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-((2S,3R,4R,5R)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yloxy)-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-((2S,3R,4R,5R)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yloxy)-cyclohexyl ester
• CAS No.: 289505-15-3
• Molecular Formula: C₃₁H₄₁N₉O₁₈
• Molecular Weight: 827.716

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-((2S,3R,4R,5R)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yloxy)-cyclohexyl ester

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-((2S,3R,4R,5R)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yloxy)-cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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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-((2S,3R,4R,5R)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yloxy)-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-((2S,3R,4R,5R)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yloxy)-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:

Paromamine (534-47-4,11030-86-7) → 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-((2S,3R,4R,5R)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yloxy)-cyclohexyl ester (289505-15-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 65 percent / TfN₃; K₂CO₃ / methanol; H₂O / 24 h

2: 75 percent / pyridine / 4 h / -10 °C

3: 95 percent / pyridine / 1 h / 0 °C

4: TMSOTf; molecular sieves / CH₂Cl₂ / 10 h

With pyridine; molecular sieve; trimethylsilyl trifluoromethanesulfonate; triflic azide; potassium carbonate; In methanol; dichloromethane; water; 1: azidation / 2: Acetylation / 3: Acetylation / 4: Substitution;

DOI:10.1016/S0040-4039(00)00586-4

Reference yield:

paromomycin (7542-37-2,1390-73-4) → 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-((2S,3R,4R,5R)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yloxy)-cyclohexyl ester (289505-15-3)

Guidance literature:

Multi-step reaction with 5 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

4: 95 percent / pyridine / 1 h / 0 °C

5: TMSOTf; molecular sieves / CH₂Cl₂ / 10 h

With pyridine; hydrogenchloride; molecular sieve; trimethylsilyl trifluoromethanesulfonate; triflic azide; potassium carbonate; In methanol; dichloromethane; water; 1: Hydrolysis / 2: azidation / 3: Acetylation / 4: Acetylation / 5: Substitution;

DOI:10.1016/S0040-4039(00)00586-4

Reference yield:

(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 (289505-10-8) → 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-((2S,3R,4R,5R)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yloxy)-cyclohexyl ester (289505-15-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / pyridine / 4 h / -10 °C

2: 95 percent / pyridine / 1 h / 0 °C

3: TMSOTf; molecular sieves / CH₂Cl₂ / 10 h

With pyridine; molecular sieve; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; 1: Acetylation / 2: Acetylation / 3: Substitution;

DOI:10.1016/S0040-4039(00)00586-4

upstream raw materials:

Paromamine

paromomycin

(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

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

Downstream raw materials:

6'-hydroxyl-ribostamycin

(2R,3S,4R,5R,6S)-5-Azido-6-[(1R,2R,3S,4R,6S)-4,6-diazido-2-((2S,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yloxy)-3-hydroxy-cyclohexyloxy]-2-hydroxymethyl-tetrahydro-pyran-3,4-diol

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