142680-85-1

Basic information

• Product Name: (25S)-25-CYCLOHEXYL-25-DE(SEC-BUTYL)-5-O-DEMETHYL-22,23-DIHYDROAVERMECTIN A1A
• Synonyms: (25S)-25-CYCLOHEXYL-25-DE(SEC-BUTYL)-5-O-DEMETHYL-22,23-DIHYDROAVERMECTIN A1A
• CAS NO: 142680-85-1
• Molecular Formula: C50H76O14
• Molecular Weight: 901.14
• Mol File: 142680-85-1.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Density: 1.103[at 20℃]
• Vapor Pressure: 24Pa at 20℃
• Water Solubility: 950μg/L at 20℃
• CAS DataBase Reference: (25S)-25-CYCLOHEXYL-25-DE(SEC-BUTYL)-5-O-DEMETHYL-22,23-DIHYDROAVERMECTIN A1A(CAS DataBase Reference)
• NIST Chemistry Reference: (25S)-25-CYCLOHEXYL-25-DE(SEC-BUTYL)-5-O-DEMETHYL-22,23-DIHYDROAVERMECTIN A1A(142680-85-1)
• EPA Substance Registry System: (25S)-25-CYCLOHEXYL-25-DE(SEC-BUTYL)-5-O-DEMETHYL-22,23-DIHYDROAVERMECTIN A1A(142680-85-1)

Safety Data

• Hazardous Substances Data: 142680-85-1(Hazardous Substances Data)

Usage

Uses

22,23-Dihydro-25-cyclohexylavermectin B1 is an intermediate in synthesizing 4''-O-2,6-Dideoxy-3-O-methyl-α-L-arabino-hexopyranosyl Selamectin (D440100), which s an impurity of Selamectin (S247990), a topical parasiticide. Selamectin (S247990) is also used as a veterinary antihelminithic agent on animals.

Flammability and Explosibility

Nonflammable

Upstream product

• 117704-25-3 doramectin 

Downstream Products

• 165108-07-6 [3H]-Selamectin 
• 165108-07-6 C₄₃H₆₃NO₁₁ 

Relevant articles and documents

Synthesis method for high-purity selamectin

The invention provides a synthesis method for high-purity selamectin. The synthesis method comprises the following steps: with doramectin as a raw material, subjecting the doramectin to hydrogenation,oxidation, oximation and desugaring so as to obtain a crude selamectin product, wherein an oxidation system adopted by oxidation is a manganese dioxide/Dess Martin oxidant or manganese dioxide/2-iodoylbenzoic acid. According to the invention, the use of a traditional single oxidant is broken through; the manganese dioxide/Dess Martin oxidant or the manganese dioxide/2-iodoxybenzoic acid is selected as the oxidation system; the oxidation system is mild and controllable; oxidation reaction is more thorough; reaction byproducts are few; thus, the obtained crude selamectin product is high in purity, and conditions are provided for abandoning a C18 high-pressure preparation process in a subsequent refining process. Generally speaking, the synthesis method provided by the invention is short insynthetic route, not tedious in post-treatment process and low in cost, can obtain the selamectin with a purity of 99% or above, and has high total yield.

Preparation method of selamectin

The invention provides an improved preparation technology of selamectin. The improved preparation technology comprises the following steps of (1) in the presence of a Wilson catalyst, reducing the selamectin DL by hydrogen, so as to obtain an intermediate SL1; (2) desugaring the intermediate SL1 obtained in step (1) by an organic solvent hydrochloric acid solution (by dissolving hydrochloric acid gas into an organic solvent), so as to obtain an intermediate SL2; (3) oxidizing the intermediate SL2 obtained in step (2) by manganese dioxide, so as to obtain an intermediate SL3; (4) oximating the intermediate SL3 obtained in step (3) by hydroxylamine hydrochloride, so as to obtain selamectin SL; (5) recrystallizing the crude product of selamectin SL obtained in step (4) by methylbenzene, acetone and methanol, so as to obtain the purified selamectin SL.