ethyl (3R,4S,5S)-4-(tert-butoxycarbonyl)amino-3-(4-methoxybenzoxy)-5-methanesulfonyloxy-1-cyclohexencarboxylate

Base Information

Chemical Name:ethyl (3R,4S,5S)-4-(tert-butoxycarbonyl)amino-3-(4-methoxybenzoxy)-5-methanesulfonyloxy-1-cyclohexencarboxylate
CAS No.:1373390-67-0
Molecular Formula:C₂₃H₃₃NO₉S
Molecular Weight:499.582
Hs Code.:

Synonyms:ethyl (3R,4S,5S)-4-(tert-butoxycarbonyl)amino-3-(4-methoxybenzoxy)-5-methanesulfonyloxy-1-cyclohexencarboxylate

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Chemical Property of ethyl (3R,4S,5S)-4-(tert-butoxycarbonyl)amino-3-(4-methoxybenzoxy)-5-methanesulfonyloxy-1-cyclohexencarboxylate

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Technology Process of ethyl (3R,4S,5S)-4-(tert-butoxycarbonyl)amino-3-(4-methoxybenzoxy)-5-methanesulfonyloxy-1-cyclohexencarboxylate

There total 9 articles about ethyl (3R,4S,5S)-4-(tert-butoxycarbonyl)amino-3-(4-methoxybenzoxy)-5-methanesulfonyloxy-1-cyclohexencarboxylate 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: 96.0%

: 1373390-63-6
ethyl (3R,4R,5S)-4-(tert-butoxycarbonyl)amino-5-hydroxy-(4-methoxybenzoxy)-1-cyclohexenecarboxylate

: 124-63-0
methanesulfonyl chloride

: 1373390-67-0
ethyl (3R,4S,5S)-4-(tert-butoxycarbonyl)amino-3-(4-methoxybenzoxy)-5-methanesulfonyloxy-1-cyclohexencarboxylate

Guidance literature:: With triethylamine; In dichloromethane; at 0 - 25 ℃; for 1h;
DOI:10.1002/jccs.201100637

Reference yield:

: C₂₁H₃₁NO₅

: 1373390-67-0
ethyl (3R,4S,5S)-4-(tert-butoxycarbonyl)amino-3-(4-methoxybenzoxy)-5-methanesulfonyloxy-1-cyclohexencarboxylate

Guidance literature:: Multi-step reaction with 5 steps

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

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

2.2: 0.58 h / 0 °C

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

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

5.1: 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; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In methanol; ethanol; dichloromethane; water; 2.1: Swern oxidation / 2.2: Swern oxidation / 3.1: Reformatsky reaction;
DOI:10.1002/jccs.201100637

Reference yield:

: (2R,3R)-2-(tert-butoxycarbonyl)amino-3-(4-methoxybenzoxy)-4-penten-1-ol

: 1373390-67-0
ethyl (3R,4S,5S)-4-(tert-butoxycarbonyl)amino-3-(4-methoxybenzoxy)-5-methanesulfonyloxy-1-cyclohexencarboxylate

Guidance literature:: Multi-step reaction with 4 steps

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

1.2: 0.58 h / 0 °C

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

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

4.1: 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; dimethyl sulfoxide; triethylamine; In ethanol; dichloromethane; water; 1.1: Swern oxidation / 1.2: Swern oxidation / 2.1: Reformatsky reaction;
DOI:10.1002/jccs.201100637