5-O-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6,3',4'-tri-O-acetyl-1,3,2',6'-tetraazidoneamine

Base Information

• Chemical Name: 5-O-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6,3',4'-tri-O-acetyl-1,3,2',6'-tetraazidoneamine
• CAS No.: 942420-67-9
• Molecular Formula: C₂₉H₃₈N₁₂O₁₆
• Molecular Weight: 810.692
• Mol file: 942420-67-9.mol

Synonyms:5-O-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6,3',4'-tri-O-acetyl-1,3,2',6'-tetraazidoneamine

Chemical Property of 5-O-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6,3',4'-tri-O-acetyl-1,3,2',6'-tetraazidoneamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-O-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6,3',4'-tri-O-acetyl-1,3,2',6'-tetraazidoneamine

There total 1 articles about 5-O-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6,3',4'-tri-O-acetyl-1,3,2',6'-tetraazidoneamine 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: 37.0%

phenyl 2,3,5-tri-O-acetyl-1-thio-β-D-ribofuranoside (52544-88-4) + 1,3,2′,6′-tetraazido-6,3′,4′-tri-O-acetylneamine (182554-04-7) → 5-O-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6,3',4'-tri-O-acetyl-1,3,2',6'-tetraazidoneamine (942420-67-9)

Guidance literature:

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at -50 - 20 ℃;

DOI:10.1021/jo062588j

Reference yield: 31.0%

5-O-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6,3',4'-tri-O-acetyl-1,3,2',6'-tetraazidoneamine (942420-67-9) + 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile (58632-95-4) → 5-O-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1-N-tert-butoxycarbonyl-6,3',4'-tri-O-acetyl-3,2',6'-triazidoneamine (942420-68-0)

Guidance literature:

With trimethylphosphane; In toluene; at -78 - 10 ℃;

DOI:10.1021/jo062588j

Reference yield:

5-O-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6,3',4'-tri-O-acetyl-1,3,2',6'-tetraazidoneamine (942420-67-9) → 5-O-(β-D-ribofuranosyl)-1-N-[(S)-4-amino-2-hydroxybutanoyl]neamine tetrahydrochloride

Guidance literature:

Multi-step reaction with 5 steps

1: 31 percent / Me₃P / toluene / -78 - 10 °C

2: TFA / CH₂Cl₂; H₂O / 20 °C

3: EDC; HOBt; Et₃N / dimethylformamide / 20 °C

4: LiOH*H₂O / tetrahydrofuran; H₂O / 24 h / 20 °C

5: H₂; AcOH / Pd(OH)2/C / H₂O / 24 h / 20 °C / atmospheric pressure

With lithium hydroxide; hydrogen; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; trifluoroacetic acid; trimethylphosphane; palladium dihydroxide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1: Staudinger reaction;

DOI:10.1021/jo062588j

upstream raw materials:

phenyl 2,3,5-tri-O-acetyl-1-thio-β-D-ribofuranoside

1,3,2′,6′-tetraazido-6,3′,4′-tri-O-acetylneamine

Downstream raw materials:

5-O-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1-N-tert-butoxycarbonyl-6,3',4'-tri-O-acetyl-3,2',6'-triazidoneamine

5-O-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1-N-[(S)-4-(benzyloxycarbonylamino)-2-hydroxybutanoyl]-6,3',4'-tri-O-acetyl-3,2',6'-triazidoneamine