((2R,3S,6S)-3-acetoxy-6-(1-benzyl-1H-1,2,3-triazol-4-yl)-3,6-dihydro-2H-pyran-2-yl)methyl acetate

Base Information

• Chemical Name: ((2R,3S,6S)-3-acetoxy-6-(1-benzyl-1H-1,2,3-triazol-4-yl)-3,6-dihydro-2H-pyran-2-yl)methyl acetate
• CAS No.: 1366497-37-1
• Molecular Formula: C₁₉H₂₁N₃O₅
• Molecular Weight: 371.393

Synonyms:((2R,3S,6S)-3-acetoxy-6-(1-benzyl-1H-1,2,3-triazol-4-yl)-3,6-dihydro-2H-pyran-2-yl)methyl acetate

Chemical Property of ((2R,3S,6S)-3-acetoxy-6-(1-benzyl-1H-1,2,3-triazol-4-yl)-3,6-dihydro-2H-pyran-2-yl)methyl acetate

Chemical Property:

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Technology Process of ((2R,3S,6S)-3-acetoxy-6-(1-benzyl-1H-1,2,3-triazol-4-yl)-3,6-dihydro-2H-pyran-2-yl)methyl acetate

There total 2 articles about ((2R,3S,6S)-3-acetoxy-6-(1-benzyl-1H-1,2,3-triazol-4-yl)-3,6-dihydro-2H-pyran-2-yl)methyl 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: 74.0%

((2R,3S,6S)-3-acetoxy-6-((trimethylsilyl)ethynyl)-3,6-dihydro-2H-pyran-2-yl)methyl acetate (115029-76-0) + benzyl azide (622-79-7) → ((2R,3S,6S)-3-acetoxy-6-(1-benzyl-1H-1,2,3-triazol-4-yl)-3,6-dihydro-2H-pyran-2-yl)methyl acetate (1366497-37-1)

Guidance literature:

With copper(l) iodide; tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h; Sonication; Inert atmosphere;

DOI:10.1016/j.tetlet.2012.01.102

Reference yield:

D-glucal triacetate (2873-29-2) → ((2R,3S,6S)-3-acetoxy-6-(1-benzyl-1H-1,2,3-triazol-4-yl)-3,6-dihydro-2H-pyran-2-yl)methyl acetate (1366497-37-1)

Guidance literature:

Multi-step reaction with 2 steps

1: boron trifluoride diethyl etherate / acetonitrile / 0.25 h / 0 °C / Inert atmosphere

2: copper(l) iodide; tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Sonication; Inert atmosphere

With copper(l) iodide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; In tetrahydrofuran; acetonitrile;

DOI:10.1016/j.tetlet.2012.01.102

Reference yield: 94.0%

((2R,3S,6S)-3-acetoxy-6-(1-benzyl-1H-1,2,3-triazol-4-yl)-3,6-dihydro-2H-pyran-2-yl)methyl acetate (1366497-37-1) → (2R,3S,6S)-6-(1-benzyl-1H-1,2,3-triazol-4-yl)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol (1366497-60-0)

Guidance literature:

With water; potassium carbonate; In methanol; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.tetlet.2012.01.102

upstream raw materials:

((2R,3S,6S)-3-acetoxy-6-((trimethylsilyl)ethynyl)-3,6-dihydro-2H-pyran-2-yl)methyl acetate

benzyl azide

D-glucal triacetate

Downstream raw materials:

(2R,3S,6S)-6-(1-benzyl-1H-1,2,3-triazol-4-yl)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol

(2S,3S,6S)-6-(1-phenyl-1H-1,2,3-triazol-4-yl)-2-(phenylselanylmethyl)-3,6-dihydro-2H-pyran-3-ol

(2S,3S,6S)-6-(1-phenyl-1H-1,2,3-triazol-4-yl)-2-((((3aR,5S,5aR,8aS,8bR)-2,2,7,7-tetramethyltetrahydro-3ah-bis[1,3]dioxolo[4,5-b:4',5'-d]pyran-5-yl)methylselanyl)methyl)-3,6-dihydro-2H-pyran-3-ol

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