(2R)-3-[2,3-bis(methoxymethoxy)-4-methylphenyl]-2-methyl-3-oxopropyl (diethoxyphosphinyl)acetate

Base Information

• Chemical Name: (2R)-3-[2,3-bis(methoxymethoxy)-4-methylphenyl]-2-methyl-3-oxopropyl (diethoxyphosphinyl)acetate
• CAS No.: 519156-74-2
• Molecular Formula: C₂₁H₃₃O₁₀P
• Molecular Weight: 476.461

Synonyms:(2R)-3-[2,3-bis(methoxymethoxy)-4-methylphenyl]-2-methyl-3-oxopropyl (diethoxyphosphinyl)acetate

Chemical Property of (2R)-3-[2,3-bis(methoxymethoxy)-4-methylphenyl]-2-methyl-3-oxopropyl (diethoxyphosphinyl)acetate

Chemical Property:

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Technology Process of (2R)-3-[2,3-bis(methoxymethoxy)-4-methylphenyl]-2-methyl-3-oxopropyl (diethoxyphosphinyl)acetate

There total 2 articles about (2R)-3-[2,3-bis(methoxymethoxy)-4-methylphenyl]-2-methyl-3-oxopropyl (diethoxyphosphinyl)acetate 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: 91.0%

diethyl (2-chloro-2-oxoethyl)phosphonate (34170-81-5) + (R)-1-[2,3-bis(methoxymethoxy)-4-methylphenyl]-3-hydroxy-2-methylpropan-1-one (519156-77-5) → (2R)-3-[2,3-bis(methoxymethoxy)-4-methylphenyl]-2-methyl-3-oxopropyl (diethoxyphosphinyl)acetate (519156-74-2)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1055/s-2003-36269

Reference yield:

1,2-bis[methoxymethoxy]-3-methylbenzene (502506-85-6) → (2R)-3-[2,3-bis(methoxymethoxy)-4-methylphenyl]-2-methyl-3-oxopropyl (diethoxyphosphinyl)acetate (519156-74-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: BuLi / tetrahydrofuran; hexane / 2 h / 20 °C

1.2: 47 percent / tetrahydrofuran; hexane / 15 h / 20 °C

2.1: 91 percent / p-TsOH / tetrahydrofuran / 2 h / 0 °C

With n-butyllithium; toluene-4-sulfonic acid; In tetrahydrofuran; hexane; 2.1: Horner-Emmons reaction;

DOI:10.1055/s-2003-36269

Reference yield: 38.0%

(2R)-3-[2,3-bis(methoxymethoxy)-4-methylphenyl]-2-methyl-3-oxopropyl (diethoxyphosphinyl)acetate (519156-74-2) → 1-(2,3-bis-methoxymethoxy-4-methyl-phenyl)-2-methyl-propenone + (R)-1-[2,3-bis(methoxymethoxy)-4-methylphenyl]-3-hydroxy-2-methylpropan-1-one (519156-77-5) + (4S)-3-[2,3-bis(methoxymethoxy)-4-methylphenyl]-4-methyl-2,3-didehydro-δ-valerolactone (519156-73-1)

Guidance literature:

With triethylamine; lithium bromide; In acetonitrile; at 0 ℃; for 9h;

DOI:10.1055/s-2003-36269

upstream raw materials:

diethyl (2-chloro-2-oxoethyl)phosphonate

(R)-1-[2,3-bis(methoxymethoxy)-4-methylphenyl]-3-hydroxy-2-methylpropan-1-one

1,2-bis[methoxymethoxy]-3-methylbenzene

Downstream raw materials:

(R)-1-[2,3-bis(methoxymethoxy)-4-methylphenyl]-3-hydroxy-2-methylpropan-1-one

(4S)-3-[2,3-bis(methoxymethoxy)-4-methylphenyl]-4-methyl-2,3-didehydro-δ-valerolactone

(2S,3R,4R)-3-[2,3-bis(methoxymethoxy)-4-methylphenyl]-2,3-epoxy-4-methyl-δ-valerolactone

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