5-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-1,3,2',6'-tetraazido-6,3',4'-tri-O-benzyl neamine

Base Information

• Chemical Name: 5-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-1,3,2',6'-tetraazido-6,3',4'-tri-O-benzyl neamine
• CAS No.: 485810-24-0
• Molecular Formula: C₄₄H₅₀N₁₂O₁₃
• Molecular Weight: 954.954
• Mol file: 485810-24-0.mol

Synonyms:5-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-1,3,2',6'-tetraazido-6,3',4'-tri-O-benzyl neamine

Chemical Property of 5-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-1,3,2',6'-tetraazido-6,3',4'-tri-O-benzyl neamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-1,3,2',6'-tetraazido-6,3',4'-tri-O-benzyl neamine

There total 2 articles about 5-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-1,3,2',6'-tetraazido-6,3',4'-tri-O-benzyl neamine 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:

(1R,2R,5R,6S)-3,5-Diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexanol + 2,3,4-tri-O-acetyl-α-D-xylopyranosyl trichloroacetimidate (128376-91-0,869848-87-3) → Acetic acid (2R,3R,4S,5R)-4,5-diacetoxy-2-[(1R,2R,3S,5R,6S)-3,5-diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexyloxy]-tetrahydro-pyran-3-yl ester + 5-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-1,3,2',6'-tetraazido-6,3',4'-tri-O-benzyl neamine (485810-24-0)

Guidance literature:

(1R,2R,5R,6S)-3,5-Diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexanol; 2,3,4-tri-O-acetyl-α-D-xylopyranosyl trichloroacetimidate; With 4 A molecular sieve; In dichloromethane; at 20 ℃; for 1h;

With boron trifluoride diethyl etherate; In dichloromethane; at -50 ℃; Further stages. Title compound not separated from byproducts.;

DOI:10.1021/ol0269042

Reference yield:

α-D-xylopyranose tetraacetate (1233-03-0,2595-11-1,4026-34-0,4049-33-6,4049-34-7,4257-95-8,4257-98-1,4258-00-8,4627-30-9,17080-99-8,19186-37-9,25227-11-6,25243-38-3,62446-93-9,62929-49-1,67226-03-3,78087-60-2,78088-17-2,82890-16-2,86782-34-5,86782-35-6,92218-63-8,99880-95-2,108646-05-5,115939-79-2,123163-97-3,142130-89-0) → 5-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-1,3,2',6'-tetraazido-6,3',4'-tri-O-benzyl neamine (485810-24-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydrazine acetate / dimethylformamide / 20 °C

1.2: 80 percent / DBU / CH₂Cl₂ / 20 °C

2.1: 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 20 °C

2.2: BF₃*OEt₂ / CH₂Cl₂ / -50 °C

With 4 A molecular sieve; hydrazinium monoacetate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol0269042

upstream raw materials:

2,3,4-tri-O-acetyl-α-D-xylopyranosyl trichloroacetimidate

α-D-xylopyranose tetraacetate