(4R,5S)-4-ethynyl-5-[(4-methoxyphenoxy)methyl]-2,2-dimethyl-1,3-dioxolane

Base Information

• Chemical Name: (4R,5S)-4-ethynyl-5-[(4-methoxyphenoxy)methyl]-2,2-dimethyl-1,3-dioxolane
• CAS No.: 1439510-53-8
• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.306

Synonyms:(4R,5S)-4-ethynyl-5-[(4-methoxyphenoxy)methyl]-2,2-dimethyl-1,3-dioxolane

Chemical Property of (4R,5S)-4-ethynyl-5-[(4-methoxyphenoxy)methyl]-2,2-dimethyl-1,3-dioxolane

Chemical Property:

Purity/Quality:

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Technology Process of (4R,5S)-4-ethynyl-5-[(4-methoxyphenoxy)methyl]-2,2-dimethyl-1,3-dioxolane

There total 2 articles about (4R,5S)-4-ethynyl-5-[(4-methoxyphenoxy)methyl]-2,2-dimethyl-1,3-dioxolane 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: 66.0%

[(4S,5R)-5-ethynyl-2,2-dimethyl-1,3-dioxolan-4-yl]methanol (127305-55-9) + 4-methoxy-phenol (150-76-5) → (4R,5S)-4-ethynyl-5-[(4-methoxyphenoxy)methyl]-2,2-dimethyl-1,3-dioxolane (1439510-53-8)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In toluene; at 0 - 70 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ol401231y

Reference yield:

2,3-O-isopropylidene-L-erythrofuranose (213767-09-0) → (4R,5S)-4-ethynyl-5-[(4-methoxyphenoxy)methyl]-2,2-dimethyl-1,3-dioxolane (1439510-53-8)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium diisopropyl amide / tetrahydrofuran / -78 - 20 °C / Inert atmosphere

2: triphenylphosphine; diethylazodicarboxylate / toluene / 1 h / 0 - 70 °C / Inert atmosphere

With triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; toluene; 2: |Mitsunobu Displacement;

DOI:10.1021/ol401231y

Reference yield:

(4R,5S)-4-ethynyl-5-[(4-methoxyphenoxy)methyl]-2,2-dimethyl-1,3-dioxolane (1439510-53-8) → C12H14O4

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 20 ℃; for 17h; Inert atmosphere;

DOI:10.1021/ol401231y

upstream raw materials:

[(4S,5R)-5-ethynyl-2,2-dimethyl-1,3-dioxolan-4-yl]methanol

4-methoxy-phenol

2,3-O-isopropylidene-L-erythrofuranose

Downstream raw materials:

(4R,5S)-4-ethynyl-5-[(4-methoxyphenoxy)methyl]-1,3-dioxolan-2-one

(4R,5S)-4-(iodoethynyl)-5-[(4-methoxyphenoxy)methyl]-1,3-dioxolan-2-one

O-(1-{(4R,5R)-2,2-dimethyl-5-[(E)-pent-2-en-1-yl]-1,3-dioxolan-4-yl}-3-{(4R,5S)-5-[(4-methoxyphenoxy)methyl]-2-oxo-1,3-dioxolan-4-yl}prop-2-yn-1-yl) O-phenyl carbothioate

(4R,5S)-4-[3-((4S,5R)-5-{(2S,3S)-3-[(tert-butyldiphenylsilyl)oxy]-2-hydroxypentyl}-2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-yn-1-yl]-5-[(4-methoxyphenoxy)methyl]-1,3-dioxolan-2-one

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