bis{3-[(S)-5-hydroxy(diphenyl)methyl-1-methyl-trans-3-azolanyloxy]propyl} bicyclo[2.2.1]hept-5-ene-(2-endo,3-endo)-dicarboxylate

Base Information

Chemical Name:bis{3-[(S)-5-hydroxy(diphenyl)methyl-1-methyl-trans-3-azolanyloxy]propyl} bicyclo[2.2.1]hept-5-ene-(2-endo,3-endo)-dicarboxylate
CAS No.:475271-41-1
Molecular Formula:C₅₁H₆₀N₂O₈
Molecular Weight:829.046
Hs Code.:

Synonyms:bis{3-[(S)-5-hydroxy(diphenyl)methyl-1-methyl-trans-3-azolanyloxy]propyl} bicyclo[2.2.1]hept-5-ene-(2-endo,3-endo)-dicarboxylate

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Chemical Property of bis{3-[(S)-5-hydroxy(diphenyl)methyl-1-methyl-trans-3-azolanyloxy]propyl} bicyclo[2.2.1]hept-5-ene-(2-endo,3-endo)-dicarboxylate

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Technology Process of bis{3-[(S)-5-hydroxy(diphenyl)methyl-1-methyl-trans-3-azolanyloxy]propyl} bicyclo[2.2.1]hept-5-ene-(2-endo,3-endo)-dicarboxylate

There total 3 articles about bis{3-[(S)-5-hydroxy(diphenyl)methyl-1-methyl-trans-3-azolanyloxy]propyl} bicyclo[2.2.1]hept-5-ene-(2-endo,3-endo)-dicarboxylate 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: 63.0%

: 129-64-6
3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

: 475271-38-6
3[(5S,3R)-5-hydroxy(diphenyl)methyl-1-methylazolan-3-yloxy]-1-propanol

: 475271-41-1
bis{3-[(S)-5-hydroxy(diphenyl)methyl-1-methyl-trans-3-azolanyloxy]propyl} bicyclo[2.2.1]hept-5-ene-(2-endo,3-endo)-dicarboxylate

Guidance literature:: With dmap; 2-chloro-1-methyl-pyridinium iodide; triethylamine; In dichloromethane; at 20 ℃; for 48h;
DOI:10.1002/1615-4169(200208)344:6/7<649::AID-ADSC649>3.0.CO;2-X

Reference yield:

: 172947-84-1
(2S,4R)-diphenyl-(1-methyl-4-hydroxypyrrolidin-2-yl)methanol

: 475271-41-1
bis{3-[(S)-5-hydroxy(diphenyl)methyl-1-methyl-trans-3-azolanyloxy]propyl} bicyclo[2.2.1]hept-5-ene-(2-endo,3-endo)-dicarboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaH / dimethylformamide / 2 h / 20 °C

1.2: 65 percent / dimethylformamide

2.1: catecholborane / tetrahydrofuran / 96 h / 20 °C

2.2: 69 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran

3.1: 63 percent / Et₃N; 4-DMAP; 2-chloro-1-methylpyridinium iodide / CH₂Cl₂ / 48 h / 20 °C

With dmap; 2-chloro-1-methyl-pyridinium iodide; sodium hydride; triethylamine; benzo[1,3,2]dioxaborole; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 3.1: Mukaiyama esterification;
DOI:10.1002/1615-4169(200208)344:6/7<649::AID-ADSC649>3.0.CO;2-X

Reference yield:

: (2S,4R)-4-allyloxy-1-methylazolan-2-yl(diphenyl)methylalcohol

: 475271-41-1
bis{3-[(S)-5-hydroxy(diphenyl)methyl-1-methyl-trans-3-azolanyloxy]propyl} bicyclo[2.2.1]hept-5-ene-(2-endo,3-endo)-dicarboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: catecholborane / tetrahydrofuran / 96 h / 20 °C

1.2: 69 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran

2.1: 63 percent / Et₃N; 4-DMAP; 2-chloro-1-methylpyridinium iodide / CH₂Cl₂ / 48 h / 20 °C

With dmap; 2-chloro-1-methyl-pyridinium iodide; triethylamine; benzo[1,3,2]dioxaborole; In tetrahydrofuran; dichloromethane; 2.1: Mukaiyama esterification;
DOI:10.1002/1615-4169(200208)344:6/7<649::AID-ADSC649>3.0.CO;2-X