Drupacine

Base Information

• Chemical Name: Drupacine
• CAS No.: 49686-57-9
• Molecular Formula: C18H21NO5
• Molecular Weight: 331.363
• Mol file: 49686-57-9.mol

Synonyms:

Chemical Property of Drupacine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 70-2°C
• Boiling Point: 499.356°C at 760 mmHg
• Flash Point: 255.801°C
• PSA: 60.39000
• Density: 1.49g/cm³
• LogP: 1.46360

Purity/Quality:

98.5% ^*data from raw suppliers

Drupacine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Cephalotaxus harringtonia contains a number of structurally similar alkaloids. This base has newly been isolated from this source and forms colourless crystals from a mixture of MeOH-CHC13-hexane. It is laevorotatory with a specific rotation of [α]26 D- 137° (c 0.79, CHC13) and gives an ultraviolet spectrum in EtOH with absorption maxima at 242 and 291 nm. The crystalline acetate has m.p. 75-90°C.

Technology Process of Drupacine

There total 39 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: 86.0%

11R-hydroxycephalotaxine (49686-55-7) → (-)-drupacine (49686-57-9)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 23 ℃; for 5h;

DOI:10.1021/jo0710883

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;

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

Downstream raw materials:

3-O-Acetyldrupacin

Refernces

• 1、 Liu, Qi,Ferreira, Eric M.,Stoltz, Brian M.. "Convergency and divergency as strategic elements in total synthesis: The total synthesis of (-)-drupacine and the formal total synthesis of (±)-cephalotaxine, (-)-cephalotaxine, and (+)-cephalotaxine". . p. 7352 - 7358. Retrieved 2008/02/12.