sodium (1R,4S,5R)-1,4-dihydroxy-3-(thien-3-yl)methoxycyclohex-2-en-1-carboxylate

Base Information

• Chemical Name: sodium (1R,4S,5R)-1,4-dihydroxy-3-(thien-3-yl)methoxycyclohex-2-en-1-carboxylate
• CAS No.: 1198790-97-4
• Molecular Formula: C₁₂H₁₃O₆S*Na
• Molecular Weight: 308.287

Synonyms:sodium (1R,4S,5R)-1,4-dihydroxy-3-(thien-3-yl)methoxycyclohex-2-en-1-carboxylate

Chemical Property of sodium (1R,4S,5R)-1,4-dihydroxy-3-(thien-3-yl)methoxycyclohex-2-en-1-carboxylate

Chemical Property:

Purity/Quality:

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Technology Process of sodium (1R,4S,5R)-1,4-dihydroxy-3-(thien-3-yl)methoxycyclohex-2-en-1-carboxylate

There total 4 articles about sodium (1R,4S,5R)-1,4-dihydroxy-3-(thien-3-yl)methoxycyclohex-2-en-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: 97.0%

(1R,4S,5R)-1,4-dihydroxy-3-(thien-3-yl)methoxycyclohex-2-en-1,5-carbolactone (1198791-09-1) → sodium (1R,4S,5R)-1,4-dihydroxy-3-(thien-3-yl)methoxycyclohex-2-en-1-carboxylate (1198790-97-4)

Guidance literature:

With water; sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 0.25h;

DOI:10.1021/jm9010466

Reference yield:

2-thenyl bromide (45438-73-1) → sodium (1R,4S,5R)-1,4-dihydroxy-3-(thien-3-yl)methoxycyclohex-2-en-1-carboxylate (1198790-97-4)

Guidance literature:

Multi-step reaction with 3 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

With tetrabutyl ammonium fluoride; potassium hexamethylsilazane; sodium hydroxide; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm2006063

Reference yield:

(1R,4S,5R)-1,4-bis(tert-butyldimethylsilyloxy)-3-oxocyclohexane-1,5-carbolactone (862791-12-6) → sodium (1R,4S,5R)-1,4-dihydroxy-3-(thien-3-yl)methoxycyclohex-2-en-1-carboxylate (1198790-97-4)

Guidance literature:

Multi-step reaction with 3 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

With tetrabutyl ammonium fluoride; potassium hexamethylsilazane; sodium hydroxide; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm2006063

upstream raw materials:

(1R,4S,5R)-1,4-dihydroxy-3-(thien-3-yl)methoxycyclohex-2-en-1,5-carbolactone

(1R,4S,5R)-1,4-bis(tert-butyldimethylsilyloxy)-3-oxocyclohexane-1,5-carbolactone

2-thenyl bromide

(1R,4S,5R)-1,4-di(tert-butyldimethylsilyloxy)-3-(thien-3-yl)methoxycyclohex-2-en-1,5-carbolactone

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