methyl (1R,4S,5R)-1,4-dihydroxy-3-(thien-2-yl)methoxy-2-(thien-2-yl)methylcyclohex-2-ene-1-carboxylate

Base Information

• Chemical Name: methyl (1R,4S,5R)-1,4-dihydroxy-3-(thien-2-yl)methoxy-2-(thien-2-yl)methylcyclohex-2-ene-1-carboxylate
• CAS No.: 1319745-69-1
• Molecular Formula: C₁₈H₂₀O₆S₂
• Molecular Weight: 396.485

Synonyms:methyl (1R,4S,5R)-1,4-dihydroxy-3-(thien-2-yl)methoxy-2-(thien-2-yl)methylcyclohex-2-ene-1-carboxylate

Chemical Property of methyl (1R,4S,5R)-1,4-dihydroxy-3-(thien-2-yl)methoxy-2-(thien-2-yl)methylcyclohex-2-ene-1-carboxylate

Chemical Property:

Purity/Quality:

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MSDS Files:

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Technology Process of methyl (1R,4S,5R)-1,4-dihydroxy-3-(thien-2-yl)methoxy-2-(thien-2-yl)methylcyclohex-2-ene-1-carboxylate

There total 4 articles about methyl (1R,4S,5R)-1,4-dihydroxy-3-(thien-2-yl)methoxy-2-(thien-2-yl)methylcyclohex-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: 51.0%

(1R,4S,5R)-1,4-dihydroxy-3-(thien-3-yl)methoxy-2-(thien-3-yl)methylcyclohex-2-ene-1,5-carbolactone (1233376-32-3) + sodium methylate (124-41-4) → methyl (1R,4S,5R)-1,4-dihydroxy-3-(thien-2-yl)methoxy-2-(thien-2-yl)methylcyclohex-2-ene-1-carboxylate (1319745-69-1)

Guidance literature:

In methanol; at 20 ℃; for 0.5h;

DOI:10.1021/jm2006063

Reference yield:

2-thenyl bromide (45438-73-1) → methyl (1R,4S,5R)-1,4-dihydroxy-3-(thien-2-yl)methoxy-2-(thien-2-yl)methylcyclohex-2-ene-1-carboxylate (1319745-69-1)

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 / 1 h / 0 °C

3.1: methanol / 0.5 h / 20 °C

With tetrabutyl ammonium fluoride; potassium hexamethylsilazane; In tetrahydrofuran; methanol; 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) → methyl (1R,4S,5R)-1,4-dihydroxy-3-(thien-2-yl)methoxy-2-(thien-2-yl)methylcyclohex-2-ene-1-carboxylate (1319745-69-1)

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 / 1 h / 0 °C

3.1: methanol / 0.5 h / 20 °C

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

DOI:10.1021/jm2006063

upstream raw materials:

(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)methoxy-2-(thien-3-yl)methylcyclohex-2-en-1,5-carbolactone

(1R,4S,5R)-1,4-dihydroxy-3-(thien-3-yl)methoxy-2-(thien-3-yl)methylcyclohex-2-ene-1,5-carbolactone

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