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

Base Information

• Chemical Name: 2-deoxy-6-O-(3-deoxy-3-tosylamido-α-D-glucopyranosyl)-1,3-di-N-tosylstreptamine
• CAS No.: 103358-05-0
• Molecular Formula: C₃₃H₄₃N₃O₁₃S₃
• Molecular Weight: 785.915
• Mol file: 103358-05-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 6 articles about 2-deoxy-6-O-(3-deoxy-3-tosylamido-α-D-glucopyranosyl)-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: 44.0%

1,3,6',3''-tetra-N-tosylkanamycin A (179533-31-4) → 2-deoxy-6-O-(3-deoxy-3-tosylamido-α-D-glucopyranosyl)-1,3-di-N-tosylstreptamine (103358-05-0)

Guidance literature:

1,3,6',3''-tetra-N-tosylkanamycin A; With lead(IV) acetate; In pyridine; at 20 ℃; for 3h;

With sodium tetrahydroborate; In methanol; for 3.5h;

DOI:10.1016/0008-6215(96)00051-1

Reference yield:

3',4'-anhydro-6'-N-(benzyloxycarbonyl)-4'-epi-1,3,3''-tri-N-tosylkanamycin A (144218-67-7) → 6'-N-(benzyloxycarbonyl)-4'-deoxy-4'-fluoro-1,3,3''-tri-N-tosylkanamycin A (144218-68-8) + 6'-N-(benzyloxycarbonyl)-3'-deoxy-3',4'-diepi-3'-fluoro-1,3,3''-tri-N-tosylkanamycin A (144218-69-9) + 6'-N-(benzyloxycarbonyl)-4'-O-(2-hydroxyethyl)-1,3,3''-tri-N-tosylkanamycin A (144218-70-2) + 2-deoxy-6-O-(3-deoxy-3-tosylamido-α-D-glucopyranosyl)-1,3-di-N-tosylstreptamine (103358-05-0)

Guidance literature:

With potassium hydrogen bifluoride; In ethylene glycol; at 150 ℃; for 6h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1016/S0008-6215(00)90996-0

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → 2-deoxy-6-O-(3-deoxy-3-tosylamido-α-D-glucopyranosyl)-1,3-di-N-tosylstreptamine (103358-05-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 64 percent / Na₂CO₃ / dioxane; H₂O / 8.5 h

2.1: Pb(OAc)4 / pyridine / 3 h / 20 °C

2.2: 44 percent / NaBH₄ / methanol / 3.5 h

With lead(IV) acetate; sodium carbonate; In 1,4-dioxane; pyridine; water; 1.1: Tosylation / 2.1: Oxidation / 2.2: Reduction;

DOI:10.1016/0008-6215(96)00051-1

upstream raw materials:

ethylene glycol

3',4'-anhydro-6'-N-(benzyloxycarbonyl)-4'-epi-1,3,3''-tri-N-tosylkanamycin A

1,3,6',3''-tetra-N-tosylkanamycin A

p-toluenesulfonyl chloride

Downstream raw materials:

2-Deoxy-6-O-(3-deoxy-4,6-O-isopropylidene-3-tosylamido-α-D-glucopyranosyl)-4,5-O-isopropylidene-1,3-di-N-tosylstreptamine

6-O-(2-O-Benzylsulfonyl-3-deoxy-4,6-O-isopropylidene-3-tosylamido-α-D-glucopyranosyl)-2-deoxy-4,5-O-isopropylidene-1,3-di-N-tosylstreptamine

2-Deoxy-6-O-(2,3-dideoxy-4,6-O-isopropylidene-2,3-N-tosylepimino-α-D-mannopyranosyl)-4,5-O-isopropylidene-1,3-di-N-tosylstreptamine

2-Deoxy-6-O-(2,3-dideoxy-2,3-N-tosylepimino-α-D-mannopyranosyl)-1,3-di-N-tosylstreptamine