penta-N-acetyldibekacin

Base Information

• Chemical Name: penta-N-acetyldibekacin
• CAS No.: 108050-24-4
• Molecular Formula: C₂₈H₄₇N₅O₁₃
• Molecular Weight: 661.707
• Mol file: 108050-24-4.mol

Synonyms:penta-N-acetyldibekacin

Chemical Property of penta-N-acetyldibekacin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of penta-N-acetyldibekacin

There total 15 articles about penta-N-acetyldibekacin 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:

N-[(1R,2S,3S,4R,5S)-5-Acetylamino-4-[(2R,3R,6S)-3-acetylamino-6-(acetylamino-methyl)-tetrahydro-pyran-2-yloxy]-2-((2S,3R,4S,5S,6R)-4-acetylamino-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-hydroxy-cyclohexyl]-acetamide → penta-N-acetyldibekacin (108050-24-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In acetic acid; under 1900 Torr; Yield given;

DOI:10.1248/cpb.35.2136

Reference yield:

N-[(2S,5R,6R)-5-Amino-6-((3aS,4R,5S,7R,7aS)-5,7-diamino-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yloxy)-tetrahydro-pyran-2-ylmethyl]-acetamide → penta-N-acetyldibekacin (108050-24-4)

Guidance literature:

Multi-step reaction with 6 steps

1: Na₂CO₃ / H₂O; dioxane

2: 80 percent aq. AcOH / 60 °C

3: 77 percent / AgClO₄, sym-collidine / benzene; dioxane / 0.5 h / 24 °C

4: 1.) Dowex 1*2(OH- form); 2.) Ba(OH)2*8H₂O / 1.) acetone, H₂O; 2.) dioxane, H₂O

5: methanol

6: H₂ / 5 percent Pd/C / acetic acid / 1900 Torr

With 2,4,6-trimethyl-pyridine; barium dihydroxide; Dowex 1*2(OH- form); hydrogen; silver perchlorate; sodium carbonate; acetic acid; palladium on activated charcoal; In 1,4-dioxane; methanol; water; acetic acid; benzene;

DOI:10.1248/cpb.35.2136

Reference yield:

(2R,3S,4S,5R,6R)-4-(2,4-Dinitro-phenylamino)-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3,5-diol → penta-N-acetyldibekacin (108050-24-4)

Guidance literature:

Multi-step reaction with 7 steps

1: BaO, Ba(OH)2*8H₂O / dimethylformamide

2: 6 N aq. HCl, AcOH / 90 °C

3: 25 percent HBr / CHCl₃ / 5 °C

4: 77 percent / AgClO₄, sym-collidine / benzene; dioxane / 0.5 h / 24 °C

5: 1.) Dowex 1*2(OH- form); 2.) Ba(OH)2*8H₂O / 1.) acetone, H₂O; 2.) dioxane, H₂O

6: methanol

7: H₂ / 5 percent Pd/C / acetic acid / 1900 Torr

With 2,4,6-trimethyl-pyridine; hydrogenchloride; barium dihydroxide; Dowex 1*2(OH- form); hydrogen bromide; hydrogen; silver perchlorate; acetic acid; barium(II) oxide; palladium on activated charcoal; In 1,4-dioxane; methanol; chloroform; acetic acid; N,N-dimethyl-formamide; benzene;

DOI:10.1248/cpb.35.2136

upstream raw materials:

{(1R,2S,3R,4R,5S)-4-[(2R,3R,6S)-6-(Acetylamino-methyl)-3-ethoxycarbonylamino-tetrahydro-pyran-2-yloxy]-5-ethoxycarbonylamino-2,3-dihydroxy-cyclohexyl}-carbamic acid ethyl ester

((2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-bromo-tetrahydro-pyran-4-yl)-(2,4-dinitro-phenyl)-amine

(3R,4S,5S,6R)-3,5-Bis-benzyloxy-6-benzyloxymethyl-4-(2,4-dinitro-phenylamino)-tetrahydro-pyran-2-ol

Acetic acid (4R,6S,7R,7aS)-7-[(2R,3R,6S)-6-(acetylamino-methyl)-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy]-6-benzyloxycarbonylamino-2,2-dimethyl-4-nitro-hexahydro-benzo[1,3]dioxol-5-yl ester

Downstream raw materials:

dibecacin

Refernces