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

Base Information

• Chemical Name: (E)-4-((2R,4R,6S)-4-Benzyloxy-6-methoxy-3,3-dimethyl-tetrahydro-pyran-2-yl)-but-2-enenitrile
• CAS No.: 253800-08-7
• Molecular Formula: C₁₉H₂₅NO₃
• Molecular Weight: 315.412
• Mol file: 253800-08-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (E)-4-((2R,4R,6S)-4-Benzyloxy-6-methoxy-3,3-dimethyl-tetrahydro-pyran-2-yl)-but-2-enenitrile 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: 94.0%

cyanomethylene triphenylphosphorane (16640-68-9) + ((2R,4R,6S)-4-Benzyloxy-6-methoxy-3,3-dimethyl-tetrahydro-pyran-2-yl)-acetaldehyde → (E)-4-((2R,4R,6S)-4-Benzyloxy-6-methoxy-3,3-dimethyl-tetrahydro-pyran-2-yl)-but-2-enenitrile (253800-08-7)

Guidance literature:

With lithium chloride; In toluene; at 20 ℃; for 18h;

DOI:10.1055/s-1999-2922

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:

(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]-oxazol-4-yl}-methanol

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / Rh₂(OAc)4 / CHCl₃ / 15 h / Heating

2: 45 percent / LiAlH₄ / tetrahydrofuran / 3 h / -78 °C

With lithium aluminium tetrahydride; dirhodium tetraacetate; In tetrahydrofuran; chloroform; 1: Cycloaddition / 2: Reduction;

DOI:10.1055/s-1999-2922

upstream raw materials:

cyanomethylene triphenylphosphorane

Downstream raw materials:

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