6-O-(3-deoxy-3-tosylamido-α-D-glucopyranosyl)-2,5-dideoxy-5-epi-5-fluoro-1,3-di-N-tosylstreptamine

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Chemical Name:6-O-(3-deoxy-3-tosylamido-α-D-glucopyranosyl)-2,5-dideoxy-5-epi-5-fluoro-1,3-di-N-tosylstreptamine
CAS No.:316804-46-3
Molecular Formula:C₃₃H₄₂FN₃O₁₂S₃
Molecular Weight:787.906
Hs Code.:

Synonyms:6-O-(3-deoxy-3-tosylamido-α-D-glucopyranosyl)-2,5-dideoxy-5-epi-5-fluoro-1,3-di-N-tosylstreptamine

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Chemical Property of 6-O-(3-deoxy-3-tosylamido-α-D-glucopyranosyl)-2,5-dideoxy-5-epi-5-fluoro-1,3-di-N-tosylstreptamine

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Technology Process of 6-O-(3-deoxy-3-tosylamido-α-D-glucopyranosyl)-2,5-dideoxy-5-epi-5-fluoro-1,3-di-N-tosylstreptamine

There total 3 articles about 6-O-(3-deoxy-3-tosylamido-α-D-glucopyranosyl)-2,5-dideoxy-5-epi-5-fluoro-1,3-di-N-tosylstreptamine 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: 87.0%

: 316804-45-2
5-deoxy-5-epi-5-fluoro-1,3,6',3''-tetra-N-tosylkanamycin A

: 316804-46-3
6-O-(3-deoxy-3-tosylamido-α-D-glucopyranosyl)-2,5-dideoxy-5-epi-5-fluoro-1,3-di-N-tosylstreptamine

Guidance literature:: 5-deoxy-5-epi-5-fluoro-1,3,6',3''-tetra-N-tosylkanamycin A; With sodium periodate; In methanol; ethylene glycol; at 20 ℃; for 2.5h;

With sodium tetrahydroborate; In methanol; at 20 ℃; for 2.5h;

With hydrogenchloride; In methanol; at 20 ℃; for 5h;
DOI:10.1016/S0008-6215(00)00184-1

Reference yield:

: 2',3',4',2'',4'',6''-hexa-O-acetyl-5-deoxy-5-epi-5-fluoro-1,3,6',3''-tetra-N-tosylkanamycin A

: 316804-46-3
6-O-(3-deoxy-3-tosylamido-α-D-glucopyranosyl)-2,5-dideoxy-5-epi-5-fluoro-1,3-di-N-tosylstreptamine

Guidance literature:: Multi-step reaction with 2 steps

1.1: 99 percent / NaOMe / methanol / 0.5 h / 20 °C

2.1: NaIO₄ / methanol; ethane-1,2-diol / 2.5 h / 20 °C

2.2: NaBH₄ / methanol / 2.5 h / 20 °C

2.3: 87 percent / aq. HCl / methanol / 5 h / 20 °C

With sodium periodate; sodium methylate; In methanol; ethylene glycol; 2.1: Smith degradation;
DOI:10.1016/S0008-6215(00)00184-1

Reference yield:

: 2',3',4',2'',4'',6''-hexa-O-acetyl-1,3,6',3''-tetra-N-tosylkanamycin A

: 316804-46-3
6-O-(3-deoxy-3-tosylamido-α-D-glucopyranosyl)-2,5-dideoxy-5-epi-5-fluoro-1,3-di-N-tosylstreptamine

Guidance literature:: Multi-step reaction with 3 steps

1.1: 100 percent / Et₂NSF₃ / CH₂Cl₂ / 2.5 h / 0 °C

2.1: 99 percent / NaOMe / methanol / 0.5 h / 20 °C

3.1: NaIO₄ / methanol; ethane-1,2-diol / 2.5 h / 20 °C

3.2: NaBH₄ / methanol / 2.5 h / 20 °C

3.3: 87 percent / aq. HCl / methanol / 5 h / 20 °C

With sodium periodate; diethylamino-sulfur trifluoride; sodium methylate; In methanol; dichloromethane; ethylene glycol; 3.1: Smith degradation;
DOI:10.1016/S0008-6215(00)00184-1