(2S,1'S,2'R,3'R,1''R)-N-[(2''-hydroxy-1''-phenyl)ethyl]-2-[3'-benzyloxymethyl-2'-(methoxycarbonyl)cyclopropyl] glycinonitrile

Base Information

• Chemical Name: (2S,1'S,2'R,3'R,1''R)-N-[(2''-hydroxy-1''-phenyl)ethyl]-2-[3'-benzyloxymethyl-2'-(methoxycarbonyl)cyclopropyl] glycinonitrile
• CAS No.: 653598-81-3
• Molecular Formula: C₂₃H₂₆N₂O₄
• Molecular Weight: 394.47
• Mol file: 653598-81-3.mol

Synonyms:(2S,1'S,2'R,3'R,1''R)-N-[(2''-hydroxy-1''-phenyl)ethyl]-2-[3'-benzyloxymethyl-2'-(methoxycarbonyl)cyclopropyl] glycinonitrile

Chemical Property of (2S,1'S,2'R,3'R,1''R)-N-[(2''-hydroxy-1''-phenyl)ethyl]-2-[3'-benzyloxymethyl-2'-(methoxycarbonyl)cyclopropyl] glycinonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,1'S,2'R,3'R,1''R)-N-[(2''-hydroxy-1''-phenyl)ethyl]-2-[3'-benzyloxymethyl-2'-(methoxycarbonyl)cyclopropyl] glycinonitrile

There total 11 articles about (2S,1'S,2'R,3'R,1''R)-N-[(2''-hydroxy-1''-phenyl)ethyl]-2-[3'-benzyloxymethyl-2'-(methoxycarbonyl)cyclopropyl] glycinonitrile 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:

(Z)-4-benzyloxy-but-2-en-1-ol (81028-03-7) → (2S,1'S,2'R,3'R,1''R)-N-[(2''-hydroxy-1''-phenyl)ethyl]-2-[3'-benzyloxymethyl-2'-(methoxycarbonyl)cyclopropyl] glycinonitrile (653598-81-3)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 91 percent / AcONa / tetrahydrofuran / 0.5 h / Heating

2.1: Et₃N; p-acetamidobenzenesulfonyl azide / acetonitrile / 2.5 h / 20 °C

3.1: 3.7 g / aq. LiOH / acetonitrile / 20 °C

4.1: 65 percent / Rh₂(4S-MPPIM)4 / CH₂Cl₂ / Heating

5.1: aq. LiOH / tetrahydrofuran / 2 h / 20 °C

6.1: 0.65 g / diethyl ether / 1 h / 0 °C

7.1: 88 percent / imidazole / dimethylformamide / 2 h / 20 °C

8.1: KHMDS / tetrahydrofuran; toluene / 2.67 h / -78 - -10 °C

9.1: 0.22 g / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 0 °C

10.1: 89 percent / tetra-n-propylammonium perruthenate; N-methylmorpholine N-oxide / CH₂Cl₂ / 20 °C

11.1: methanol / 2 h / 20 °C

11.2: 0.18 g / methanol / 20 °C

With 1H-imidazole; lithium hydroxide; tetrapropylammonium perruthennate; Rh₂(4S-MPPIM)4; 4-acetamidobenzenesulfonyl azide; tetrabutyl ammonium fluoride; sodium acetate; potassium hexamethylsilazane; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 11.1: Strecker synthesis;

DOI:10.1021/jm030967o

Reference yield:

diazoacetic acid 4-benzyloxy-but-2-enyl ester (181310-22-5) → (2S,1'S,2'R,3'R,1''R)-N-[(2''-hydroxy-1''-phenyl)ethyl]-2-[3'-benzyloxymethyl-2'-(methoxycarbonyl)cyclopropyl] glycinonitrile (653598-81-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 65 percent / Rh₂(4S-MPPIM)4 / CH₂Cl₂ / Heating

2.1: aq. LiOH / tetrahydrofuran / 2 h / 20 °C

3.1: 0.65 g / diethyl ether / 1 h / 0 °C

4.1: 88 percent / imidazole / dimethylformamide / 2 h / 20 °C

5.1: KHMDS / tetrahydrofuran; toluene / 2.67 h / -78 - -10 °C

6.1: 0.22 g / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 0 °C

7.1: 89 percent / tetra-n-propylammonium perruthenate; N-methylmorpholine N-oxide / CH₂Cl₂ / 20 °C

8.1: methanol / 2 h / 20 °C

8.2: 0.18 g / methanol / 20 °C

With 1H-imidazole; lithium hydroxide; tetrapropylammonium perruthennate; Rh₂(4S-MPPIM)4; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; 8.1: Strecker synthesis;

DOI:10.1021/jm030967o

Reference yield:

(1R,5S,6R)-6-(benzyloxymethyl)-3-oxabicyclo[3.1.0]hexan-2-one (653598-76-6) → (2S,1'S,2'R,3'R,1''R)-N-[(2''-hydroxy-1''-phenyl)ethyl]-2-[3'-benzyloxymethyl-2'-(methoxycarbonyl)cyclopropyl] glycinonitrile (653598-81-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: aq. LiOH / tetrahydrofuran / 2 h / 20 °C

2.1: 0.65 g / diethyl ether / 1 h / 0 °C

3.1: 88 percent / imidazole / dimethylformamide / 2 h / 20 °C

4.1: KHMDS / tetrahydrofuran; toluene / 2.67 h / -78 - -10 °C

5.1: 0.22 g / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 0 °C

6.1: 89 percent / tetra-n-propylammonium perruthenate; N-methylmorpholine N-oxide / CH₂Cl₂ / 20 °C

7.1: methanol / 2 h / 20 °C

7.2: 0.18 g / methanol / 20 °C

With 1H-imidazole; lithium hydroxide; tetrapropylammonium perruthennate; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; 7.1: Strecker synthesis;

DOI:10.1021/jm030967o

upstream raw materials:

trimethylsilyl cyanide

D-2-phenylglycinol

methyl (1S,2S,3R)-3-benzyloxymethyl-2-formylcyclopropane carboxylate

(Z)-4-benzyloxy-but-2-en-1-ol

Downstream raw materials:

ethyl (2S,1'S,2'R,3'R)-N-(tert-butoxycarbonyl)-2-[3'-benzyloxymethyl-2'-(ethoxycarbonyl)cyclopropyl] glycinate