(2S,3S)-methyl 2,3-O-isopropylidene-2-[(S)-1-hydroxy-3-phenyl-2-propynyl]pentanoate

Base Information

• Chemical Name: (2S,3S)-methyl 2,3-O-isopropylidene-2-[(S)-1-hydroxy-3-phenyl-2-propynyl]pentanoate
• CAS No.: 474915-71-4
• Molecular Formula: C₁₈H₂₂O₅
• Molecular Weight: 318.37

Synonyms:(2S,3S)-methyl 2,3-O-isopropylidene-2-[(S)-1-hydroxy-3-phenyl-2-propynyl]pentanoate

Chemical Property of (2S,3S)-methyl 2,3-O-isopropylidene-2-[(S)-1-hydroxy-3-phenyl-2-propynyl]pentanoate

Chemical Property:

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Technology Process of (2S,3S)-methyl 2,3-O-isopropylidene-2-[(S)-1-hydroxy-3-phenyl-2-propynyl]pentanoate

There total 2 articles about (2S,3S)-methyl 2,3-O-isopropylidene-2-[(S)-1-hydroxy-3-phenyl-2-propynyl]pentanoate 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: 69.0%

(3S)-1-tert-butyldimethylsiloxy-2,3-O-isopropylidene-1-methoxy-1-pentene + Phenylpropargyl aldehyde (2579-22-8) → (4S,5S)-5-Ethyl-4-((R)-1-hydroxy-3-phenyl-prop-2-ynyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester + (2S,3S)-methyl 2,3-O-isopropylidene-2-[(S)-1-hydroxy-3-phenyl-2-propynyl]pentanoate (474915-71-4)

Guidance literature:

With magnesium bromide; In dichloromethane; at -78 ℃; for 0.25h;

DOI:10.1021/ja0276826

Reference yield:

(4R,5S)-5-Ethyl-2,2-dimethyl-4-(3-phenyl-propynoyl)-[1,3]dioxolane-4-carboxylic acid methyl ester → (4S,5S)-5-Ethyl-4-((R)-1-hydroxy-3-phenyl-prop-2-ynyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester + (2S,3S)-methyl 2,3-O-isopropylidene-2-[(S)-1-hydroxy-3-phenyl-2-propynyl]pentanoate (474915-71-4)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In ethanol;

DOI:10.1021/ja0276826

Reference yield: 98.0%

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) + (2S,3S)-methyl 2,3-O-isopropylidene-2-[(S)-1-hydroxy-3-phenyl-2-propynyl]pentanoate (474915-71-4) → (2R,3S)-methyl 2,3-O-isopropylidene-2-[(S)-1-triisopropylsiloxy-3-phenyl-2-propynyl]pentanoate (474915-75-8)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 20 ℃; for 13h;

DOI:10.1021/ja0276826

upstream raw materials:

Phenylpropargyl aldehyde

Downstream raw materials:

(2R,3S)-methyl 2,3-O-isopropylidene-2-[(S)-1-triisopropylsiloxy-3-phenyl-2-propynyl]pentanoate

(4R,5S)-4-((S)-1-Benzyloxy-3-phenyl-prop-2-ynyl)-5-ethyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester

(4R,5S)-4-((S)-1-Benzyloxy-3-phenyl-prop-2-ynyl)-5-ethyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid amide

(4R,5S)-4-((S)-1-Benzyloxy-3-phenyl-prop-2-ynyl)-5-ethyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid

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