(1R,6R,9S)-2-(1,2-Dihydroxy-1-methyl-ethyl)-9-aza-bicyclo[4.2.1]non-2-ene-9-carboxylic acid benzyl ester

Base Information

• Chemical Name: (1R,6R,9S)-2-(1,2-Dihydroxy-1-methyl-ethyl)-9-aza-bicyclo[4.2.1]non-2-ene-9-carboxylic acid benzyl ester
• CAS No.: 690211-40-6
• Molecular Formula: C₁₉H₂₅NO₄
• Molecular Weight: 331.412
• Mol file: 690211-40-6.mol

Synonyms:(1R,6R,9S)-2-(1,2-Dihydroxy-1-methyl-ethyl)-9-aza-bicyclo[4.2.1]non-2-ene-9-carboxylic acid benzyl ester

Chemical Property of (1R,6R,9S)-2-(1,2-Dihydroxy-1-methyl-ethyl)-9-aza-bicyclo[4.2.1]non-2-ene-9-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,6R,9S)-2-(1,2-Dihydroxy-1-methyl-ethyl)-9-aza-bicyclo[4.2.1]non-2-ene-9-carboxylic acid benzyl ester

There total 11 articles about (1R,6R,9S)-2-(1,2-Dihydroxy-1-methyl-ethyl)-9-aza-bicyclo[4.2.1]non-2-ene-9-carboxylic acid benzyl ester 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: 76.0%

(1R,6R,9S)-2-Isopropenyl-9-aza-bicyclo[4.2.1]non-2-ene-9-carboxylic acid benzyl ester (690211-39-3) → (1R,6R,9S)-2-(1,2-Dihydroxy-1-methyl-ethyl)-9-aza-bicyclo[4.2.1]non-2-ene-9-carboxylic acid benzyl ester (690211-40-6) + (1R,6S,9S)-2,3-Dihydroxy-2-isopropenyl-9-aza-bicyclo[4.2.1]nonane-9-carboxylic acid benzyl ester

Guidance literature:

(1R,6R,9S)-2-Isopropenyl-9-aza-bicyclo[4.2.1]non-2-ene-9-carboxylic acid benzyl ester; With osmium(VIII) oxide; triethylamine; In tetrahydrofuran; at -78 - 20 ℃;

With sodium hydrogensulfite; In tetrahydrofuran; water; Heating;

DOI:10.1021/ol049631e

Reference yield: 76.0%

(+)-(1R)-2-isopropenyl-9-benzyloxycarbonyl-9-azabicyclo[4.2.1]-2-nonene (690211-39-3) → (+)-(1R)-2-(1,2-dihydroxy-1-methylethyl)-9-benzyloxycarbonyl-9-azabicyclo[4.2.1]-2-nonene (690211-40-6) + (1R,2R,6S)-2,3-Dihydroxy-2-isopropenyl-9-aza-bicyclo[4.2.1]nonane-9-carboxylic acid benzyl ester

Guidance literature:

With osmium(VIII) oxide; triethylamine; In tetrahydrofuran; at -78 - 20 ℃; for 22h;

DOI:10.1016/j.tet.2004.06.021

Reference yield:

(2R,5R)-5-but-3-enyl-2-ethynylpyrrolidine-1-carboxylic acid 1-benzyl ester (690211-37-1) → (1R,6R,9S)-2-(1,2-Dihydroxy-1-methyl-ethyl)-9-aza-bicyclo[4.2.1]non-2-ene-9-carboxylic acid benzyl ester (690211-40-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 97 percent / sodium hexamethyldisilazide / tetrahydrofuran / -78 °C

2.1: 87 percent / (1,3-dimesitylimidazolidin-2-yl)((c-Hex)3P)(Cl)2Ru=CHC₆H₅ / CH₂Cl₂ / 20 °C

3.1: osmium tetroxide; triethylamine / tetrahydrofuran / -78 - 20 °C

3.2: 76 percent / sodium hydrogen sulfite / tetrahydrofuran; H₂O / Heating

With osmium(VIII) oxide; sodium hexamethyldisilazane; triethylamine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol049631e

upstream raw materials:

(+)-(1R)-2-isopropenyl-9-benzyloxycarbonyl-9-azabicyclo[4.2.1]-2-nonene

methyl (2R)-pyroglutamate

benzyl chloroformate

1-benzyl 2-methyl (R)-5-oxopyrrolidine-1,2-dicarboxylate

Downstream raw materials:

(+)-(1R)-2-acetyl-9-benzyloxycarbonyl-9-azabicyclo[4.2.1]-2-nonene

(1R,6R,9S)-2-Acetyl-9-aza-bicyclo[4.2.1]non-2-ene-9-carboxylic acid benzyl ester

anatoxin-a