methyl (2S,3S,4R,5S)-[5-benzyloxy-3,4-(cyclohexylidenedioxy)tetrahydropyran-2-yl]acetate

Base Information

• Chemical Name: methyl (2S,3S,4R,5S)-[5-benzyloxy-3,4-(cyclohexylidenedioxy)tetrahydropyran-2-yl]acetate
• CAS No.: 482636-02-2
• Molecular Formula: C₂₁H₂₈O₆
• Molecular Weight: 376.45

Synonyms:methyl (2S,3S,4R,5S)-[5-benzyloxy-3,4-(cyclohexylidenedioxy)tetrahydropyran-2-yl]acetate

Chemical Property of methyl (2S,3S,4R,5S)-[5-benzyloxy-3,4-(cyclohexylidenedioxy)tetrahydropyran-2-yl]acetate

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Technology Process of methyl (2S,3S,4R,5S)-[5-benzyloxy-3,4-(cyclohexylidenedioxy)tetrahydropyran-2-yl]acetate

There total 1 articles about methyl (2S,3S,4R,5S)-[5-benzyloxy-3,4-(cyclohexylidenedioxy)tetrahydropyran-2-yl]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: 97.0%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + methyl (2S,3R,4S,5S)-[5-benzyloxy-3,4-(dihydroxy)tetrahydropyran-2-yl]acetate (482635-99-4) → methyl (2S,3S,4R,5S)-[5-benzyloxy-3,4-(cyclohexylidenedioxy)tetrahydropyran-2-yl]acetate (482636-02-2)

Guidance literature:

With toluene-4-sulfonic acid; copper(II) sulfate; In benzene; at 20 ℃; for 1.5h;

DOI:10.1021/ol027192i

Reference yield: 93.0%

methyl (2S,3S,4R,5S)-[5-benzyloxy-3,4-(cyclohexylidenedioxy)tetrahydropyran-2-yl]acetate (482636-02-2) → (2S,3S,4R,5S)-[5-benzyloxy-3,4-(cyclohexylidenedioxy)tetrahydropyran-2-yl]-acetic acid (482636-03-3)

Guidance literature:

With potassium hydroxide; In methanol; water; at 20 ℃; for 0.5h;

DOI:10.1021/ol027192i

Reference yield: 91.0%

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + methyl (2S,3S,4R,5S)-[5-benzyloxy-3,4-(cyclohexylidenedioxy)tetrahydropyran-2-yl]acetate (482636-02-2) → (2S,3S,4R,5S)-[5-benzyloxy-3,4-(cyclohexylidenedioxy)tetrahydropyran-2-yl]-N-methoxy-N-methylacetamide (482636-05-5)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h;

DOI:10.1021/ol027192i

upstream raw materials:

cyclohexanone

methyl (2S,3R,4S,5S)-[5-benzyloxy-3,4-(dihydroxy)tetrahydropyran-2-yl]acetate

Downstream raw materials:

(2S,3S,4R,5S)-[5-benzyloxy-3,4-(cyclohexylidenedioxy)tetrahydropyran-2-yl]-N-methoxy-N-methylacetamide

(2S,3S,4R,5S)-[5-benzyloxy-3,4-(cyclohexylidenedioxy)tetrahydropyran-2-yl]-acetic acid

(2S,3S,4R,5S)-1-[5-benzyloxy-3,4-(cyclohexylidenedioxy)tetrahydropyran-2-yl]-propan-2-one

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