(R)-3-(benzyloxy)-2-(2,2,6,6-tetramethylpiperidin-1-yloxy)propanal

Base Information

• Chemical Name: (R)-3-(benzyloxy)-2-(2,2,6,6-tetramethylpiperidin-1-yloxy)propanal
• CAS No.: 1583259-07-7
• Molecular Formula: C₁₉H₂₉NO₃
• Molecular Weight: 319.444
• Mol file: 1583259-07-7.mol

Synonyms:(R)-3-(benzyloxy)-2-(2,2,6,6-tetramethylpiperidin-1-yloxy)propanal

Chemical Property of (R)-3-(benzyloxy)-2-(2,2,6,6-tetramethylpiperidin-1-yloxy)propanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-(benzyloxy)-2-(2,2,6,6-tetramethylpiperidin-1-yloxy)propanal

There total 6 articles about (R)-3-(benzyloxy)-2-(2,2,6,6-tetramethylpiperidin-1-yloxy)propanal 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: 77.0%

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical (2564-83-2,45842-10-2,126517-51-9,25657-03-8,26933-82-4,54637-06-8,64104-42-3) + 3-Benzyloxypropanal (19790-60-4) → (R)-3-(benzyloxy)-2-(2,2,6,6-tetramethylpiperidin-1-yloxy)propanal (1583259-07-7)

Guidance literature:

With (R)-5-((1-Benzyl-1H-indol-3-yl)methyl)-2,2,3-trimethylimidazolin-4-one tetrafluoroboric acid; copper dichloride; In ethyl acetate; at -30 ℃; for 24h; Reagent/catalyst; Solvent; enantioselective reaction; Molecular sieve;

DOI:10.1021/ja502205q

Reference yield:

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical (2564-83-2,45842-10-2,126517-51-9,25657-03-8,26933-82-4,54637-06-8,64104-42-3) + 3-Benzyloxypropanal (19790-60-4) → (S)-3-(benzyloxy)-2-(2,2,6,6-tetramethylpiperidin-1-yloxy)propanal (1356648-26-4) + (R)-3-(benzyloxy)-2-(2,2,6,6-tetramethylpiperidin-1-yloxy)propanal (1583259-07-7)

Guidance literature:

With CHF₃O₃S*C₁₃H₁₈N₂O; copper dichloride; In diethyl ether; at -30 ℃; for 48h; Reagent/catalyst; Solvent; Overall yield = 68 %; enantioselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1021/ja502205q

Reference yield:

benzyl bromide (100-39-0) → (R)-3-(benzyloxy)-2-(2,2,6,6-tetramethylpiperidin-1-yloxy)propanal (1583259-07-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C

1.2: 16 h / 20 °C

2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 16 h / 20 °C

3.1: copper dichloride; (R)-5-((1-Benzyl-1H-indol-3-yl)methyl)-2,2,3-trimethylimidazolin-4-one tetrafluoroboric acid / ethyl acetate / 24 h / -30 °C / Molecular sieve

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; (R)-5-((1-Benzyl-1H-indol-3-yl)methyl)-2,2,3-trimethylimidazolin-4-one tetrafluoroboric acid; sodium hydride; copper dichloride; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/ja502205q

upstream raw materials:

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical

3-Benzyloxypropanal

benzyl bromide

3-benzyloxypropan-1-ol

Downstream raw materials:

5-benzyloxy-1-hydroxy-3-hydroxy-2-methoxy-β-D-ribose

5-benzyloxy-1-hydroxy-3-hydroxy-2-methoxy-α-D-ribose

5-benzyloxy-2-desoxy-3-hydroxy-D-lyxolactone

5-benzyloxy-2-desoxy-1-hydroxy-3-hydroxy-β-D-lyxose

Refernces