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

Base Information

Chemical Name: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
CAS No.:942420-69-1
Molecular Formula:C₄₁H₅₃N₁₁O₂₀
Molecular Weight:1019.93
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 4 articles about 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 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:

: 942420-67-9
5-O-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6,3',4'-tri-O-acetyl-1,3,2',6'-tetraazidoneamine

: 942420-69-1
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

Guidance literature:: Multi-step reaction with 3 steps

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

2: TFA / CH₂Cl₂; H₂O / 20 °C

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

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; trifluoroacetic acid; trimethylphosphane; In dichloromethane; water; N,N-dimethyl-formamide; toluene; 1: Staudinger reaction;
DOI:10.1021/jo062588j

Reference yield:

: 942420-68-0
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

: 942420-69-1
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

Guidance literature:: Multi-step reaction with 2 steps

1: TFA / CH₂Cl₂; H₂O / 20 °C

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

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; trifluoroacetic acid; In dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo062588j

Reference yield:

: 52544-88-4
phenyl 2,3,5-tri-O-acetyl-1-thio-β-D-ribofuranoside

: 942420-69-1
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

Guidance literature:: Multi-step reaction with 4 steps

1: 37 percent / N-iodosuccinimide; trimethylsilyl triflate; 4 Angstroem molecular sieves / CH₂Cl₂ / -50 - 20 °C

2: 31 percent / Me₃P / toluene / -78 - 10 °C

3: TFA / CH₂Cl₂; H₂O / 20 °C

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

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; trifluoroacetic acid; trimethylphosphane; In dichloromethane; water; N,N-dimethyl-formamide; toluene; 2: Staudinger reaction;
DOI:10.1021/jo062588j