5-O-(tert-butyldimethylsilyl)-13-O-[3-(4-azido-2-hydroxy-5-iodobenzoylamino)propionyl]avermectin B_1a aglycone

Base Information

• Chemical Name: 5-O-(tert-butyldimethylsilyl)-13-O-[3-(4-azido-2-hydroxy-5-iodobenzoylamino)propionyl]avermectin B_1a aglycone
• CAS No.: 261911-96-0
• Molecular Formula: C₅₀H₆₉IN₄O₁₁Si
• Molecular Weight: 1057.11

Synonyms:5-O-(tert-butyldimethylsilyl)-13-O-[3-(4-azido-2-hydroxy-5-iodobenzoylamino)propionyl]avermectin B_1a aglycone

Chemical Property of 5-O-(tert-butyldimethylsilyl)-13-O-[3-(4-azido-2-hydroxy-5-iodobenzoylamino)propionyl]avermectin B_1a aglycone

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Technology Process of 5-O-(tert-butyldimethylsilyl)-13-O-[3-(4-azido-2-hydroxy-5-iodobenzoylamino)propionyl]avermectin B_1a aglycone

There total 2 articles about 5-O-(tert-butyldimethylsilyl)-13-O-[3-(4-azido-2-hydroxy-5-iodobenzoylamino)propionyl]avermectin B_1a aglycone 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: 66.0%

4-azido-2-hydroxy-5-iodobenzoic acid N-hydroxysuccinimide ester (99298-06-3) + 5-O-(tert-butyldimethylsilyl)-13-O-(3-aminopropionyl)avermectin B1a aglycone (261911-87-9) → 5-O-(tert-butyldimethylsilyl)-13-O-[3-(4-azido-2-hydroxy-5-iodobenzoylamino)propionyl]avermectin B1a aglycone (261911-96-0)

Guidance literature:

In dichloromethane; at 0 - 20 ℃; for 25.5h;

DOI:10.1016/S0968-0896(99)00259-X

Reference yield:

5-O-(tert-butyldimethylsilyl)-13-O-[3-(2,2,2-trichloroethoxycarbonylamino)propionyl]avermectin B1a aglycone (261911-86-8) → 5-O-(tert-butyldimethylsilyl)-13-O-[3-(4-azido-2-hydroxy-5-iodobenzoylamino)propionyl]avermectin B1a aglycone (261911-96-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 57 percent / zinc; acetic acid; water / tetrahydrofuran / 4.5 h / 20 °C

2: 66 percent / CH₂Cl₂ / 25.5 h / 0 - 20 °C

With water; acetic acid; zinc; In tetrahydrofuran; dichloromethane; 1: Reduction / 2: Acylation;

DOI:10.1016/S0968-0896(99)00259-X

Reference yield: 91.0%

5-O-(tert-butyldimethylsilyl)-13-O-[3-(4-azido-2-hydroxy-5-iodobenzoylamino)propionyl]avermectin B1a aglycone (261911-96-0) → C44H55IN4O11

Guidance literature:

With pyridine hydrogenfluoride; In acetonitrile; at 20 ℃; for 4h;

DOI:10.1016/S0968-0896(99)00259-X

upstream raw materials:

4-azido-2-hydroxy-5-iodobenzoic acid N-hydroxysuccinimide ester

5-O-(tert-butyldimethylsilyl)-13-O-(3-aminopropionyl)avermectin B_1a aglycone

5-O-(tert-butyldimethylsilyl)-13-O-[3-(2,2,2-trichloroethoxycarbonylamino)propionyl]avermectin B_1a aglycone

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