Capuramycin

Base Information

• Chemical Name: Capuramycin
• CAS No.: 102770-00-3
• Molecular Formula: C23H31 N5 O12
• Molecular Weight: 569.525
• UNII: 624X0OXY6Y
• DSSTox Substance ID: DTXSID501318180
• Nikkaji Number: J358.667G
• Wikidata: Q76309600
• Metabolomics Workbench ID: 94578
• ChEMBL ID: CHEMBL96695
• Mol file: 102770-00-3.mol

Synonyms:capuramycin

Chemical Property of Capuramycin

Chemical Property:

• Boiling Point: °Cat760mmHg
• PKA: 9.39±0.10(Predicted)
• Flash Point: °C
• PSA: 253.76000
• Density: 1.6g/cm³
• LogP: -3.15270
• XLogP3: -4.1
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 8
• Exact Mass: 569.19692144
• Heavy Atom Count: 40
• Complexity: 1100

Purity/Quality:

98% ^*data from raw suppliers

CAPURAMYCIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(C(OC1C(C(=O)N)OC2C(C(C=C(O2)C(=O)NC3CCCCNC3=O)O)O)N4C=CC(=O)NC4=O)O
• Isomeric SMILES: CO[C@H]1[C@H]([C@@H](O[C@@H]1[C@H](C(=O)N)O[C@@H]2[C@H]([C@H](C=C(O2)C(=O)N[C@H]3CCCCNC3=O)O)O)N4C=CC(=O)NC4=O)O
• Recent ClinicalTrials: Biocell Natural Killer Mixture in Diffuse Large B Cell Lymphoma (DLBCL) Patients

Technology Process of Capuramycin

There total 57 articles about Capuramycin 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%

C29H37N5O15 (1158951-70-2) → 1-[5-O-[4,6-dideoxy-6-oxo-6-[[[(3S)-hexahydro-2-oxo-1H-azepine]-3-yl]amino]-β-L-erythro-4-hexenopyranosyl]-3-O-methyl 6-deoxy-6-amino-α-L-talofuranuronosyl]-1,2,3,4-tetrahydro-2,4-dioxopyrimidine (102770-00-3)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 0 - 20 ℃;

DOI:10.1021/ol900458w

Reference yield: 99.0%

C34H39N5O15 → 1-[5-O-[4,6-dideoxy-6-oxo-6-[[[(3S)-hexahydro-2-oxo-1H-azepine]-3-yl]amino]-β-L-erythro-4-hexenopyranosyl]-3-O-methyl 6-deoxy-6-amino-α-L-talofuranuronosyl]-1,2,3,4-tetrahydro-2,4-dioxopyrimidine (102770-00-3)

Guidance literature:

With sodium hydroxide; In methanol; water; at 0 - 20 ℃;

DOI:10.1039/d0sc06815b

Reference yield: 60.0%

2,2-Dimethyl-propionic acid (2R,3R,4R,5S)-5-{(R)-carbamoyl-[(2S,3S,4S)-3,4-diacetoxy-6-((S)-2-oxo-azepan-3-ylcarbamoyl)-3,4-dihydro-2H-pyran-2-yloxy]-methyl}-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-methoxy-tetrahydro-furan-3-yl ester → 1-[5-O-[4,6-dideoxy-6-oxo-6-[[[(3S)-hexahydro-2-oxo-1H-azepine]-3-yl]amino]-β-L-erythro-4-hexenopyranosyl]-3-O-methyl 6-deoxy-6-amino-α-L-talofuranuronosyl]-1,2,3,4-tetrahydro-2,4-dioxopyrimidine (102770-00-3)

Guidance literature:

With sodium hydroxide; In methanol; for 2.5h;

DOI:10.1021/jo00081a004

upstream raw materials:

1,2,3,4-tetra-O-acetyl-D-mannopyranoside

1-[6-methoxy-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro-[2,3-d][1,3]dioxol-5-yl]-(1R)-ethane-1,2-diol

2,2-Dimethyl-propionic acid (2R,3R,4R,5R)-5-((S)-1-acetoxy-2-benzyloxy-ethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-methoxy-tetrahydro-furan-3-yl ester

Acetic acid (S)-2-benzyloxy-1-((2R,3S,4R,5S)-4,5-dihydroxy-3-methoxy-tetrahydro-furan-2-yl)-ethyl ester

Downstream raw materials:

C₄₃H₆₅N₅O₁₃SSi₂

C₄₂H₆₃N₅O₁₃SSi₂

Refernces

• 1、 -. "IMPROVED SYNTHESIS OF CAPURAMYCIN AND ITS ANALOGUES". Page/Page column 37-38. . Retrieved 2015/03/13.
• 2、 Kurosu, Michio,Li, Kai,Crick, Dean C.. "Concise synthesis of capuramycin". supporting information; experimental part. p. 2393 - 2396. Retrieved 2009/10/23.