(1S,2S,3R,6S)-4-(acetoxymethyl)-6-[4-(4-methylphenyl)-1H-1,2,3-triazol-1-yl]cyclohex-4-ene-1,2,3-triyl triacetate

Base Information

• Chemical Name: (1S,2S,3R,6S)-4-(acetoxymethyl)-6-[4-(4-methylphenyl)-1H-1,2,3-triazol-1-yl]cyclohex-4-ene-1,2,3-triyl triacetate
• CAS No.: 1618635-65-6
• Molecular Formula: C₂₄H₂₇N₃O₈
• Molecular Weight: 485.494

Synonyms:(1S,2S,3R,6S)-4-(acetoxymethyl)-6-[4-(4-methylphenyl)-1H-1,2,3-triazol-1-yl]cyclohex-4-ene-1,2,3-triyl triacetate

Chemical Property of (1S,2S,3R,6S)-4-(acetoxymethyl)-6-[4-(4-methylphenyl)-1H-1,2,3-triazol-1-yl]cyclohex-4-ene-1,2,3-triyl triacetate

Chemical Property:

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Technology Process of (1S,2S,3R,6S)-4-(acetoxymethyl)-6-[4-(4-methylphenyl)-1H-1,2,3-triazol-1-yl]cyclohex-4-ene-1,2,3-triyl triacetate

There total 5 articles about (1S,2S,3R,6S)-4-(acetoxymethyl)-6-[4-(4-methylphenyl)-1H-1,2,3-triazol-1-yl]cyclohex-4-ene-1,2,3-triyl triacetate 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: 93.0%

(1S)-(1,3,6/2)-4-acetoxymethyl-1,2,3-tri-O-acetyl-6-azido-4-cyclohexene-1,2,3-triol (90025-03-9) + 4-n-methylphenylacetylene (766-97-2) → (1S,2S,3R,6S)-4-(acetoxymethyl)-6-[4-(4-methylphenyl)-1H-1,2,3-triazol-1-yl]cyclohex-4-ene-1,2,3-triyl triacetate (1618635-65-6)

Guidance literature:

With copper(l) iodide; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 100 ℃; for 6h; Inert atmosphere;

DOI:10.1002/ejoc.201301874

Reference yield:

valienamine (38231-86-6) → (1S,2S,3R,6S)-4-(acetoxymethyl)-6-[4-(4-methylphenyl)-1H-1,2,3-triazol-1-yl]cyclohex-4-ene-1,2,3-triyl triacetate (1618635-65-6)

Guidance literature:

Multi-step reaction with 3 steps

1: imidazole-1-sulfonyl azide hydrochloride; potassium carbonate; copper(ll) sulfate pentahydrate / methanol / 12 h / 20 °C

2: sodium L-ascorbate / N,N-dimethyl-formamide / 8 h / 100 °C / Inert atmosphere

3: dmap / N,N-dimethyl-formamide / 6 h / Inert atmosphere

With dmap; imidazole-1-sulfonyl azide hydrochloride; copper(ll) sulfate pentahydrate; potassium carbonate; sodium L-ascorbate; In methanol; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201301874

Reference yield:

(1S,2S,3R,6S)-6-Azido-4-hydroxymethyl-cyclohex-4-ene-1,2,3-triol → (1S,2S,3R,6S)-4-(acetoxymethyl)-6-[4-(4-methylphenyl)-1H-1,2,3-triazol-1-yl]cyclohex-4-ene-1,2,3-triyl triacetate (1618635-65-6)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 20 °C

2: copper(l) iodide; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 6 h / 100 °C / Inert atmosphere

With copper(l) iodide; N-ethyl-N,N-diisopropylamine; In pyridine; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201301874

upstream raw materials:

acetic anhydride

4-n-methylphenylacetylene

(1S)-(1,3,6/2)-4-acetoxymethyl-1,2,3-tri-O-acetyl-6-azido-4-cyclohexene-1,2,3-triol

valienamine

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