Sesbanimide

Base Information

• Chemical Name: Sesbanimide
• CAS No.: 85719-78-4
• Molecular Formula: C₁₅H₂₁NO₇
• Molecular Weight: 327.334
• Mol file: 85719-78-4.mol

Synonyms:

Chemical Property of Sesbanimide

Chemical Property:

• Vapor Pressure: 7.31E-17mmHg at 25°C
• Boiling Point: 599.3°C at 760 mmHg
• Flash Point: 316.3°C
• PSA: 117.81000
• Density: 1.4g/cm³
• LogP: -0.67140

Purity/Quality:

Sesbanimide A ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Sesbanimide A is an antiproliferative antitumor alkaloid initially extracted from the seeds of seeds of the leguminous plants Sesbania drummondii and Sesbania punicea.

Technology Process of Sesbanimide

There total 138 articles about Sesbanimide 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: 100.0%

4-[(4R,5S,6R)-6-[(S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-2-methyl-but-3-enoyl]-5-(tert-butyl-diphenyl-silanyloxy)-[1,3]dioxan-4-yl]-piperidine-2,6-dione (102615-87-2) → (-)-sesbanimide A (85719-78-4,92282-10-5,94199-33-4,95839-03-5,102680-31-9,141554-45-2,141554-46-3,141554-47-4)

Guidance literature:

With acetic acid; In tetrahydrofuran; water; at 22 ℃; for 4.3h;

DOI:10.1021/jo00363a051

Reference yield: 86.0%

4-{(4R,5S,6R)-6-[(S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-2-methyl-but-3-enoyl]-5-hydroxy-[1,3]dioxan-4-yl}-piperidine-2,6-dione (113425-71-1) → (-)-sesbanimide A (85719-78-4,92282-10-5,94199-33-4,95839-03-5,102680-31-9,141554-45-2,141554-46-3,141554-47-4)

Guidance literature:

With acetic acid; In tetrahydrofuran; water;

DOI:10.1016/S0040-4020(01)81662-8

Reference yield: 82.0%

(1R,2S,6R,9S)-(-)-9-(tert-butyldiphenylsilyloxy)-6-<(2R)-1-oxo-2-methyl-3-methylene-4-(tert-butyldimethylsilyloxy)butyl>-3,5,8-trioxa-10-azatricyclo<7.3.1.02,7>tridecan-11-one (138832-14-1) → (+)-sesbanimide A (85719-78-4,92282-10-5,94199-33-4,95839-03-5,102680-31-9,141554-45-2,141554-46-3,141554-47-4)

Guidance literature:

With water; acetic acid; In tetrahydrofuran; for 3h; Ambient temperature;

upstream raw materials:

(1R,2S,6R,9S)-(-)-9-(tert-butyldiphenylsilyloxy)-6-<(2R)-1-oxo-2-methyl-3-methylene-4-(tert-butyldimethylsilyloxy)butyl>-3,5,8-trioxa-10-azatricyclo<7.3.1.0^2,7>tridecan-11-one

(4'S,5'R,6'R)-4-6'-1,4-dihydroxy-2-methyl-3-methylene-butyryl-5'-tert-butyldimethylsiloxy-1'-3'-dioxan-4'-yl-2,6-piperidinedione

4-{(4S,5R,6S)-6-[(R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-2-methyl-but-3-enoyl]-5-hydroxy-[1,3]dioxan-4-yl}-piperidine-2,6-dione

ethyl (E)-2-(bromomethyl)but-2-enoate

Refernces

EFFICIENT SYNTHESIS AND ANTITUMOR ACTIVITY OF AN ENANTIOMERIC PAIR OF THE SESBANIMIDE AB-RING SYSTEMS

10.1016/S0040-4039(00)98773-2

This study focused on the synthesis and antitumor activity of the AB ring system enantiomers of Sesbanimide A, a potent antitumor alkaloid isolated from the seeds of Sesbania drummondii and S. punices. The researchers efficiently synthesized the fully unprotected AB ring system enantiomers from readily available D- and L-xylose. The synthetic route involved several steps, including hydroxyl protection, ring opening and carbon chain extension, construction of the dioxane ring, Michael addition, demethoxycarbonylation, and catalytic hydrogenation. The synthesized compounds were then tested for in vitro antitumor activity against P388 murine leukemia, and the results showed that the AB ring system itself contributed little to the cytotoxicity of Sesbanimide A, indicating that the significant antitumor activity of Sesbanimide A mainly comes from its characteristic C ring.