5-O-(4-azido-4,6-dideoxy-β-D-glucopyranosyl)-1-N-[(S)-4-(benzyloxycarbonyl-amino)-2-hydroxybutanoyl]-3,2',6'-triazido-3',4'-dideoxy-3'-enoneamine

Base Information

• Chemical Name: 5-O-(4-azido-4,6-dideoxy-β-D-glucopyranosyl)-1-N-[(S)-4-(benzyloxycarbonyl-amino)-2-hydroxybutanoyl]-3,2',6'-triazido-3',4'-dideoxy-3'-enoneamine
• CAS No.: 882050-17-1
• Molecular Formula: C₃₀H₄₀N₁₄O₁₁
• Molecular Weight: 772.735
• Mol file: 882050-17-1.mol

Synonyms:5-O-(4-azido-4,6-dideoxy-β-D-glucopyranosyl)-1-N-[(S)-4-(benzyloxycarbonyl-amino)-2-hydroxybutanoyl]-3,2',6'-triazido-3',4'-dideoxy-3'-enoneamine

Chemical Property of 5-O-(4-azido-4,6-dideoxy-β-D-glucopyranosyl)-1-N-[(S)-4-(benzyloxycarbonyl-amino)-2-hydroxybutanoyl]-3,2',6'-triazido-3',4'-dideoxy-3'-enoneamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-O-(4-azido-4,6-dideoxy-β-D-glucopyranosyl)-1-N-[(S)-4-(benzyloxycarbonyl-amino)-2-hydroxybutanoyl]-3,2',6'-triazido-3',4'-dideoxy-3'-enoneamine

There total 8 articles about 5-O-(4-azido-4,6-dideoxy-β-D-glucopyranosyl)-1-N-[(S)-4-(benzyloxycarbonyl-amino)-2-hydroxybutanoyl]-3,2',6'-triazido-3',4'-dideoxy-3'-enoneamine 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: 91.0%

5-O-(4-azido-4,6-dideoxy-β-D-glucopyranosyl)-1-N-tert-butoxycatbonyl-3,2',6'-triazido-3',4'-dideoxy-3'-enoneamine (882050-16-0) + S-4-benzyloxycarbonylamino-2-hydroxybutyric acid (40371-50-4) → 5-O-(4-azido-4,6-dideoxy-β-D-glucopyranosyl)-1-N-[(S)-4-(benzyloxycarbonyl-amino)-2-hydroxybutanoyl]-3,2',6'-triazido-3',4'-dideoxy-3'-enoneamine (882050-17-1)

Guidance literature:

5-O-(4-azido-4,6-dideoxy-β-D-glucopyranosyl)-1-N-tert-butoxycatbonyl-3,2',6'-triazido-3',4'-dideoxy-3'-enoneamine; With trifluoroacetic acid; In dichloromethane;

S-4-benzyloxycarbonylamino-2-hydroxybutyric acid; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide;

Reference yield:

(2S,3R,4S,5S,6R)-2-[(1R,2S,3R,5S,6R)-3-Amino-5-azido-6-((2R,3R,6S)-3-azido-6-azidomethyl-3,6-dihydro-2H-pyran-2-yloxy)-2-hydroxy-cyclohexyloxy]-5-azido-6-methyl-tetrahydro-pyran-3,4-diol + S-4-benzyloxycarbonylamino-2-hydroxybutyric acid (40371-50-4) → 5-O-(4-azido-4,6-dideoxy-β-D-glucopyranosyl)-1-N-[(S)-4-(benzyloxycarbonyl-amino)-2-hydroxybutanoyl]-3,2',6'-triazido-3',4'-dideoxy-3'-enoneamine (882050-17-1)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/ol0529750

Reference yield:

1,3,2',6'-tetraazido-3',4'-dideoxy-3'-enoneamine (860640-70-6) → 5-O-(4-azido-4,6-dideoxy-β-D-glucopyranosyl)-1-N-[(S)-4-(benzyloxycarbonyl-amino)-2-hydroxybutanoyl]-3,2',6'-triazido-3',4'-dideoxy-3'-enoneamine (882050-17-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 82 percent / DMAP; Et₃N / CH₂Cl₂ / 48 h / 20 °C

2: 84 percent / PMe₃ / toluene / -78 - -10 °C

3: 87 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 0 - 20 °C

4: 99 percent / DIPEA / CH₂Cl₂ / -50 - 0 °C

5: BF₃*Et₂O; molecular sieves 4 Angstroem / CH₂Cl₂

6: 0.66 g / NaOMe / methanol; tetrahydrofuran / 2 h / 20 °C

7: trifluoroacetic acid / CH₂Cl₂ / 3 h / 20 °C

8: 0.86 g / EDC; HOBt; Et₃N / dimethylformamide / 20 °C

With dmap; lithium hydroxide; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium methylate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; trimethylphosphane; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 2: Staudinger reaction;

DOI:10.1021/ol0529750

upstream raw materials:

S-4-benzyloxycarbonylamino-2-hydroxybutyric acid

1,3,2',6'-tetraazido-3',4'-dideoxy-3'-enoneamine

1-N-tet-butoxycarbonyl-3,2',6'-triazido-3',4'-dideoxy-3'-enoneamine

6-O-benzoyl-1-N-tet-butoxycarbonyl-3,2',6'-triazido-3',4'-dideoxy-3'-enoneamine