(2S,3S,4R,6S)-3-Benzyloxy-6-ethoxy-4-methoxy-2,4-dimethyl-tetrahydro-pyran

Base Information

• Chemical Name: (2S,3S,4R,6S)-3-Benzyloxy-6-ethoxy-4-methoxy-2,4-dimethyl-tetrahydro-pyran
• CAS No.: 153029-79-9
• Molecular Formula: C₁₇H₂₆O₄
• Molecular Weight: 294.391

Synonyms:(2S,3S,4R,6S)-3-Benzyloxy-6-ethoxy-4-methoxy-2,4-dimethyl-tetrahydro-pyran

Chemical Property of (2S,3S,4R,6S)-3-Benzyloxy-6-ethoxy-4-methoxy-2,4-dimethyl-tetrahydro-pyran

Chemical Property:

Purity/Quality:

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Technology Process of (2S,3S,4R,6S)-3-Benzyloxy-6-ethoxy-4-methoxy-2,4-dimethyl-tetrahydro-pyran

There total 2 articles about (2S,3S,4R,6S)-3-Benzyloxy-6-ethoxy-4-methoxy-2,4-dimethyl-tetrahydro-pyran 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: 92.0%

benzyl bromide (100-39-0) + (2S,3S,4R,6S)-6-Ethoxy-4-methoxy-2,4-dimethyl-tetrahydro-pyran-3-ol (153029-63-1) → (2S,3S,4R,6S)-3-Benzyloxy-6-ethoxy-4-methoxy-2,4-dimethyl-tetrahydro-pyran (153029-79-9)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.7164/antibiotics.49.582

Reference yield:

erythromycin (114-07-8) → (2S,3S,4R,6S)-3-Benzyloxy-6-ethoxy-4-methoxy-2,4-dimethyl-tetrahydro-pyran (153029-79-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / p-TsOH / acetonitrile / 1 h / Ambient temperature

2: 92 percent / NaH / dimethylformamide / Ambient temperature

With sodium hydride; toluene-4-sulfonic acid; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.7164/antibiotics.49.582

Reference yield:

(2S,3S,4R,6S)-3-Benzyloxy-6-ethoxy-4-methoxy-2,4-dimethyl-tetrahydro-pyran (153029-79-9) → (4R,5S,6S)-5-Benzyloxy-4-methoxy-4,6-dimethyl-tetrahydro-pyran-2-ol

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 30 ℃;

DOI:10.7164/antibiotics.49.582

upstream raw materials:

benzyl bromide

(2S,3S,4R,6S)-6-Ethoxy-4-methoxy-2,4-dimethyl-tetrahydro-pyran-3-ol

erythromycin

Downstream raw materials:

2-((4R,5S,6S)-5-Benzyloxy-4-methoxy-4,6-dimethyl-tetrahydro-pyran-2-ylsulfanyl)-pyridine

C₄₆H₆₉NO₁₄

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