(1S,2R,3S,4S,6S)-4-(acetoxymethyl)-6-azido-4-hydroxycyclohexane-1,2,3-triyl triacetate

Base Information

• Chemical Name: (1S,2R,3S,4S,6S)-4-(acetoxymethyl)-6-azido-4-hydroxycyclohexane-1,2,3-triyl triacetate
• CAS No.: 148347-73-3
• Molecular Formula: C₁₅H₂₁N₃O₉
• Molecular Weight: 387.346

Synonyms:(1S,2R,3S,4S,6S)-4-(acetoxymethyl)-6-azido-4-hydroxycyclohexane-1,2,3-triyl triacetate

Chemical Property of (1S,2R,3S,4S,6S)-4-(acetoxymethyl)-6-azido-4-hydroxycyclohexane-1,2,3-triyl triacetate

Chemical Property:

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Technology Process of (1S,2R,3S,4S,6S)-4-(acetoxymethyl)-6-azido-4-hydroxycyclohexane-1,2,3-triyl triacetate

There total 17 articles about (1S,2R,3S,4S,6S)-4-(acetoxymethyl)-6-azido-4-hydroxycyclohexane-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: 54.0%

(1S)-(1,2,4/3,5)-2,3,4-triacetoxy-1-acetoxymethyl-5-bromocyclohexanol → 4,5,6-triacetoxy-1-(acetoxymethyl)cyclohex-2-enol + (1S,2R,3S,4S,6S)-4-(acetoxymethyl)-6-azido-4-hydroxycyclohexane-1,2,3-triyl triacetate (148347-73-3)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 90 ℃; for 95h;

Reference yield:

acetic anhydride (108-24-7) + (1S,2S,3R,4S,5S)-1-azido-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane (1054636-37-1) → (1S,2R,3S,4S,6S)-4-(acetoxymethyl)-6-azido-4-hydroxycyclohexane-1,2,3-triyl triacetate (148347-73-3)

Guidance literature:

In pyridine; dichloromethane; at 20 ℃; for 8h;

DOI:10.1002/ejoc.201301874

Reference yield:

C11H17N3O7 + acetic anhydride (108-24-7) → (1S,2R,3S,4S,6S)-4-(acetoxymethyl)-6-azido-4-hydroxycyclohexane-1,2,3-triyl triacetate (148347-73-3)

Guidance literature:

With dmap; triethylamine; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1002/ejoc.201300804

upstream raw materials:

(1R)-(-)-1,2,3-tri-O-acetyl-(1,3/2,4,6)-4-bromo-6-bromomethyl-1,2,3-cyclohexanetriol

(1R)-(1,3/2,4)-2,3,4-triacetoxy-1-bromo-5-methylenecyclohexane

(3S,4R,5R)-5-methanesulfonyloxy-3,4-dihydroxy-1-cyclohexene-1-carboxylic acid ethyl ester

(3S,4S,5S)-ethyl 5-azido-3,4-dihydroxycyclohex-1-ene-1-carboxylate

Downstream raw materials:

(1S,2S,3R,4S,5S)-1-amino-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane

(1S,2R,3S,4S,6S)-4-(acetoxymethyl)-4-hydroxy-6-(4-phenyl-1H-1,2,3-triazol-1-yl)cyclohexane-1,2,3-triyl triacetate

(1S,2R,3S,4S,6S)-4-(acetoxymethyl)-6-[4-(4-fluorophenyl)-1H-1,2,3-triazol-1-yl]-4-hydroxycyclohexane-1,2,3-triyl triacetate

(1S,2R,3S,4S,6S)-4-(acetoxymethyl)-4-hydroxy-6-[4-(4-nitrophenyl)-1H-1,2,3-triazol-1-yl]cyclohexane-1,2,3-triyl triacetate

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