11107B

Base Information

• Chemical Name: 11107B
• CAS No.: 445493-23-2
• Molecular Formula: C30H48O8
• Molecular Weight: 536.706
• DSSTox Substance ID: DTXSID701098499
• Metabolomics Workbench ID: 110372
• Nikkaji Number: J2.518.852G
• Pharos Ligand ID: 5HS9DTFZT51T
• Wikidata: Q76507757
• Mol file: 445493-23-2.mol

Synonyms:11107AD;11107B;PLADIENOLIDE B

Chemical Property of 11107B

Chemical Property:

• PSA: 125.82000
• LogP: 4.02110
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 10
• Exact Mass: 536.33491849
• Heavy Atom Count: 38
• Complexity: 880

Purity/Quality:

97% ^*data from raw suppliers

PladienolideB ≥95%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC(C(C)C1C(O1)CC(C)C=CC=C(C)C2C(C=CC(C(CCC(CC(=O)O2)O)(C)O)OC(=O)C)C)O
• Isomeric SMILES: CC[C@@H]([C@@H](C)[C@@H]1[C@H](O1)C[C@H](C)/C=C/C=C(\C)/[C@@H]2[C@H](/C=C/[C@@H]([C@](CC[C@H](CC(=O)O2)O)(C)O)OC(=O)C)C)O
• Uses: Pladienolide B is the major analogue of a family of macrocyclic lactones isolated from Streptomyces platensis. Pladienolide B is a highly potent inhibitor of both hypoxia signals and cancer cell proliferation. Pladienolide B binds to SF3b complex blocking the spliceosome. Pladienolide B is a potent cancer cell growth inhibitor that targets the SF3B1 subunit of the spliceosome.

Technology Process of 11107B

There total 95 articles about 11107B 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: 87.0%

(2S,3S,6S,7R,10R,E)-7,10-dihydroxy-2-((E)-1-iodoprop-1-en-2-yl)-3,7-dimethyl-12-oxooxacyclododec-4-en-6-yl acetate (1403584-93-9) + (2R,3S)-2-{(2R,3R)-3-[(S,E)-2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-yl]oxiran-2-yl}pentan-3-ol → (2S,3S,6S,7R,10R,E)-7,10-dihydroxy-2-{(S,2E,4E)-7-[(2R,3R)-3-{(2R,3S)-3-hydroxypentan-2-yl}oxiran-2-yl]-6-methylhepta-2,4-dien-2-yl}-3,7-dimethyl-12-oxooxacyclododec-4-en-6-yl acetate (445493-23-2)

Guidance literature:

(2S,3S,6S,7R,10R,E)-7,10-dihydroxy-2-((E)-1-iodoprop-1-en-2-yl)-3,7-dimethyl-12-oxooxacyclododec-4-en-6-yl acetate; (2R,3S)-2-{(2R,3R)-3-[(S,E)-2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-yl]oxiran-2-yl}pentan-3-ol; With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; water; at 22 ℃; for 3h; Inert atmosphere;

With ammonium tetramethylenedithiocarbamate; In tetrahydrofuran; water; at 22 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jacs.1c01135

Reference yield: 82.0%

(4R,7R,8S,11S,12S,E)-4,7,8-trihydroxy-12-{(S,2E,4E)-7-[(2R,3R)-3-{(2R,3S)-3-hydroxypentan-2-yl}oxiran-2-yl]-6-methylhepta-2,4-dien-2-yl}-7,11-dimethyloxacyclododec-9-en-2-one + acetic anhydride (108-24-7) → (2S,3S,6S,7R,10R,E)-7,10-dihydroxy-2-{(S,2E,4E)-7-[(2R,3R)-3-{(2R,3S)-3-hydroxypentan-2-yl}oxiran-2-yl]-6-methylhepta-2,4-dien-2-yl}-3,7-dimethyl-12-oxooxacyclododec-4-en-6-yl acetate (445493-23-2)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1002/anie.200604997

Reference yield: 68.0%

(2S,3S,6S,7R,10R,E)-7,10-dihydroxy-2-((E)-1-iodoprop-1-en-2-yl)-3,7-dimethyl-12-oxooxacyclododec-4-en-6-yl acetate (1403584-93-9) + (2R,3S)-2-{(2R,3R)-3-[(S)-2-methylbut-3-yn-1-yl]oxiran-2-yl}pentan-3-ol (1446121-22-7) → (2S,3S,6S,7R,10R,E)-7,10-dihydroxy-2-{(S,2E,4E)-7-[(2R,3R)-3-{(2R,3S)-3-hydroxypentan-2-yl}oxiran-2-yl]-6-methylhepta-2,4-dien-2-yl}-3,7-dimethyl-12-oxooxacyclododec-4-en-6-yl acetate (445493-23-2)

Guidance literature:

(2R,3S)-2-{(2R,3R)-3-[(S)-2-methylbut-3-yn-1-yl]oxiran-2-yl}pentan-3-ol; With bis-triphenylphosphine-palladium(II) chloride; tri-n-butyl-tin hydride; In tetrahydrofuran; at 0 - 20 ℃; for 0.416667h;

(2S,3S,6S,7R,10R,E)-7,10-dihydroxy-2-((E)-1-iodoprop-1-en-2-yl)-3,7-dimethyl-12-oxooxacyclododec-4-en-6-yl acetate; With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; triphenyl-arsane; lithium chloride; In 1-methyl-pyrrolidin-2-one; at 20 ℃; for 48h;

DOI:10.1021/ol401458d

upstream raw materials:

acetic anhydride

(6R,7S)-tert-butyl 6-hydroxy-7-((4-methoxybenzyl)oxy)-3-oxonon-8-enoate

(6R,7S)-tert-butyl 7-((4-methoxybenzyl)oxy)-3-oxo-6-((triethylsilyl)oxy)non-8-enoate

(3R,6R,7S)-tert-butyl 3-hydroxy-7-((4-methoxybenzyl)oxy)-6-((triethylsilyl)oxy)non-8-enoate

Downstream raw materials:

C₅₀H₆₂F₆O₁₂