bao gong teng A

Base Information

• Chemical Name: bao gong teng A
• CAS No.: 74239-84-2
• Molecular Formula: C₉H₁₅NO₃
• Molecular Weight: 185.223
• Mol file: 74239-84-2.mol

Synonyms:8-Azabicyclo[3.2.1]octane-2,6-diol,6-acetate, [1R-(exo,exo)]-; (-)-6b-(Acetyloxy)-2b-hydroxynortropane; (-)-Bao Gong Teng A; (-)-Baogongten A;(1R,2S,5R,6S)-6-(Acetyloxy)-8-azabicyclo[3.2.1]octan-2-ol; (2S,6S)-(-)-2b-Hydroxy-6b-acetoxynortropane; (2S,6S)-2b,6b-Dihydroxynortropane 6-acetate; Alkaloid II fromErycibe obtusifolia; Bao Gong Teng A; Bao Gong Teng C 6-acetate; Base II fromErycibe obtusifolia

Chemical Property of bao gong teng A

Chemical Property:

• Vapor Pressure: 9.75E-05mmHg at 25°C
• Boiling Point: 302.2°C at 760 mmHg
• Flash Point: 136.6°C
• PSA: 58.56000
• Density: 1.22g/cm³
• LogP: 0.13210

Purity/Quality:

98% ^*data from raw suppliers

BaogongtengA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Obtuseleaf Erycibe Stem (Ding Gong Teng) is one of the Chinese herbal medicines recorded by the Pharmacopoeia of the People’s Republic of China (2015). It is a dried rattan from the plants of Convolvulaceae Erycibe obtusifolia Benth. or Erycibe schmidtii Craib. and can be harvested all year. The indications of Ding Gong Teng included rheumatoid arthritis, hemiplegia, swelling, and pain. So Ding Gong Teng is used as a folk medicine to relieve the symptoms of rheumatism in Guangdong and Guangxi provinces. Erycibe alkaloid II belongs to scopolamine alkaloids, whose chemical structure is different from other known cholinomimetic drugs. It has remarkable effects in the treatment of glaucoma by contracting the pupils, reducing the intraocular pressure, and improving the aqueous humor coefficient. It has rare adverse reactions and mild side effects. So erycibe alkaloid II is an ideal drug for the treatment of glaucoma. The content of erycibe alkaloid II is only about one-hundred-thousandth of the original plant. Therefore, efficient synthesis of erycibe alkaloid II is very important for the further research.
• Physical properties: Appearance: white sticky substance. Its benzoate is a white fine acicular crystal. = - °( = ) D C , CHCl 20 3 5.56 0.90 . Melting point: 159–160 °C .
• Clinical Use: The miotic effect, intraocular pressure reduction, and improvement of the coefficient of aqueous outflow are similar between erycibe alkaloid II eye drop and pilocarpine. Furthermore, it has strong myotic effect than pilocarpine without obvious side effects. So it is suitable for long-term application.Erycibe alkaloid II has been shown a good dose-dependent response in both the miosis and the intraocular pressure reduction. The intraocular pressure reduction effects of 0.01% and 0.05% erycibe alkaloid II are similar to that of 1% pilocarpine, and 0.25% erycibe alkaloid II has stronger activity than 1% pilocarpine. The miotic effects of 0.01%, 0.05%, and 0.25% erycibe alkaloid II are similar to that of 1% pilocarpine. There is no significant difference in the intraocular pressure reduction response between 0.05% erycibe alkaloid α and l% pilocarpine after chronic administration (1 month). Both erycibe alkaloid II and pilocarpine are able to improve significantly the coefficient of aqueous outflow without the obvious side effects .Overdose of oral administration or injection of erycibe alkaloid II will cause poisoning, mainly shown as sweating, salivation, asthma, abdominal pain, diarrhea, limb numbness, miosis, blood pressure reduction, bradycardia, etc. It should be paid attention. Local application of erycibe alkaloid II may cause different degrees of blurred vision, conjunctival congestion, and foreign body sensation .

Technology Process of bao gong teng A

There total 13 articles about bao gong teng A 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: 90.0%

(+/-)-(1R,2S,5R,6S)-6-acetyloxy-8-benzyloxycarbonyl-8-azabicyclo[3.2.1]octan-2-ol → Bao Gong Teng A (74239-84-2,107596-26-9,126640-93-5)

Guidance literature:

With hydrogen; palladium dihydroxide; In ethanol; ethyl acetate;

DOI:10.1021/ja055623x

Reference yield: 74.0%

8-benzyl-6-exo-(acetyloxy)-8-azabicyclo<3.2.1>octan-2-exo-ol (141557-09-7) → Bao Gong Teng A (74239-84-2,107596-26-9,126640-93-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 60 ℃; for 4h; under 2280 Torr;

DOI:10.1021/jo00039a005

Reference yield:

(+/-)-(1R,2S,5R,6S)-6-acetyl-8-benzyloxycarbonyl-8-azabicyclo[3.2.1]octan-2-ol → Bao Gong Teng A (74239-84-2,107596-26-9,126640-93-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / m-chloroperbenzoic acid / benzene / 96 h / 20 °C

2: 90 percent / H₂ / Pd(OH)2/C / ethanol; ethyl acetate

With hydrogen; 3-chloro-benzenecarboperoxoic acid; palladium dihydroxide; In ethanol; ethyl acetate; benzene;

DOI:10.1021/ja055623x

upstream raw materials:

8-benzyl-6-exo-(acetyloxy)-8-azabicyclo<3.2.1>octan-2-exo-ol

3-HYDROXYPYRIDINE

1-benzyl-3-hydroxypyridin-1-ium bromide

1-<8-benzyl-2-exo-hydroxy-8-azabicyclo<3.2.1>oct-6-exo-yl>ethanone

Refernces

• 1、 Jung,Longmei,Tangsheng,Huiyan,Yan,Jingyu. "Total synthesis of Bao Gong Teng A, a natural antiglaucoma compound". . p. 3528 - 3530. Retrieved 2007/10/02.