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

Base Information

Chemical Name:5-O-(4-azido-2,3,6-tri-O-acetyl-4-deoxy-β-D-glucopyranosyl)-1,3,2',6'-tetraazido-6,3',4'-tri-O-benzyl neamine
CAS No.:485810-13-7
Molecular Formula:C₄₅H₅₁N₁₅O₁₃
Molecular Weight:1009.99
Hs Code.:

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

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

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

There total 2 articles about 5-O-(4-azido-2,3,6-tri-O-acetyl-4-deoxy-β-D-glucopyranosyl)-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: 71.0%

: (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

: 485809-84-5
4-azido-2,3,6-tri-O-acetyl-4-deoxy-α-D-glucopyranosyl trichloroacetimidate

: 485810-13-7
5-O-(4-azido-2,3,6-tri-O-acetyl-4-deoxy-β-D-glucopyranosyl)-1,3,2',6'-tetraazido-6,3',4'-tri-O-benzyl neamine

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; 4-azido-2,3,6-tri-O-acetyl-4-deoxy-α-D-glucopyranosyl trichloroacetimidate; With 4 A molecular sieve; In dichloromethane; at 20 ℃; for 1h;

With boron trifluoride diethyl etherate; In dichloromethane; at -50 ℃; Further stages.;
DOI:10.1021/ol0269042

Reference yield:

: 4098-00-4
acetyl 4-azido-2,3,6-tri-O-acetyl-4-deoxy-α-D-glucopyranoside

: 485810-13-7
5-O-(4-azido-2,3,6-tri-O-acetyl-4-deoxy-β-D-glucopyranosyl)-1,3,2',6'-tetraazido-6,3',4'-tri-O-benzyl neamine

Guidance literature:: Multi-step reaction with 2 steps

1.1: hydrazine acetate / dimethylformamide / 20 °C

1.2: 34 percent / DBU / CH₂Cl₂ / 20 °C

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

2.2: 71 percent / BF₃*OEt₂ / CH₂Cl₂ / -50 °C

With 4 A molecular sieve; hydrazinium monoacetate; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol0269042