ethyl (1R,4S,5R)-3-(benzo[b]thiophen-5-yl)methoxyl-1,4,5-trihydroxycyclohex-2-ene-1-carboxylate

Base Information

Chemical Name:ethyl (1R,4S,5R)-3-(benzo[b]thiophen-5-yl)methoxyl-1,4,5-trihydroxycyclohex-2-ene-1-carboxylate
CAS No.:1319745-61-3
Molecular Formula:C₁₈H₂₀O₆S
Molecular Weight:364.419
Hs Code.:

Synonyms:ethyl (1R,4S,5R)-3-(benzo[b]thiophen-5-yl)methoxyl-1,4,5-trihydroxycyclohex-2-ene-1-carboxylate

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Chemical Property of ethyl (1R,4S,5R)-3-(benzo[b]thiophen-5-yl)methoxyl-1,4,5-trihydroxycyclohex-2-ene-1-carboxylate

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Technology Process of ethyl (1R,4S,5R)-3-(benzo[b]thiophen-5-yl)methoxyl-1,4,5-trihydroxycyclohex-2-ene-1-carboxylate

There total 5 articles about ethyl (1R,4S,5R)-3-(benzo[b]thiophen-5-yl)methoxyl-1,4,5-trihydroxycyclohex-2-ene-1-carboxylate 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: 58.0%

: 74-96-4
ethyl bromide

: 1198790-98-5
sodium (1R,4S,5R)-1,4,5-trihydroxy-3-[(benzo[b]thiophen-5-yl)methoxy]cyclohex-2-en-1-carboxylate

: 1319745-61-3
ethyl (1R,4S,5R)-3-(benzo[b]thiophen-5-yl)methoxyl-1,4,5-trihydroxycyclohex-2-ene-1-carboxylate

Guidance literature:: sodium (1R,4S,5R)-1,4,5-trihydroxy-3-[(benzo[b]thiophen-5-yl)methoxy]cyclohex-2-en-1-carboxylate; With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

ethyl bromide; In N,N-dimethyl-formamide; for 2h;
DOI:10.1021/jm2006063

Reference yield:

: 862791-12-6
(1R,4S,5R)-1,4-bis(tert-butyldimethylsilyloxy)-3-oxocyclohexane-1,5-carbolactone

: 1319745-61-3
ethyl (1R,4S,5R)-3-(benzo[b]thiophen-5-yl)methoxyl-1,4,5-trihydroxycyclohex-2-ene-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: potassium hexamethylsilazane / N,N-dimethyl-formamide; toluene / -78 °C / Inert atmosphere

1.2: Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 °C

3.1: sodium hydroxide / tetrahydrofuran / 20 °C

4.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C

4.2: 2 h

With tetrabutyl ammonium fluoride; potassium hexamethylsilazane; potassium carbonate; sodium hydroxide; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm2006063

Reference yield:

: 1198791-10-4
(1R,4S,5R)-3-(benzo[b]tiophen-5-yl)methoxy-1,4-dihydroxy-cyclohex-2-en-1,5-carbolactone

: 1319745-61-3
ethyl (1R,4S,5R)-3-(benzo[b]thiophen-5-yl)methoxyl-1,4,5-trihydroxycyclohex-2-ene-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydroxide / tetrahydrofuran / 20 °C

2.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C

2.2: 2 h

With potassium carbonate; sodium hydroxide; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/jm2006063