(2R,3S,4R,5R,6R)-5-Amino-6-((1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxy-cyclohexyloxy)-2-[(trityl-amino)-methyl]-tetrahydro-pyran-3,4-diol

Base Information

• Chemical Name: (2R,3S,4R,5R,6R)-5-Amino-6-((1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxy-cyclohexyloxy)-2-[(trityl-amino)-methyl]-tetrahydro-pyran-3,4-diol
• CAS No.: 260786-20-7
• Molecular Formula: C₃₁H₄₀N₄O₆
• Molecular Weight: 564.682
• Mol file: 260786-20-7.mol

Synonyms:(2R,3S,4R,5R,6R)-5-Amino-6-((1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxy-cyclohexyloxy)-2-[(trityl-amino)-methyl]-tetrahydro-pyran-3,4-diol

Chemical Property of (2R,3S,4R,5R,6R)-5-Amino-6-((1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxy-cyclohexyloxy)-2-[(trityl-amino)-methyl]-tetrahydro-pyran-3,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R,5R,6R)-5-Amino-6-((1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxy-cyclohexyloxy)-2-[(trityl-amino)-methyl]-tetrahydro-pyran-3,4-diol

There total 2 articles about (2R,3S,4R,5R,6R)-5-Amino-6-((1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxy-cyclohexyloxy)-2-[(trityl-amino)-methyl]-tetrahydro-pyran-3,4-diol 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: 52.0%

neomycin A (3947-65-7) + trityl chloride (76-83-5) → (2R,3S,4R,5R,6R)-5-Amino-6-((1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxy-cyclohexyloxy)-2-[(trityl-amino)-methyl]-tetrahydro-pyran-3,4-diol (260786-20-7)

Guidance literature:

With triethylamine; In 1,4-dioxane; methanol; at 20 ℃; for 18h;

DOI:10.1016/S0040-4039(99)01978-4

Reference yield:

neomycin B (119-04-0) → (2R,3S,4R,5R,6R)-5-Amino-6-((1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxy-cyclohexyloxy)-2-[(trityl-amino)-methyl]-tetrahydro-pyran-3,4-diol (260786-20-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: MeOH; HCl / 16 h

1.2: 67 percent / Amberlite IRA-400 (OH^-) / aq. methanol / 0.5 h

2.1: 52 percent / Et₃N / aq. methanol; dioxane / 18 h / 20 °C

With hydrogenchloride; methanol; triethylamine; In 1,4-dioxane; methanol; 1.1: acidic methanolysis / 1.2: Hydrolysis / 2.1: Alkylation;

DOI:10.1016/S0040-4039(99)01978-4

Reference yield: 63.0%

di-tert-butyl dicarbonate (24424-99-5) + (2R,3S,4R,5R,6R)-5-Amino-6-((1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxy-cyclohexyloxy)-2-[(trityl-amino)-methyl]-tetrahydro-pyran-3,4-diol (260786-20-7) → ((1R,2S,3R,4R,5S)-5-tert-Butoxycarbonylamino-4-{(2R,3R,4R,5S,6R)-3-tert-butoxycarbonylamino-4,5-dihydroxy-6-[(trityl-amino)-methyl]-tetrahydro-pyran-2-yloxy}-2,3-dihydroxy-cyclohexyl)-carbamic acid tert-butyl ester (260786-21-8)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; at 20 ℃; for 18h;

DOI:10.1016/S0040-4039(99)01978-4

upstream raw materials:

neomycin A

trityl chloride

neomycin B

Downstream raw materials:

((1R,2S,3R,4R,5S)-5-tert-Butoxycarbonylamino-4-{(2R,3R,4R,5S,6R)-3-tert-butoxycarbonylamino-4,5-dihydroxy-6-[(trityl-amino)-methyl]-tetrahydro-pyran-2-yloxy}-2,3-dihydroxy-cyclohexyl)-carbamic acid tert-butyl ester

((1R,2S,3R,4R,5S)-5-Benzyloxycarbonylamino-4-{(2R,3R,4R,5S,6R)-3-benzyloxycarbonylamino-4,5-dihydroxy-6-[(trityl-amino)-methyl]-tetrahydro-pyran-2-yloxy}-2,3-dihydroxy-cyclohexyl)-carbamic acid benzyl ester

1,3,2'-tri-N-(tert-butoxycarbonyl)neamine