(R)-2,3-diO-dibenzylglyceraldehyde (S)-α-methylbenzylimine

Base Information

• Chemical Name: (R)-2,3-diO-dibenzylglyceraldehyde (S)-α-methylbenzylimine
• CAS No.: 238401-88-2
• Molecular Formula: C₂₅H₂₇NO₂
• Molecular Weight: 373.495
• Mol file: 238401-88-2.mol

Synonyms:(R)-2,3-diO-dibenzylglyceraldehyde (S)-α-methylbenzylimine

Chemical Property of (R)-2,3-diO-dibenzylglyceraldehyde (S)-α-methylbenzylimine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2,3-diO-dibenzylglyceraldehyde (S)-α-methylbenzylimine

There total 1 articles about (R)-2,3-diO-dibenzylglyceraldehyde (S)-α-methylbenzylimine 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:

(S)-1-phenyl-ethylamine (2627-86-3) + (+)-(R)-2,3-bis(benzyloxy)propanal (20196-70-7) → (R)-2,3-diO-dibenzylglyceraldehyde (S)-α-methylbenzylimine (238401-88-2)

Guidance literature:

In diethyl ether;

DOI:10.1016/0040-4020(96)00493-0

Reference yield: 75.0%

danishefsky's diene (54125-02-9) + (R)-2,3-diO-dibenzylglyceraldehyde (S)-α-methylbenzylimine (238401-88-2) → (R)-N-[(S)-α-methylbenzyl]-2-[(S)-1,2-dibenzyloxyethyl]-5,6-dihydro-4-pyridone (238401-89-3)

Guidance literature:

With zinc(II) iodide; In acetonitrile; at -20 ℃; for 4h;

DOI:10.1016/S0040-4020(99)00377-4

Reference yield:

(R)-2,3-diO-dibenzylglyceraldehyde (S)-α-methylbenzylimine (238401-88-2) → (R)-N-tert-butoxycarbonyl-2-[(S)-1,2-dibenzyloxyethyl]-4-(1,3-dioxolane-2-yl)piperidine (238401-96-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 75 percent / ZnI₂ / acetonitrile / 4 h / -20 °C

2: 85 percent / L-selectride / tetrahydrofuran / 72 h / -78 °C

3: 82 percent / boron trifluoride etherate / CHCl₃ / 3 h / -10 - 20 °C

4: H₂ / 20 percent Pd(OH)2/C / ethanol / 3 h / 20 °C / 760 Torr

5: 70 percent / diisopropylethylamine / tetrahydrofuran / 20 h / 50 °C

With boron trifluoride diethyl etherate; hydrogen; L-Selectride; N-ethyl-N,N-diisopropylamine; zinc(II) iodide; palladium dihydroxide; In tetrahydrofuran; ethanol; chloroform; acetonitrile; 1: Cycloaddition / 2: Reduction / 3: Cycloaddition / 4: Hydrogenolysis / 5: Carboxylation;

DOI:10.1016/S0040-4020(99)00377-4

upstream raw materials:

(S)-1-phenyl-ethylamine

(+)-(R)-2,3-bis(benzyloxy)propanal

Downstream raw materials:

(R)-N-[(S)-α-methylbenzyl]-2-[(S)-1,2-dibenzyloxyethyl]-5,6-dihydro-4-pyridone

(R)-N-[(S)-α-methylbenzyl]-2-[(S)-1,2-dibenzyloxyethyl]-4-pyridone

(R)-N-tert-butoxycarbonyl-2-[(S)-1,2-dibenzyloxyethyl]-4-(1,3-dioxolane-2-yl)piperidine

(R)-N-[(S)-α-methylbenzyl]-2-[(S)-1,2-dibenzyloxyethyl]-4-(1,3-dioxolan-2-yl)piperidine