀H₂₇NO₇S

(3S,4R,5S,6S)-5-(benzyloxy)-6-(hydroxymethyl)piperidine-3,4-diol