S-[6-[[5-[5-(ethylamino)-4-methoxyoxan-2-yl]oxy-4-hydroxy-6-[[9-hydroxy-12-(methoxycarbonylamino)-13-[2-(methyltrisulfanyl)ethylidene]-11-oxo-2-bicyclo[7.3.1]trideca-1(12),5-dien-3,7-diynyl]oxy]-2-methyloxan-3-yl]amino]oxy-4-hydroxy-2-methyloxan-3-yl] 4-(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy-5-iodo-2,3-dimethoxy-6-methylbenzenecarbothioate

Base Information

• Chemical Name: S-[6-[[5-[5-(ethylamino)-4-methoxyoxan-2-yl]oxy-4-hydroxy-6-[[9-hydroxy-12-(methoxycarbonylamino)-13-[2-(methyltrisulfanyl)ethylidene]-11-oxo-2-bicyclo[7.3.1]trideca-1(12),5-dien-3,7-diynyl]oxy]-2-methyloxan-3-yl]amino]oxy-4-hydroxy-2-methyloxan-3-yl] 4-(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy-5-iodo-2,3-dimethoxy-6-methylbenzenecarbothioate
• CAS No.: 108212-75-5
• Molecular Formula: C₅₅H₇₄IN₃O₂₁S₄
• Molecular Weight: 1368.37
• European Community (EC) Number: 813-745-9
• Wikipedia: Calicheamicin
• Mol file: 108212-75-5.mol

Synonyms:calicheamicin gamma(1)I;calichemicin gamma1

Chemical Property of S-[6-[[5-[5-(ethylamino)-4-methoxyoxan-2-yl]oxy-4-hydroxy-6-[[9-hydroxy-12-(methoxycarbonylamino)-13-[2-(methyltrisulfanyl)ethylidene]-11-oxo-2-bicyclo[7.3.1]trideca-1(12),5-dien-3,7-diynyl]oxy]-2-methyloxan-3-yl]amino]oxy-4-hydroxy-2-methyloxan-3-yl] 4-(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy-5-iodo-2,3-dimethoxy-6-methylbenzenecarbothioate

Chemical Property:

• Refractive Index: 1.662
• Boiling Point: °Cat760mmHg
• PKA: 7.13±0.60(Predicted)
• Flash Point: °C
• PSA: 409.64000
• Density: 1.57g/cm³
• LogP: 4.36950
• XLogP3: 2
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 27
• Rotatable Bond Count: 24
• Exact Mass: 1367.27424
• Heavy Atom Count: 84
• Complexity: 2500

Purity/Quality:

98%,99%, ^*data from raw suppliers

Calicheamicin >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCNC1COC(CC1OC)OC2C(C(C(OC2OC3C#CC=CC#CC4(CC(=O)C(=C3C4=CCSSSC)NC(=O)OC)O)C)NOC5CC(C(C(O5)C)SC(=O)C6=C(C(=C(C(=C6OC)OC)OC7C(C(C(C(O7)C)O)OC)O)I)C)O)O
• description: Calicheamicins are a series of enediyne antitumor antibiotics originally isolated from the bacterium Micromonospora echinospora. They exert high cytotoxicity and have been applied in tumor therapies for over a decade-- a CD33 antigen-targeted immuno-conjugate: N-acetyl dimethyl hydrazide calicheamicin, was developed as a targeted therapy for non-solid tumor cancer acute myeloid leukemia (AML). Calicheamicin has several derivatives with different chemical modifications, among which γ1 is the most well-characterized. Calicheamicin γ1 contains an aglycon consisting of a bicycle tridec-9-ene-2,6-diyne system with a labile methyl trisul?de group and an aryltetrasaccharide chain. Calicheamicins also contain enediyne moieties that are structurally similar to other enediynes, such as esperamicins, neocarzinostatin, and kedarcidin, etc. After reduction by cellular thiols, the calicheamicin enediyne moieties rearrange to produce a 1, 4-benzenoid diradical.
• Uses: Calicheamicin, also known as Calicheamicin gamma(1,I) or Calichemicin gamma1, is an potent enediyne antitumor antibiotics derived from the bacterium Micromonospora echinospora. Calicheamicin targets DNA and cause strand scission. Calicheamicin binds with DNA in the minor groove, wherein it then undergos a reaction analogous to the Bergman cyclization to generate a diradical species. This diradical, 1,4-didehydrobenzene, then abstracts hydrogen atoms from the deoxyribose (sugar) backbone of DNA, which ultimately leads to strand scission. The specificity of binding of calicheamicin to the minor groove of DNA is due to the aryltetrasaccharide group of the molecule. Calicheamicins are a class of enediyne antitumor antibiotics derived from the bacterium Micromonospora echinospora, The main component is calicheamicin γ1. It has strong anti-Gram-positive bacteria activity and anti-tumor effect.
• Description: Calicheamicin gamma1 is an enediyne antitumor antibiotic that binds with DNA in the minor groove and is derived from the bacterium Micromonospora echinospora.

Technology Process of S-[6-[[5-[5-(ethylamino)-4-methoxyoxan-2-yl]oxy-4-hydroxy-6-[[9-hydroxy-12-(methoxycarbonylamino)-13-[2-(methyltrisulfanyl)ethylidene]-11-oxo-2-bicyclo[7.3.1]trideca-1(12),5-dien-3,7-diynyl]oxy]-2-methyloxan-3-yl]amino]oxy-4-hydroxy-2-methyloxan-3-yl] 4-(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy-5-iodo-2,3-dimethoxy-6-methylbenzenecarbothioate

There total 3 articles about S-[6-[[5-[5-(ethylamino)-4-methoxyoxan-2-yl]oxy-4-hydroxy-6-[[9-hydroxy-12-(methoxycarbonylamino)-13-[2-(methyltrisulfanyl)ethylidene]-11-oxo-2-bicyclo[7.3.1]trideca-1(12),5-dien-3,7-diynyl]oxy]-2-methyloxan-3-yl]amino]oxy-4-hydroxy-2-methyloxan-3-yl] 4-(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy-5-iodo-2,3-dimethoxy-6-methylbenzenecarbothioate 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: 90.0%

C70H84IN3O23S4 (144668-44-0) → calicheamicin γ1I (108212-75-5)

Guidance literature:

With diethylamine; In tetrahydrofuran; water; at 25 ℃; for 1.5h;

DOI:10.1021/ja00051a063

Reference yield:

C96H142IN3O26S4Si4 (158862-55-6) → calicheamicin γ1I (108212-75-5)

Guidance literature:

With camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; Yield given. Multistep reaction; 1.) THF, 25 deg C, 96 h, 2.) THF, 0 deg C, 15 min;

Reference yield:

C96H142IN3O26S4Si4 → calicheamicin γ1I (108212-75-5)

Guidance literature:

With camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; Yield given. Multistep reaction; 1.) THF, H₂O, 2.) THF;

DOI:10.1021/jo951560x

upstream raw materials:

C₇₀H₈₄IN₃O₂₃S₄

C₉₆H₁₄₂IN₃O₂₆S₄Si₄

Downstream raw materials:

C₁₀₈H₁₄₂I₂N₆O₄₂S₅

C₅₄H₇₄IN₃O₂₁S₂

triphenylphosphine sulfide

Triphenylphosphine oxide

Refernces

• 1、 Hitchcock, Stephen A.,Chu-Moyer, Margaret Y.,Boyer, Serge H.,Olson, Steven H.,Danishefsky, Samuel J.. "A remarkable glycosylation reaction: The total synthesis of calicheamicin γ1I". . p. 5750 - 5756. Retrieved 2007/10/02.
• 2、 Nicolaou,Hummel,Nakada,Shibayama,Pitsinos,Saimoto,Mizuno,Baldenius,Smith. "Total synthesis of calicheamicin γ1(I). 3. The final stages". . p. 7625 - 7635. Retrieved 2007/10/02.