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

Base Information

• Chemical Name: {(1R,2S,3R,4R,5S)-5-tert-Butoxycarbonylamino-4-[(2R,3R,4R,5S,6R)-3-tert-butoxycarbonylamino-6-(tert-butoxycarbonylamino-methyl)-4,5-dihydroxy-tetrahydro-pyran-2-yloxy]-2,3-dihydroxy-cyclohexyl}-carbamic acid tert-butyl ester
• CAS No.: 54230-72-7
• Molecular Formula: C₃₂H₅₈N₄O₁₄
• Molecular Weight: 722.831
• Mol file: 54230-72-7.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about {(1R,2S,3R,4R,5S)-5-tert-Butoxycarbonylamino-4-[(2R,3R,4R,5S,6R)-3-tert-butoxycarbonylamino-6-(tert-butoxycarbonylamino-methyl)-4,5-dihydroxy-tetrahydro-pyran-2-yloxy]-2,3-dihydroxy-cyclohexyl}-carbamic acid tert-butyl 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: 83.0%

di-tert-butyl dicarbonate (24424-99-5) + neamine tetrahydrochloride (15446-43-2) → {(1R,2S,3R,4R,5S)-5-tert-Butoxycarbonylamino-4-[(2R,3R,4R,5S,6R)-3-tert-butoxycarbonylamino-6-(tert-butoxycarbonylamino-methyl)-4,5-dihydroxy-tetrahydro-pyran-2-yloxy]-2,3-dihydroxy-cyclohexyl}-carbamic acid tert-butyl ester (54230-72-7)

Guidance literature:

With triethylamine;

DOI:10.1021/jo000589k

Reference yield:

{(1R,2S,3R,4R,5S)-5-tert-Butoxycarbonylamino-4-[(2R,3R,4R,5S,6R)-3-tert-butoxycarbonylamino-6-(tert-butoxycarbonylamino-methyl)-4,5-dihydroxy-tetrahydro-pyran-2-yloxy]-2,3-dihydroxy-cyclohexyl}-carbamic acid tert-butyl ester (54230-72-7) → 1,3,2',6'-tetra-N-benzyl-3'-O-(5''-bromopentyl)-1,3,2'-tri-N-tert-butoxycarbonyl-6'-N,4'-O-carbonyl-5,6-O-cyclohexylideneneamine (312957-57-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 69 percent

2.1: 74 percent / imidazole / dimethylformamide / 20 °C

3.1: NaH / dimethylformamide / 2 h / 20 °C

3.2: 79 percent / dimethylformamide / 6 h / 20 °C

4.1: 66 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.17 h

5.1: 92 percent / KOH / dimethylsulfoxide / 0.5 h / 20 °C

With 1H-imidazole; potassium hydroxide; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jo000589k

Reference yield:

{(1R,2S,3R,4R,5S)-5-tert-Butoxycarbonylamino-4-[(2R,3R,4R,5S,6R)-3-tert-butoxycarbonylamino-6-(tert-butoxycarbonylamino-methyl)-4,5-dihydroxy-tetrahydro-pyran-2-yloxy]-2,3-dihydroxy-cyclohexyl}-carbamic acid tert-butyl ester (54230-72-7) → 1,3,2',6'-tetra-N-benzyl-3'-O-(6''-bromohexyl)-1,3,2'-tri-N-tert-butoxycarbonyl-6'-N,4'-O-carbonyl-5,6-O-cyclohexylideneneamine (312957-58-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 69 percent

2.1: 74 percent / imidazole / dimethylformamide / 20 °C

3.1: NaH / dimethylformamide / 2 h / 20 °C

3.2: 79 percent / dimethylformamide / 6 h / 20 °C

4.1: 66 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.17 h

5.1: 91 percent / KOH / dimethylsulfoxide / 0.5 h / 20 °C

With 1H-imidazole; potassium hydroxide; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jo000589k

upstream raw materials:

di-tert-butyl dicarbonate

neamine tetrahydrochloride

Downstream raw materials:

1,3,2',6'-tetra-N-benzyl-1,3,2'-tri-N-tert-butoxycarbonyl-6'-N,4'-O-carbonyl-5,6-O-cyclohexylideneneamine

1,3,2',6'-tetra-N-benzyl-1,3,2'-tri-N-tert-butoxycarbonyl-3'-O-tert-butyldimethylsilyl-6'-N,4'-O-carbonyl-5,6-O-cyclohexylideneneamine

1,3,2',6'-tetra-N-benzyl-3'-O-(5''-bromopentyl)-1,3,2'-tri-N-tert-butoxycarbonyl-6'-N,4'-O-carbonyl-5,6-O-cyclohexylideneneamine

1,3,2',6'-tetra-N-benzyl-3'-O-(6''-bromohexyl)-1,3,2'-tri-N-tert-butoxycarbonyl-6'-N,4'-O-carbonyl-5,6-O-cyclohexylideneneamine