2-[(E)-3-((2R,4R,6S)-4-Benzyloxy-6-methoxy-3,3-dimethyl-tetrahydro-pyran-2-yl)-propenyl]-5-methoxy-oxazole-4-carboxylic acid methyl ester

Base Information

• Chemical Name: 2-[(E)-3-((2R,4R,6S)-4-Benzyloxy-6-methoxy-3,3-dimethyl-tetrahydro-pyran-2-yl)-propenyl]-5-methoxy-oxazole-4-carboxylic acid methyl ester
• CAS No.: 253800-09-8
• Molecular Formula: C₂₄H₃₁NO₇
• Molecular Weight: 445.513

Synonyms:2-[(E)-3-((2R,4R,6S)-4-Benzyloxy-6-methoxy-3,3-dimethyl-tetrahydro-pyran-2-yl)-propenyl]-5-methoxy-oxazole-4-carboxylic acid methyl ester

Chemical Property of 2-[(E)-3-((2R,4R,6S)-4-Benzyloxy-6-methoxy-3,3-dimethyl-tetrahydro-pyran-2-yl)-propenyl]-5-methoxy-oxazole-4-carboxylic acid methyl ester

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Technology Process of 2-[(E)-3-((2R,4R,6S)-4-Benzyloxy-6-methoxy-3,3-dimethyl-tetrahydro-pyran-2-yl)-propenyl]-5-methoxy-oxazole-4-carboxylic acid methyl ester

There total 2 articles about 2-[(E)-3-((2R,4R,6S)-4-Benzyloxy-6-methoxy-3,3-dimethyl-tetrahydro-pyran-2-yl)-propenyl]-5-methoxy-oxazole-4-carboxylic acid methyl ester 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: 65.0%

dimethyl diazomalonate (6773-29-1) + (E)-4-((2R,4R,6S)-4-Benzyloxy-6-methoxy-3,3-dimethyl-tetrahydro-pyran-2-yl)-but-2-enenitrile (253800-08-7) → 2-[(E)-3-((2R,4R,6S)-4-Benzyloxy-6-methoxy-3,3-dimethyl-tetrahydro-pyran-2-yl)-propenyl]-5-methoxy-oxazole-4-carboxylic acid methyl ester (253800-09-8)

Guidance literature:

dirhodium tetraacetate; In chloroform; for 15h; Heating;

DOI:10.1055/s-1999-2922

Reference yield:

((2R,4R,6S)-4-Benzyloxy-6-methoxy-3,3-dimethyl-tetrahydro-pyran-2-yl)-acetaldehyde → 2-[(E)-3-((2R,4R,6S)-4-Benzyloxy-6-methoxy-3,3-dimethyl-tetrahydro-pyran-2-yl)-propenyl]-5-methoxy-oxazole-4-carboxylic acid methyl ester (253800-09-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / LiCl / toluene / 18 h / 20 °C

2: 65 percent / Rh₂(OAc)4 / CHCl₃ / 15 h / Heating

With lithium chloride; dirhodium tetraacetate; In chloroform; toluene; 1: Condensation / 2: Cycloaddition;

DOI:10.1055/s-1999-2922

Reference yield: 45.0%

2-[(E)-3-((2R,4R,6S)-4-Benzyloxy-6-methoxy-3,3-dimethyl-tetrahydro-pyran-2-yl)-propenyl]-5-methoxy-oxazole-4-carboxylic acid methyl ester (253800-09-8) → {2-[(E)-3-((2R,4R,6S)-4-Benzyloxy-6-methoxy-3,3-dimethyl-tetrahydro-pyran-2-yl)-propenyl]-oxazol-4-yl}-methanol

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -78 ℃; for 3h;

DOI:10.1055/s-1999-2922

upstream raw materials:

dimethyl diazomalonate

(E)-4-((2R,4R,6S)-4-Benzyloxy-6-methoxy-3,3-dimethyl-tetrahydro-pyran-2-yl)-but-2-enenitrile

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