(+/-)-chuangxinmycin trans-isomer

Base Information

• Chemical Name: (+/-)-chuangxinmycin trans-isomer
• CAS No.: 83602-20-4
• Molecular Formula: C₁₂H₁₁NO₂S
• Molecular Weight: 233.291
• Mol file: 83602-20-4.mol

Synonyms:

Chemical Property of (+/-)-chuangxinmycin trans-isomer

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-chuangxinmycin trans-isomer

There total 13 articles about (+/-)-chuangxinmycin trans-isomer 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: 40.0%

(+/-)-chuangxinmycin methyl ester (83602-19-1) → 2-carboxyl-3-methyl-3,5-dihydro-2H-thiopyrano[4,3,2-cd]indole (478916-44-8,63339-68-4) + (+/-)-chuangxinmycin trans-isomer (83602-20-4,63339-68-4)

Guidance literature:

With sodium hydroxide; In ethanol; water; Ambient temperature;

DOI:10.1021/ja00390a037

Reference yield: 18.0%

3-Methyl-3,5-dihydro-2H-thiopyrano[4,3,2-cd]indole-2-carboxylic acid methyl ester (148407-04-9) → 2-carboxyl-3-methyl-3,5-dihydro-2H-thiopyrano[4,3,2-cd]indole (478916-44-8,63339-68-4) + (+/-)-chuangxinmycin trans-isomer (83602-20-4,63339-68-4)

Guidance literature:

With sodium hydroxide; In ethanol; for 17h; Yields of byproduct given; Ambient temperature;

DOI:10.1248/cpb.42.271

Reference yield:

2,6-dinitrotoluene (606-20-2) → (+/-)-chuangxinmycin trans-isomer (83602-20-4,63339-68-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 51 percent / dimethylformamide / 24 h / 125 °C

2: 93 percent / Nh₄Cl / ethanol / 24 h / Heating

3: 63 percent / LiOH / hexamethylphosphoric acid triamide / 24 h / Ambient temperature

4: 1.) H₂, 2.) 6N HCl / 1.) 5percent Pd/C sulfided catalyst / 1.) EtOAc, 40 psi, 3 h, 2.) CH₂Cl₂, reflux, 2 h

5: 92 percent / SnCl₄ / benzene / 1.) 0 deg C, 20 min, 2.) room temperature, 2 h

6: 94 percent / NH₄OAc*H₂O, AcOH / benzene / 15 h / Heating

7: 40 percent / H₂ / sulfided 5percent Pd/C / ethyl acetate / 72 h / 3620.04 Torr

8: NaOH / H₂O; ethanol / Ambient temperature

With hydrogenchloride; lithium hydroxide; sodium hydroxide; ammonium acetate; hydrogen; tin(IV) chloride; ammonium chloride; acetic acid; Pd/C sulfided catalyst; In N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; water; ethyl acetate; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja00390a037

upstream raw materials:

(+/-)-chuangxinmycin methyl ester

3-Methyl-3,5-dihydro-2H-thiopyrano[4,3,2-cd]indole-2-carboxylic acid methyl ester

2,6-dinitrotoluene

methyl ester of 4-indolylthioacetic acid