ethyl (3R,4R,5R)-3-benzoxy-4-(tert-butoxycarbonyl)amino-5-methanesulfonyloxy-1-cyclohexenecaboxylate

Base Information

• Chemical Name: ethyl (3R,4R,5R)-3-benzoxy-4-(tert-butoxycarbonyl)amino-5-methanesulfonyloxy-1-cyclohexenecaboxylate
• CAS No.: 1373390-68-1
• Molecular Formula: C₂₂H₃₁NO₈S
• Molecular Weight: 469.556
• Mol file: 1373390-68-1.mol

Synonyms:ethyl (3R,4R,5R)-3-benzoxy-4-(tert-butoxycarbonyl)amino-5-methanesulfonyloxy-1-cyclohexenecaboxylate

Chemical Property of ethyl (3R,4R,5R)-3-benzoxy-4-(tert-butoxycarbonyl)amino-5-methanesulfonyloxy-1-cyclohexenecaboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (3R,4R,5R)-3-benzoxy-4-(tert-butoxycarbonyl)amino-5-methanesulfonyloxy-1-cyclohexenecaboxylate

There total 4 articles about ethyl (3R,4R,5R)-3-benzoxy-4-(tert-butoxycarbonyl)amino-5-methanesulfonyloxy-1-cyclohexenecaboxylate 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: 80.0%

ethyl (3R,4R,5R)-3-benzoxy-4-(tert-butoxycarbonyl)amino-5-hydroxy-1-cyclohexenecaboxylate (1373390-64-7) + methanesulfonyl chloride (124-63-0) → ethyl (3R,4R,5R)-3-benzoxy-4-(tert-butoxycarbonyl)amino-5-methanesulfonyloxy-1-cyclohexenecaboxylate (1373390-68-1)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 25 ℃; for 1h;

DOI:10.1002/jccs.201100637

Reference yield:

tert-butyl (4S)-4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (108149-63-9,108149-65-1) → ethyl (3R,4R,5R)-3-benzoxy-4-(tert-butoxycarbonyl)amino-5-methanesulfonyloxy-1-cyclohexenecaboxylate (1373390-68-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 2 h / -78 °C

2.1: methyllithium / diethyl ether / 15 h / 0 °C

2.2: 1 h / 20 °C

2.3: 2.33 h / -78 - 20 °C

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 25 °C

4.1: toluene-4-sulfonic acid / methanol / 3 h / 25 °C

5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.25 h / -78 °C

5.2: 0.58 h / 0 °C

6.1: indium / ethanol; water / 6 h / 25 °C

7.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 3 h / Reflux

8.1: triethylamine / dichloromethane / 1 h / 0 - 25 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; indium; oxalyl dichloride; methyllithium; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil; 1.1: Swern oxidation / 5.1: Swern oxidation / 5.2: Swern oxidation / 6.1: Reformatsky reaction;

DOI:10.1002/jccs.201100637

Reference yield:

methyl [(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]carboxylate (108149-60-6,95715-86-9) → ethyl (3R,4R,5R)-3-benzoxy-4-(tert-butoxycarbonyl)amino-5-methanesulfonyloxy-1-cyclohexenecaboxylate (1373390-68-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.67 h / 25 °C

2.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 2 h / -78 °C

3.1: methyllithium / diethyl ether / 15 h / 0 °C

3.2: 1 h / 20 °C

3.3: 2.33 h / -78 - 20 °C

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 25 °C

5.1: toluene-4-sulfonic acid / methanol / 3 h / 25 °C

6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.25 h / -78 °C

6.2: 0.58 h / 0 °C

7.1: indium / ethanol; water / 6 h / 25 °C

8.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 3 h / Reflux

9.1: triethylamine / dichloromethane / 1 h / 0 - 25 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; indium; lithium aluminium tetrahydride; oxalyl dichloride; methyllithium; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil; 2.1: Swern oxidation / 6.1: Swern oxidation / 6.2: Swern oxidation / 7.1: Reformatsky reaction;

DOI:10.1002/jccs.201100637

upstream raw materials:

ethyl (3R,4R,5R)-3-benzoxy-4-(tert-butoxycarbonyl)amino-5-hydroxy-1-cyclohexenecaboxylate

methanesulfonyl chloride

tert-butyl (4S)-4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

methyl [(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]carboxylate

Refernces