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

Base Information

Chemical Name:(2R,3S)-2-{3-[(S)-5-hydroxy(diphenyl)methyl-1-methyl-trans-3-azolanyloxy]propyl} 3-methyl bicyclo[2.2.1]hept-5-ene-(2-endo,3-endo)-dicarboxylate
CAS No.:475271-43-3
Molecular Formula:C₃₁H₃₇NO₆
Molecular Weight:519.638
Hs Code.:

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

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

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

There total 3 articles about (2R,3S)-2-{3-[(S)-5-hydroxy(diphenyl)methyl-1-methyl-trans-3-azolanyloxy]propyl} 3-methyl 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: 68.0%

: 96243-74-2
(1S,2R,3S,4R)-3-(methoxycarbonyl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

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

: 475271-43-3
(2R,3S)-2-{3-[(S)-5-hydroxy(diphenyl)methyl-1-methyl-trans-3-azolanyloxy]propyl} 3-methyl bicyclo[2.2.1]hept-5-ene-(2-endo,3-endo)-dicarboxylate

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; 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

: 475271-43-3
(2R,3S)-2-{3-[(S)-5-hydroxy(diphenyl)methyl-1-methyl-trans-3-azolanyloxy]propyl} 3-methyl 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: 68 percent / dicyclohexylcarbodiimide; 4-DMAP / CH₂Cl₂ / 48 h / 20 °C

With dmap; sodium hydride; dicyclohexyl-carbodiimide; benzo[1,3,2]dioxaborole; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
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

: 475271-43-3
(2R,3S)-2-{3-[(S)-5-hydroxy(diphenyl)methyl-1-methyl-trans-3-azolanyloxy]propyl} 3-methyl 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: 68 percent / dicyclohexylcarbodiimide; 4-DMAP / CH₂Cl₂ / 48 h / 20 °C

With dmap; dicyclohexyl-carbodiimide; benzo[1,3,2]dioxaborole; In tetrahydrofuran; dichloromethane;
DOI:10.1002/1615-4169(200208)344:6/7<649::AID-ADSC649>3.0.CO;2-X