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

Base Information

• Chemical Name: ethyl (2S,1'S,2'R,3'R)-N-(tert-butoxycarbonyl)-2-[3'-benzyloxymethyl-2'-(ethoxycarbonyl)cyclopropyl] glycinate
• CAS No.: 653598-82-4
• Molecular Formula: C₂₃H₃₃NO₇
• Molecular Weight: 435.518
• Mol file: 653598-82-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about ethyl (2S,1'S,2'R,3'R)-N-(tert-butoxycarbonyl)-2-[3'-benzyloxymethyl-2'-(ethoxycarbonyl)cyclopropyl] glycinate 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:

di-tert-butyl dicarbonate (24424-99-5) + (1R,2S,3R)-2-((S)-Amino-ethoxycarbonyl-methyl)-3-benzyloxymethyl-cyclopropanecarboxylic acid ethyl ester → ethyl (2S,1'S,2'R,3'R)-N-(tert-butoxycarbonyl)-2-[3'-benzyloxymethyl-2'-(ethoxycarbonyl)cyclopropyl] glycinate (653598-82-4)

Guidance literature:

With sodium hydrogencarbonate; In 1,4-dioxane; at 20 ℃;

DOI:10.1021/jm030967o

Reference yield:

(Z)-4-benzyloxy-but-2-en-1-ol (81028-03-7) → ethyl (2S,1'S,2'R,3'R)-N-(tert-butoxycarbonyl)-2-[3'-benzyloxymethyl-2'-(ethoxycarbonyl)cyclopropyl] glycinate (653598-82-4)

Guidance literature:

Multi-step reaction with 13 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

12.1: Pb(OAc)4 / CH₂Cl₂; methanol / 0.17 h / 0 °C

12.2: aq. HCl / 18 h / 20 °C

13.1: 0.11 g / aq. NaHCO₃ / dioxane / 20 °C

With 1H-imidazole; lead(IV) acetate; lithium hydroxide; tetrapropylammonium perruthennate; Rh₂(4S-MPPIM)4; 4-acetamidobenzenesulfonyl azide; tetrabutyl ammonium fluoride; sodium acetate; potassium hexamethylsilazane; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; 1,4-dioxane; 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) → ethyl (2S,1'S,2'R,3'R)-N-(tert-butoxycarbonyl)-2-[3'-benzyloxymethyl-2'-(ethoxycarbonyl)cyclopropyl] glycinate (653598-82-4)

Guidance literature:

Multi-step reaction with 10 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

9.1: Pb(OAc)4 / CH₂Cl₂; methanol / 0.17 h / 0 °C

9.2: aq. HCl / 18 h / 20 °C

10.1: 0.11 g / aq. NaHCO₃ / dioxane / 20 °C

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

DOI:10.1021/jm030967o

upstream raw materials:

di-tert-butyl dicarbonate

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

diazoacetic acid 4-benzyloxy-but-2-enyl ester

(1R,5S,6R)-6-(benzyloxymethyl)-3-oxabicyclo[3.1.0]hexan-2-one