Acetic acid (1S,2S,3R,4S,6R)-4,6-diazido-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-2-hydroxy-cyclohexyl ester

Base Information

Chemical Name:Acetic acid (1S,2S,3R,4S,6R)-4,6-diazido-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-2-hydroxy-cyclohexyl ester
CAS No.:289505-11-9
Molecular Formula:C₂₀H₂₇N₉O₁₁
Molecular Weight:569.488
Hs Code.:

Acetic acid (1S,2S,3R,4S,6R)-4,6-diazido-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-2-hydroxy-cyclohexyl ester

Synonyms:Acetic acid (1S,2S,3R,4S,6R)-4,6-diazido-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-2-hydroxy-cyclohexyl ester

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Chemical Property of Acetic acid (1S,2S,3R,4S,6R)-4,6-diazido-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-2-hydroxy-cyclohexyl ester

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Technology Process of Acetic acid (1S,2S,3R,4S,6R)-4,6-diazido-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-2-hydroxy-cyclohexyl ester

There total 4 articles about Acetic acid (1S,2S,3R,4S,6R)-4,6-diazido-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-2-hydroxy-cyclohexyl ester 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: 75.0%

: 108-24-7
acetic anhydride

: 289505-10-8
(2R,3S,4R,5R,6S)-5-azido-6-(((1R,2R,3S,4R,6S)-4, 6-diazido-2,3-dihydroxycyclohexyl)oxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol

: 289505-11-9
Acetic acid (1S,2S,3R,4S,6R)-4,6-diazido-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-2-hydroxy-cyclohexyl ester

Guidance literature:: With pyridine; at -10 ℃; for 4h;
DOI:10.1016/S0040-4039(00)00586-4

Reference yield:

: 534-47-4,11030-86-7
Paromamine

: 289505-11-9
Acetic acid (1S,2S,3R,4S,6R)-4,6-diazido-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-2-hydroxy-cyclohexyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 90 percent / trifluoromethanesulfonyl azide; Et₃N; CuSO₄ / CH₂Cl₂; methanol; H₂O

2: 65 percent / pyridine / -6 °C

With pyridine; triflic azide; copper(II) sulfate; triethylamine; In methanol; dichloromethane; water;
DOI:10.1016/j.bmcl.2006.09.013

Reference yield:

: 7542-37-2,1390-73-4
paromomycin

: 289505-11-9
Acetic acid (1S,2S,3R,4S,6R)-4,6-diazido-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-2-hydroxy-cyclohexyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 65 percent / HCl / methanol / 10 h / 70 °C

2: 65 percent / TfN₃; K₂CO₃ / methanol; H₂O / 24 h

3: 75 percent / pyridine / 4 h / -10 °C

With pyridine; hydrogenchloride; triflic azide; potassium carbonate; In methanol; water; 1: Hydrolysis / 2: azidation / 3: Acetylation;
DOI:10.1016/S0040-4039(00)00586-4