2-epiavermectin B_1a

Base Information

• Chemical Name: 2-epiavermectin B_1a
• CAS No.: 131483-64-2
• Molecular Formula: C₄₈H₇₂O₁₄
• Molecular Weight: 873.091
• Mol file: 131483-64-2.mol

Synonyms:

Chemical Property of 2-epiavermectin B_1a

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-epiavermectin B_1a

There total 28 articles about 2-epiavermectin B_1a 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:

Avermectin B1a (171028-71-0) → 2,19-Bis-epi-avermectin B1 (65195-55-3,106434-14-4,113665-88-6,113665-89-7,131483-64-2,135556-35-3,135556-38-6,135681-09-3,144068-48-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 91 percent / imidazole / dimethylformamide / 40 h / 45 °C

2: 56 percent / DBU / 22 h / 57 °C

3: 1) oxalyl chloride, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 45 min., 2) 25 deg C, 45 min.

4: lithium tri-sec-butylborohydride (L-selectride) / tetrahydrofuran / 0.75 h / -78 °C

5: 71 percent / KOH / methanol; H₂O / 65 h / 25 °C

6: Mukaiyama conditions

7: 57 percent / dimethylformamide / 24 h / 25 °C

8: 1) LDA, 2) pivalic acid / tetrahydrofuran / 0.25 h / -78 °C

9: HF, pyridine / tetrahydrofuran

With pyridine; 1H-imidazole; potassium hydroxide; oxalyl dichloride; hydrogen fluoride; L-Selectride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide; Trimethylacetic acid; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(91)85068-G

Reference yield:

avermectin B1a bis(silyl ether) (81924-42-7,106621-62-9,135556-37-5,143956-74-5,144068-49-5) → 2,19-Bis-epi-avermectin B1 (65195-55-3,106434-14-4,113665-88-6,113665-89-7,131483-64-2,135556-35-3,135556-38-6,135681-09-3,144068-48-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 56 percent / DBU / 22 h / 57 °C

2: 1) oxalyl chloride, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 45 min., 2) 25 deg C, 45 min.

3: lithium tri-sec-butylborohydride (L-selectride) / tetrahydrofuran / 0.75 h / -78 °C

4: 71 percent / KOH / methanol; H₂O / 65 h / 25 °C

5: Mukaiyama conditions

6: 57 percent / dimethylformamide / 24 h / 25 °C

7: 1) LDA, 2) pivalic acid / tetrahydrofuran / 0.25 h / -78 °C

8: HF, pyridine / tetrahydrofuran

With pyridine; potassium hydroxide; oxalyl dichloride; hydrogen fluoride; L-Selectride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide; Trimethylacetic acid; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(91)85068-G

Reference yield:

C60H100O14Si2 (103024-46-0,135556-36-4) → 2,19-Bis-epi-avermectin B1 (65195-55-3,106434-14-4,113665-88-6,113665-89-7,131483-64-2,135556-35-3,135556-38-6,135681-09-3,144068-48-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 57 percent / dimethylformamide / 24 h / 25 °C

2: 1) LDA, 2) pivalic acid / tetrahydrofuran / 0.25 h / -78 °C

3: HF, pyridine / tetrahydrofuran

With pyridine; hydrogen fluoride; lithium diisopropyl amide; Trimethylacetic acid; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(91)85068-G

upstream raw materials:

C₆₃H₁₀₈O₁₄Si₃

C₆₀H₁₀₀O₁₄Si₂

C₆₀H₁₀₀O₁₄Si₂

C₆₃H₁₀₈O₁₄Si₃

Downstream raw materials:

(8,9-Z)-avermectin B_1a

(10,11-Z)-avermectin B_1a

avermectin B₁a

Δ²-4(R)-avermectin B_1a