ginkgolide B

Base Information

• Chemical Name: ginkgolide B
• CAS No.: 119322-54-2
• Molecular Formula: C₂₀H₂₄O₁₀
• Molecular Weight: 424.405
• Mol file: 119322-54-2.mol

Synonyms:ginkgolide B

Chemical Property of ginkgolide B

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ginkgolide B

There total 23 articles about ginkgolide B 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: 89.0%

C26H38O10Si (112574-09-1) → (+/-)-ginkgolide (15291-77-7,112652-59-2,119322-54-2)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 23 ℃; for 14h;

DOI:10.1021/ja00210a083

Reference yield:

2-(2,2-dimethoxyethyl)-2-cyclopenten-1-one (112532-64-6) → (+/-)-ginkgolide (15291-77-7,112652-59-2,119322-54-2)

Guidance literature:

Multi-step reaction with 21 steps

1: 2.) triethylamine / 1.) ether, -78 deg C, 10 min then -45 deg C, 30 min 2.) ether, -45 deg C, 45 min then -10 deg C, 5 min

2: 65 percent / 1,3,6-trioxane, titanium tetrachloride / CH₂Cl₂ / 1.) -78 deg C, 140 min 2.) -45 deg C, 1 h

3: 1.) LDA / 1.) dimethoxyethane, -78 deg C, 1 h then 0 deg C, 20 min 2.) dimethoxyethane, 0 deg C, 1.5 h then 23 deg C, 1 h

4: 84 percent / Pd(PPh₃)4, n-propylamine, cuprous iodide / benzene / 4 h / 16 °C

6: oxalyl chloride / benzene / 2 h / 23 °C

7: tri-n-butylamine / toluene / 3 h / Heating

8: 86 percent / triphenylmethyl hydroperoxide, 1 N sodium hydroxide / acetone; H₂O / 130 h / -30 °C

9: 98 percent / titanium tetrachloride / CH₂Cl₂ / 1.) 0 deg C, 10 min 2.) 23 deg C, 40 min

10: pyridinium dichromate, 3-Angstroem molecular sieves, acetic acid / CH₂Cl₂ / 1 h / 0 °C

11: 1.) periodic acid, water 2.) camphorsulfonic acid / 1.) methanol, CH₂Cl₂, 0 deg C, 20 min then 23 deg C, 40 min 2.) methanol, 23 deg C

12: 1.) lithium diethylamide 2.) (E)-2-(phenylsulfonyl)-3-phenyloxaziridine / 1.) 0 deg C, 15 min 2.) 0 deg C, 30 min

13: camphorsulfonic acid / CH₂Cl₂ / 24 h / 23 °C

14: 1.) N-bromosuccinimide 2.) 10 M silver nitrate / 1.) CCl₄, irradiation, 10 deg C, 2-3 h 2.) acetonitrile, 23 deg C, 15 min

15: 80 percent / pyridinium tosylate, pyridine / chlorobenzene / 16 h / 135 °C

16: 72 percent / triphenylmethyl hydroperoxide, benzyltrimethylammonium isopropoxide / tetrahydrofuran / 3 h / -10 °C

17: 60 percent / LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 to -30 deg C, 2 h 2.) -30 deg C, 10 h

18: 82 percent / camphorsulfonic acid / CH₂Cl₂ / 15 h / 23 °C

19: 89 percent / 2,6-lutidine / acetonitrile / 1 h / 23 °C

20: 1.) osmium tetroxide 2.) iodine, CaCO₃ / 1.) pyridine 2.) methanol, 23 deg C, 12 h

21: 89 percent / BF₃*Et₂O / CH₂Cl₂ / 14 h / 23 °C

With pyridine; 2,6-dimethylpyridine; propylamine; sodium hydroxide; N-Bromosuccinimide; copper(l) iodide; osmium(VIII) oxide; dipyridinium dichromate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,2,4-trioxane; oxalyl dichloride; tributyl-amine; trityl hydroperoxide; benzyltrimethylammonium isopropoxide; 3 A molecular sieve; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; lithium diethylamide; water; iodine; pyridinium p-toluenesulfonate; titanium tetrachloride; silver nitrate; acetic acid; periodic acid; N-(benzenesulfonyl)-3-phenyloxaziridine; triethylamine; calcium carbonate; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; chlorobenzene; acetone; toluene; acetonitrile; benzene;

DOI:10.1021/ja00210a083

Reference yield:

C18H24O5 (112532-79-3) → (+/-)-ginkgolide (15291-77-7,112652-59-2,119322-54-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) N-bromosuccinimide 2.) 10 M silver nitrate / 1.) CCl₄, irradiation, 10 deg C, 2-3 h 2.) acetonitrile, 23 deg C, 15 min

2: 80 percent / pyridinium tosylate, pyridine / chlorobenzene / 16 h / 135 °C

3: 72 percent / triphenylmethyl hydroperoxide, benzyltrimethylammonium isopropoxide / tetrahydrofuran / 3 h / -10 °C

4: 60 percent / LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 to -30 deg C, 2 h 2.) -30 deg C, 10 h

5: 82 percent / camphorsulfonic acid / CH₂Cl₂ / 15 h / 23 °C

6: 89 percent / 2,6-lutidine / acetonitrile / 1 h / 23 °C

7: 1.) osmium tetroxide 2.) iodine, CaCO₃ / 1.) pyridine 2.) methanol, 23 deg C, 12 h

8: 89 percent / BF₃*Et₂O / CH₂Cl₂ / 14 h / 23 °C

With pyridine; 2,6-dimethylpyridine; N-Bromosuccinimide; osmium(VIII) oxide; trityl hydroperoxide; benzyltrimethylammonium isopropoxide; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; iodine; pyridinium p-toluenesulfonate; silver nitrate; calcium carbonate; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; chlorobenzene; acetonitrile;

DOI:10.1021/ja00210a083

upstream raw materials:

C₂₆H₃₈O₁₀Si

2-(2,2-dimethoxyethyl)-2-cyclopenten-1-one

C₁₈H₂₄O₅

C₂₀H₂₄O₈

Downstream raw materials:

ginkgolide A

C₃₀H₃₄O₁₁S₂