(+)-2,3,4,5,6-penta-O-acetyl-1-deoxy-1-azido-myo-inositol

Base Information

• Chemical Name: (+)-2,3,4,5,6-penta-O-acetyl-1-deoxy-1-azido-myo-inositol
• CAS No.: 639799-31-8
• Molecular Formula: C₁₆H₂₁N₃O₁₀
• Molecular Weight: 415.357
• Mol file: 639799-31-8.mol

Synonyms:(+)-2,3,4,5,6-penta-O-acetyl-1-deoxy-1-azido-myo-inositol

Chemical Property of (+)-2,3,4,5,6-penta-O-acetyl-1-deoxy-1-azido-myo-inositol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-2,3,4,5,6-penta-O-acetyl-1-deoxy-1-azido-myo-inositol

There total 7 articles about (+)-2,3,4,5,6-penta-O-acetyl-1-deoxy-1-azido-myo-inositol 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:

(-)-2,3-dibromocyclohex-5-ene-1,4-diol (169529-93-5) → (+)-2,3,4,5,6-penta-O-acetyl-1-deoxy-1-azido-myo-inositol (639799-31-8,6730-18-3)

Guidance literature:

Multi-step reaction with 7 steps

1: LiOH / methanol; diethyl ether / 2 h / 0 °C

2: aq. NaN₃; NH₄Cl / 1,2-dimethoxy-ethane; ethanol / 3 h / 0 °C

3: LiOH / diethyl ether; methanol / 2 h / 10 °C

4: aq. p-TsOH / 48 h / 20 °C

5: 96 percent / pyridine / 12 h / 20 °C

6: aq. NaIO₄; RuCl₃ / acetonitrile / ice-cooling

7: pyridine / 12 h

With pyridine; ruthenium trichloride; lithium hydroxide; sodium periodate; sodium azide; ammonium chloride; toluene-4-sulfonic acid; In methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; acetonitrile;

DOI:10.1039/b302622a

Reference yield:

(1S,2R,3S,6S)-2-bromo-7-oxabicyclo[4.1.0]hept-4-en-3-ol (80582-73-6) → (+)-2,3,4,5,6-penta-O-acetyl-1-deoxy-1-azido-myo-inositol (639799-31-8,6730-18-3)

Guidance literature:

Multi-step reaction with 6 steps

1: aq. NaN₃; NH₄Cl / 1,2-dimethoxy-ethane; ethanol / 3 h / 0 °C

2: LiOH / diethyl ether; methanol / 2 h / 10 °C

3: aq. p-TsOH / 48 h / 20 °C

4: 96 percent / pyridine / 12 h / 20 °C

5: aq. NaIO₄; RuCl₃ / acetonitrile / ice-cooling

6: pyridine / 12 h

With pyridine; ruthenium trichloride; lithium hydroxide; sodium periodate; sodium azide; ammonium chloride; toluene-4-sulfonic acid; In methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; acetonitrile;

DOI:10.1039/b302622a

Reference yield:

(1S,2R,3S,6R)-6-azido-2-bromocyclohex-4-ene-1,3-diol (251538-17-7) → (+)-2,3,4,5,6-penta-O-acetyl-1-deoxy-1-azido-myo-inositol (639799-31-8,6730-18-3)

Guidance literature:

Multi-step reaction with 5 steps

1: LiOH / diethyl ether; methanol / 2 h / 10 °C

2: aq. p-TsOH / 48 h / 20 °C

3: 96 percent / pyridine / 12 h / 20 °C

4: aq. NaIO₄; RuCl₃ / acetonitrile / ice-cooling

5: pyridine / 12 h

With pyridine; ruthenium trichloride; lithium hydroxide; sodium periodate; toluene-4-sulfonic acid; In methanol; diethyl ether; acetonitrile;

DOI:10.1039/b302622a

upstream raw materials:

acetic anhydride

(-)-4,5,6-tri-O-acetyl-1-azido-myo-inositol

(-)-2,3-dibromocyclohex-5-ene-1,4-diol

(1S,2R,3S,6S)-2-bromo-7-oxabicyclo[4.1.0]hept-4-en-3-ol

Downstream raw materials:

N-acetyl-myo-inosamine

1D-penta-O-acetyl-1-acetylamino-1-deoxy-myo-inositol

Refernces