dimethyl (3-(1S,4S,5R)-1,5-di[(methoxymethoxy)methyl]-4,5-dimethyl-6-oxo-2-cyclohexenyl-2-oxopropyl)phosphonate

Base Information

• Chemical Name: dimethyl (3-(1S,4S,5R)-1,5-di[(methoxymethoxy)methyl]-4,5-dimethyl-6-oxo-2-cyclohexenyl-2-oxopropyl)phosphonate
• CAS No.: 1395878-50-8
• Molecular Formula: C₁₉H₃₃O₉P
• Molecular Weight: 436.439

Synonyms:dimethyl (3-(1S,4S,5R)-1,5-di[(methoxymethoxy)methyl]-4,5-dimethyl-6-oxo-2-cyclohexenyl-2-oxopropyl)phosphonate

Chemical Property of dimethyl (3-(1S,4S,5R)-1,5-di[(methoxymethoxy)methyl]-4,5-dimethyl-6-oxo-2-cyclohexenyl-2-oxopropyl)phosphonate

Chemical Property:

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Technology Process of dimethyl (3-(1S,4S,5R)-1,5-di[(methoxymethoxy)methyl]-4,5-dimethyl-6-oxo-2-cyclohexenyl-2-oxopropyl)phosphonate

There total 8 articles about dimethyl (3-(1S,4S,5R)-1,5-di[(methoxymethoxy)methyl]-4,5-dimethyl-6-oxo-2-cyclohexenyl-2-oxopropyl)phosphonate 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: 95.0%

ethyl 2-(1S,4S,5R)-1,5-di[(methoxymethoxy)methyl]-4,5-dimethyl-6-oxo-2-cyclohexenylacetate (1395878-49-5) + dimethyl methane phosphonate (756-79-6) → dimethyl (3-(1S,4S,5R)-1,5-di[(methoxymethoxy)methyl]-4,5-dimethyl-6-oxo-2-cyclohexenyl-2-oxopropyl)phosphonate (1395878-50-8)

Guidance literature:

dimethyl methane phosphonate; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.583333h; Inert atmosphere;

ethyl 2-(1S,4S,5R)-1,5-di[(methoxymethoxy)methyl]-4,5-dimethyl-6-oxo-2-cyclohexenylacetate; In tetrahydrofuran; at -78 ℃; for 1h; chemoselective reaction; Inert atmosphere;

DOI:10.1021/jo301258g

Reference yield:

(4R,5R,6R)-4-hydroxy-2,6-di[(methoxymethoxy)methyl]-5,6-dimethyl-2-cyclohexen-1-one (1395878-47-3) → dimethyl (3-(1S,4S,5R)-1,5-di[(methoxymethoxy)methyl]-4,5-dimethyl-6-oxo-2-cyclohexenyl-2-oxopropyl)phosphonate (1395878-50-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: propionic acid / Sealed tube; Inert atmosphere; Heating

2.1: n-butyllithium / tetrahydrofuran / 0.58 h / -78 °C / Inert atmosphere

2.2: 1 h / -78 °C / Inert atmosphere

With n-butyllithium; propionic acid; In tetrahydrofuran; 1.1: |Johnson-Claisen Rearrangement;

DOI:10.1021/jo301258g

Reference yield:

(2S,5R,6S,7R)-6-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-5-methyltricyclo[6.2.1.02,7]undec-9-en-3-one (1395878-42-8) → dimethyl (3-(1S,4S,5R)-1,5-di[(methoxymethoxy)methyl]-4,5-dimethyl-6-oxo-2-cyclohexenyl-2-oxopropyl)phosphonate (1395878-50-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.25 h / -78 - -20 °C / Inert atmosphere

1.2: 1 h / -78 - 0 °C / Inert atmosphere

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran; water / 12 h / 25 °C / Cooling with ice

3.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 25 °C / Cooling with ice

4.1: diphenylether / 0.25 h / Heating; Inert atmosphere

5.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 10 h / 25 °C / Inert atmosphere

6.1: propionic acid / Sealed tube; Inert atmosphere; Heating

7.1: n-butyllithium / tetrahydrofuran / 0.58 h / -78 °C / Inert atmosphere

7.2: 1 h / -78 °C / Inert atmosphere

With dmap; n-butyllithium; tetrabutyl ammonium fluoride; acetic acid; propionic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; diphenylether; dichloromethane; water; 6.1: |Johnson-Claisen Rearrangement;

DOI:10.1021/jo301258g

upstream raw materials:

ethyl 2-(1S,4S,5R)-1,5-di[(methoxymethoxy)methyl]-4,5-dimethyl-6-oxo-2-cyclohexenylacetate

dimethyl methane phosphonate

(4R,5R,6R)-4-hydroxy-2,6-di[(methoxymethoxy)methyl]-5,6-dimethyl-2-cyclohexen-1-one

(2S,5R,6S,7R)-6-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-5-methyltricyclo[6.2.1.0^2,7]undec-9-en-3-one

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