(+/-)-drupacine

Base Information

• Chemical Name: (+/-)-drupacine
• CAS No.: 24268-97-1
• Molecular Formula: C₁₈H₂₁NO₅
• Molecular Weight: 331.368
• Mol file: 24268-97-1.mol

Synonyms:

Chemical Property of (+/-)-drupacine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-drupacine

There total 11 articles about (+/-)-drupacine 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: 83.0%

(+/-)-11-hydroxycephalotaxine (24268-95-9,49686-55-7,125654-59-3) → (+/-)-drupacine (24268-97-1,49686-57-9,125712-90-5)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; for 5h; Ambient temperature;

Reference yield:

(3aα,4aS*,15bβ,15cα)-(+/-)-3a,10,15b,15c-tetrahydro-2,2-dimethyl-7H-<1,3>dioxolo<4,5-h>-1,3-dioxolo<4,5>cyclopenta<1,2-a>-<3>pyrrolo<2,1-b><3>benzazapin-9(4H)-one (113668-87-4,113724-90-6) → (+/-)-drupacine (24268-97-1,49686-57-9,125712-90-5)

Guidance literature:

Multi-step reaction with 9 steps

1: LDA / 1.) THF, o deg C, 0.5 h, 2.) a) THF, HMPA, -78 deg C, 0.5 h, b) 0 deg C, 0.5 h

2: 1.) LHMDS / 1.) a) toluene, 0 deg C, 1 h, b) RT, 0.5 h, 2.) toluene, HMPA, 1 h

3: 81 percent / BH₃*THF / tetrahydrofuran / 1.) -78 deg C, 12 h, 2.) -78 deg C to RT, 15 h

4: 96 percent / pyridine, DMAP / CH₂Cl₂ / 3 h / Ambient temperature

5: 90 percent / 1 N aq. HCl / tetrahydrofuran / 6.5 h / Ambient temperature

6: 89 percent / 1.) DMSO, trifluoroacetic anhydride, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1.5 h, 2.) 0 deg C, 0.5 h

7: 43 percent / p-toluenesulfonic acid monohydrate / diethyl ether / 6 h / Heating

8: 88 percent / NaBH₄ / methanol; CH₂Cl₂ / 3 h / Ambient temperature

9: 83 percent / 1N HCl / tetrahydrofuran / 5 h / Ambient temperature

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; borane-THF; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; lithium hexamethyldisilazane; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

Reference yield:

C20H23NO6 (130552-95-3,130694-07-4) → (+/-)-drupacine (24268-97-1,49686-57-9,125712-90-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) Et₃N, methanesulfonyl chloride, 2.) NaH / 1.) CH₂Cl₂, 0 deg C, 1.5 h, 2.) THF, 15 h

2: LDA / 1.) THF, o deg C, 0.5 h, 2.) a) THF, HMPA, -78 deg C, 0.5 h, b) 0 deg C, 0.5 h

3: 1.) LHMDS / 1.) a) toluene, 0 deg C, 1 h, b) RT, 0.5 h, 2.) toluene, HMPA, 1 h

4: 81 percent / BH₃*THF / tetrahydrofuran / 1.) -78 deg C, 12 h, 2.) -78 deg C to RT, 15 h

5: 96 percent / pyridine, DMAP / CH₂Cl₂ / 3 h / Ambient temperature

6: 90 percent / 1 N aq. HCl / tetrahydrofuran / 6.5 h / Ambient temperature

7: 89 percent / 1.) DMSO, trifluoroacetic anhydride, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1.5 h, 2.) 0 deg C, 0.5 h

8: 43 percent / p-toluenesulfonic acid monohydrate / diethyl ether / 6 h / Heating

9: 88 percent / NaBH₄ / methanol; CH₂Cl₂ / 3 h / Ambient temperature

10: 83 percent / 1N HCl / tetrahydrofuran / 5 h / Ambient temperature

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; borane-THF; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; trifluoroacetic anhydride; lithium hexamethyldisilazane; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

upstream raw materials:

(+/-)-11-hydroxycephalotaxine

(3aα,4aS*,15bβ,15cα)-(+/-)-10-oxo-3a,6,7,15b,15c-pentahydro-2,2-dimethyl-5H-<1,3>dioxolo<4,5-h>-1,3-dioxolo<4,5>cyclopenta<1,2-a>pyrrolo-<2,1-b><3>benzazepin-9(4H)-one

(1aα,2α,3aS*,9β,14bα)-(+/-)-9-acetoxy-1,2,3,5,6,8,9,14b-octahydro-4H-cyclopenta<1,3>dioxolo<4,5-h>pyrrolo<2,1-b><3>benzazepine-1,2-diol

(3aS*,9β)-(+/-)-9-acetoxy-5,6,8,9-tetrahydro-1-hydroxy-4H-cyclopenta<1,3>dioxolo<4,5-h>pyrrolo<2,1-b><3>benzazepin-2-(3H)-one