Jawsamycin

Base Information

• Chemical Name: Jawsamycin
• CAS No.: 120500-69-8
• Molecular Formula: C₃₂H₄₃N₃O₆
• Molecular Weight: 565.71
• DSSTox Substance ID: DTXSID401098276
• Nikkaji Number: J1.420.787B
• Wikidata: Q106038517
• Metabolomics Workbench ID: 200635
• Mol file: 120500-69-8.mol

Synonyms:FR 900848;FR-900848

Chemical Property of Jawsamycin

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 128.20000
• Density: 1.466g/cm³
• LogP: 3.01780
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 565.31518610
• Heavy Atom Count: 41
• Complexity: 1170

Purity/Quality:

97% ^*data from raw suppliers

FR 900848 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC1C=CC2CC2C3CC3C4CC4C5CC5C=CC=CC(=O)NCC6C(C(C(O6)N7CCC(=O)NC7=O)O)O
• Isomeric SMILES: C[C@@H]1C[C@H]1/C=C/[C@@H]2C[C@H]2[C@@H]3C[C@H]3[C@@H]4C[C@H]4[C@@H]5C[C@H]5/C=C/C=C/C(=O)NC[C@@H]6[C@H]([C@H]([C@@H](O6)N7CCC(=O)NC7=O)O)O

Technology Process of Jawsamycin

There total 26 articles about Jawsamycin 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: 76.0%

5’-amino-5’-deoxy-5,6-dihydrouridine (183617-36-9) + (2E,4E)-5-{(1R,2S,1'R,2'R,1''R,2''R,1'''R,2'''S)-2'''-[(E)-2-((1R,2R)-2-Methyl-cyclopropyl)-vinyl]-[1,2';1',1'';2'',1''']quatercyclopropan-2-yl}-penta-2,4-dienoic acid 4-nitro-phenyl ester (197013-61-9) → FR-900848 (120500-69-8)

Guidance literature:

In N,N-dimethyl-formamide; at 23 ℃; for 3h;

DOI:10.1021/ja961093g

Reference yield: 69.0%

5’-amino-5’-deoxy-5,6-dihydrouridine (183617-36-9) + (1R,3S,4R,6S,7S,9R,10S,12R)-1-<5-hydroxy-5-oxo-1,3(E,E)-pentadien-1-yl>-12-<2-<(1R,2R)-2-methylcyclopropyl>-1(E)-ethen-1-yl>quatercyclopropane (176168-16-4) → FR-900848 (120500-69-8)

Guidance literature:

With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; In N,N-dimethyl acetamide;

DOI:10.1039/cc9960000325

Reference yield:

2',3'-O-isopropylideneuridine (362-43-6) → FR-900848 (120500-69-8)

Guidance literature:

Multi-step reaction with 4 steps

1: HN₃, ADDP, Me₃P

2: H⁺

3: H₂ / Rh/C

4: 76 percent / dimethylformamide / 3 h / 23 °C

With tris-(2-chloro-ethyl)-amine; hydrogen; hydrogen cation; 1,1'-azodicarbonyl-dipiperidine; trimethylphosphane; Rh on carbon; In N,N-dimethyl-formamide;

DOI:10.1021/ja961093g

upstream raw materials:

5’-amino-5’-deoxy-5,6-dihydrouridine

(1R,3S,4R,6S,7S,9R,10S,12R)-1-<5-hydroxy-5-oxo-1,3(E,E)-pentadien-1-yl>-12-<2-<(1R,2R)-2-methylcyclopropyl>-1(E)-ethen-1-yl>quatercyclopropane

(2E,4E)-5-{(1R,2S,1'R,2'R,1''R,2''R,1'''R,2'''S)-2'''-[(E)-2-((1R,2R)-2-Methyl-cyclopropyl)-vinyl]-[1,2';1',1'';2'',1''']quatercyclopropan-2-yl}-penta-2,4-dienoic acid 4-nitro-phenyl ester

(1R,3S,4S,6R)-1,6-bis-<3-hydroxy-1(E)-propen-1-yl>bicyclopropane