CID 127719

Base Information

• Chemical Name: CID 127719
• CAS No.: 100940-65-6
• Molecular Formula: C₆₀H₇₆N₁₂O₁₆
• Molecular Weight: 1221.33
• Hs Code.: 29419000
• Mol file: 100940-65-6.mol

Synonyms:sandramycin

Chemical Property of CID 127719

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1518.4°C at 760 mmHg
• Flash Point: 872.1°C
• PSA: 357.10000
• Density: 1.42g/cm³
• LogP: 1.13540
• Solubility.: Soluble in DMSO
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 18
• Rotatable Bond Count: 6
• Exact Mass: 1220.55022438
• Heavy Atom Count: 88
• Complexity: 2400

Purity/Quality:

97% ^*data from raw suppliers

Sandramycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1C(=O)OCC(C(=O)N2CCCCC2C(=O)NCC(=O)N(CC(=O)N(C(C(=O)OCC(C(=O)N3CCCCC3C(=O)NCC(=O)N(CC(=O)N1C)C)NC(=O)C4=NC5=CC=CC=C5C=C4O)C(C)C)C)C)NC(=O)C6=NC7=CC=CC=C7C=C6O
• General Description: Sandramycin is a potent antitumor antibiotic known for its high-affinity, bifunctional DNA intercalation properties, exhibiting binding selectivity and the ability to induce unwinding and rewinding of supercoiled DNA at lower concentrations compared to similar agents like luzopeptin A. Its structure and stereochemistry have been confirmed through total synthesis, paving the way for the development of analogs with tailored DNA-binding capabilities.

Technology Process of CID 127719

There total 27 articles about CID 127719 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: 78.0%

sandramycin bis-O-benzyl ether → sandramycin (100940-65-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; at 25 ℃; for 12h;

DOI:10.1021/ja00077a082

Reference yield:

Methyl 3-hydroxyquinoline-2-carboxylate (15462-45-0) + (3R,7S,16S,23R,27S,36S)-3,23-Diamino-7,27-diisopropyl-8,11,28,31-tetramethyl-5,25-dioxa-1,8,11,14,21,28,31,34-octaaza-tricyclo[34.4.0.016,21]tetracontane-2,6,9,12,15,22,26,29,32,35-decaone → sandramycin (100940-65-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 24h; Inert atmosphere;

DOI:10.1021/ol403319m

Reference yield:

(S)-5-azido-2-triisopropylsilyloxy-1-pentanol (1515605-77-2) → sandramycin (100940-65-6)

Guidance literature:

Multi-step reaction with 11 steps

1: triethylamine; sulfur trioxide pyridine complex; dimethyl sulfoxide / 0.5 h / 20 °C / Inert atmosphere

2: triethylphosphine / toluene; tetrahydrofuran / 30 h / 0 - 20 °C / Inert atmosphere

3: triethylphosphine / toluene / 48 h / 70 °C / Inert atmosphere

4: dmap; triethylamine / acetonitrile / 12 h / 20 °C / Inert atmosphere

5: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / 2,2,2-trifluoroethanol / 1 h / 78 °C / Inert atmosphere

6: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere

7: sodium hydrogencarbonate; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one / N,N-dimethyl-formamide; dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere

8: hydrogenchloride / 1,4-dioxane / 0.5 h / Inert atmosphere

9: sodium hydrogencarbonate; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one / N,N-dimethyl-formamide; dichloromethane / 48 h / 0 - 20 °C / Inert atmosphere

10: 10% palladium hydroxide on charcoal; hydrogen / methanol / 3 h / 20 °C

11: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 24 h / 0 - 20 °C / Inert atmosphere

With hydrogenchloride; dmap; 2,2'-azobis(isobutyronitrile); 10% palladium hydroxide on charcoal; hydrogen; tri-n-butyl-tin hydride; sulfur trioxide pyridine complex; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; triethylphosphine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; 2,2,2-trifluoroethanol; N,N-dimethyl-formamide; toluene; acetonitrile; 3: |Ugi Condensation;

DOI:10.1021/ol403319m

upstream raw materials:

(S)-5-azido-2-triisopropylsilyloxy-1-pentanol

N-Cbz-D-Ser[N-Me-Boc-Val]-(S)-β-L-triisopropylsilyloxy-Pip-Gly-Sar allyl ester

N-Cbz-D-Ser[N-Me-Boc-Val]-L-Pip-Gly-Sar allyl ester

N-Cbz-D-Ser[N-Me-Boc-Val]-L-Pip-Gly-Sar-OH

Refernces

(-)-sandramycin: Total synthesis and preliminary DNA binding properties

10.1021/ja00077a082

The research focuses on the total synthesis of (-)-sandramycin, a potent antitumor antibiotic, and an investigation into its preliminary DNA binding properties. The purpose of this study was to confirm the structure and absolute stereochemistry of sandramycin and to report on its high-affinity, bifunctional intercalation with DNA. The researchers achieved the first total synthesis of a member of this class of naturally occurring agents, which could lead to the development of analogs with modified intercalation capabilities. Key chemicals used in the synthesis process included BOC-Gly-Sar-OH, D-N-Me-val-oCH2l, DCC, DMAP, EDCI, HOBt, NaHCO3, and various other reagents for coupling reactions, deprotection steps, and cyclization. The conclusions drawn from the study indicated that (-)-sandramycin possesses a binding constant comparable to luzopeptin A, binds with higher selectivity, and induces the unwinding of negatively supercoiled DNA and its rewinding at lower agent concentrations than luzopeptin A.

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