phenyl (2R,3R)-2-benzyloxy-3-hydroxy-3-(2-oxyisoquinolin-3-yl)propionate

Base Information

• Chemical Name: phenyl (2R,3R)-2-benzyloxy-3-hydroxy-3-(2-oxyisoquinolin-3-yl)propionate
• CAS No.: 897942-95-9
• Molecular Formula: C₂₅H₂₁NO₅
• Molecular Weight: 415.445
• Mol file: 897942-95-9.mol

Synonyms:phenyl (2R,3R)-2-benzyloxy-3-hydroxy-3-(2-oxyisoquinolin-3-yl)propionate

Chemical Property of phenyl (2R,3R)-2-benzyloxy-3-hydroxy-3-(2-oxyisoquinolin-3-yl)propionate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl (2R,3R)-2-benzyloxy-3-hydroxy-3-(2-oxyisoquinolin-3-yl)propionate

There total 4 articles about phenyl (2R,3R)-2-benzyloxy-3-hydroxy-3-(2-oxyisoquinolin-3-yl)propionate 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: 80.0%

2-oxyisoquinoline-3-carbaldehyde (897942-84-6) + 2-(benzyloxy)-1-(trimethylsiloxy)-1-phenoxyethylene → phenyl (2R,3R)-2-benzyloxy-3-hydroxy-3-(2-oxyisoquinolin-3-yl)propionate (897942-95-9) + phenyl 2-benzyloxy-3-hydroxy-3-(2-oxyisoquinolin-3-yl)propionate

Guidance literature:

With copper(II) bis(trifluoromethanesulfonate); In dichloromethane; at -40 ℃;

DOI:10.1002/chem.200501475

Reference yield:

3-[1,3]dioxolan-2-ylisoquinoline 2-oxide (897943-17-8) → phenyl (2R,3R)-2-benzyloxy-3-hydroxy-3-(2-oxyisoquinolin-3-yl)propionate (897942-95-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 66 percent / aq. HCl

2: 80 percent / 2,2'-isopropylidinenebis[(4S)-4-tert-butyl-2-oxazoline]; Cu(OTf)2 / CH₂Cl₂ / -40 °C

With hydrogenchloride; copper(II) bis(trifluoromethanesulfonate); In dichloromethane; 2: asymmetric Mukaiyama aldol reaction;

DOI:10.1002/chem.200501475

Reference yield:

3-formylisoquinoline (5470-80-4) → phenyl (2R,3R)-2-benzyloxy-3-hydroxy-3-(2-oxyisoquinolin-3-yl)propionate (897942-95-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / p-TsOH / benzene / Heating

2: 93 percent / m-CPBA / CH₂Cl₂ / 6 h / 0 °C

3: 66 percent / aq. HCl

4: 80 percent / 2,2'-isopropylidinenebis[(4S)-4-tert-butyl-2-oxazoline]; Cu(OTf)2 / CH₂Cl₂ / -40 °C

With hydrogenchloride; copper(II) bis(trifluoromethanesulfonate); toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; benzene; 4: asymmetric Mukaiyama aldol reaction;

DOI:10.1002/chem.200501475

upstream raw materials:

2-oxyisoquinoline-3-carbaldehyde

3-[1,3]dioxolan-2-ylisoquinoline 2-oxide

3-formylisoquinoline

isoquinoline-3-carboxaldehyde ethylene glycol ketal

Downstream raw materials:

(1S,2R,10aS)-2-benzyloxy-1-hydroxy-1,5,10,10a-tetrahydro-2H-pyrrolo[1,2-b]isoquinolin-3-one