Lactimidomycin

Base Information

• Chemical Name: Lactimidomycin
• CAS No.: 134869-15-1
• Molecular Formula: C26H35 N O6
• Molecular Weight: 457.567
• ChEMBL ID: CHEMBL1221911
• DSSTox Substance ID: DTXSID401028055
• Metabolomics Workbench ID: 108484
• Nikkaji Number: J493.002I
• Wikidata: Q105203446
• Wikipedia: Lactimidomycin
• Mol file: 134869-15-1.mol

Synonyms:2,6-piperidinedione, 4-(2-hydroxy-5-methyl-7-(3-methyl-12-oxooxacyclododeca-4,6,10-trien-2-yl)-4-oxo-6-octenyl)-;4-(2-hydroxy-5-methyl-7-(3-methyl-12-oxooxacyclododeca-4,6,10-trien-2-yl)-4-oxo-6-octenyl)-2,6-piperidinedione;lactimidomycin

Chemical Property of Lactimidomycin

Chemical Property:

• Vapor Pressure: 6.04E-23mmHg at 25°C
• Boiling Point: 704.6°Cat760mmHg
• Flash Point: 379.9°C
• PSA: 113.26000
• Density: 1.115g/cm³
• LogP: 3.61800
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 457.24643784
• Heavy Atom Count: 33
• Complexity: 837

Purity/Quality:

99%, ^*data from raw suppliers

Lactimidomycin - CAS 134869-15-1 - Calbiochem ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C=CC=CCCC=CC(=O)OC1C(=CC(C)C(=O)CC(CC2CC(=O)NC(=O)C2)O)C
• Isomeric SMILES: C[C@H]1/C=C\C=C\CC/C=C/C(=O)O[C@H]1/C(=C/[C@H](C)C(=O)C[C@@H](CC2CC(=O)NC(=O)C2)O)/C

Technology Process of Lactimidomycin

There total 26 articles about Lactimidomycin 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:

C29H43NO6Si (1440545-78-7) → lactimidomycin (134869-15-1)

Guidance literature:

With pyridine hydrogenfluoride; In tetrahydrofuran; at 0 - 20 ℃; for 2.5h; Inert atmosphere;

DOI:10.1021/ol401186f

Reference yield:

(R)-4-benzyl-3-((2R,3R,6S,7R,E)-7-(((tert-butyl)dimethylsilyl)oxy)-2,4,6-trimethyl-3-((trimethylsilyl)oxy)oct-4-enoyl)oxazolidin-2-one (1440545-59-4) → lactimidomycin (134869-15-1)

Guidance literature:

Multi-step reaction with 13 steps

1.1: n-butyllithium / tetrahydrofuran / -20 °C / Inert atmosphere

1.2: 2 h / -20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / dichloromethane / 0.67 h / -78 °C / Inert atmosphere

3.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.17 h / Inert atmosphere; Sonication

3.2: 1.25 h / -78 - 20 °C / Inert atmosphere

4.1: toluene-4-sulfonic acid / dichloromethane; methanol / 0.67 h / 0 °C / Inert atmosphere

5.1: dmap; pyridine / tetrahydrofuran / 1.58 h / 0 - 20 °C / Inert atmosphere

6.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium hydroxide / tetrahydrofuran; water / 18 h / Inert atmosphere

7.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 2.75 h / 20 °C / Inert atmosphere

8.1: triethylamine; N,N,N,N,-tetramethylethylenediamine; zinc trifluoromethanesulfonate / tetrahydrofuran / 19 h / Inert atmosphere

9.1: pyridine hydrogenfluoride / tetrahydrofuran / 3.75 h / 0 - 20 °C / Inert atmosphere

10.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 1.58 h / 0 - 20 °C / Inert atmosphere

11.1: triethylamine; lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

12.1: C₂₄H₂₁BN₂O₄S / 22 h / -78 °C / Molecular sieve; Inert atmosphere

13.1: pyridine hydrogenfluoride / tetrahydrofuran / 2.5 h / 0 - 20 °C / Inert atmosphere

With pyridine; dmap; n-butyllithium; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; N,N,N,N,-tetramethylethylenediamine; C₂₄H₂₁BN₂O₄S; sodium hexamethyldisilazane; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; pyridine hydrogenfluoride; triethylamine; sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; 6.1: |Suzuki Coupling / 7.1: |Dess-Martin Oxidation / 8.1: |Horner-Wadsworth-Emmons Olefination / 12.1: |Mukaiyama Aldol Addition;

DOI:10.1021/ol401186f

Reference yield:

(2R,3R,6S,7R,E)-S-ethyl_7-(((tert-butyl)dimethylsilyl)oxy)-2,4,6-trimethyl-3-((trimethylsilyl)oxy)oct-4-enethioate (1440545-73-2) → lactimidomycin (134869-15-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: diisobutylaluminium hydride / dichloromethane / 0.67 h / -78 °C / Inert atmosphere

2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.17 h / Inert atmosphere; Sonication

2.2: 1.25 h / -78 - 20 °C / Inert atmosphere

3.1: toluene-4-sulfonic acid / dichloromethane; methanol / 0.67 h / 0 °C / Inert atmosphere

4.1: dmap; pyridine / tetrahydrofuran / 1.58 h / 0 - 20 °C / Inert atmosphere

5.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium hydroxide / tetrahydrofuran; water / 18 h / Inert atmosphere

6.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 2.75 h / 20 °C / Inert atmosphere

7.1: triethylamine; N,N,N,N,-tetramethylethylenediamine; zinc trifluoromethanesulfonate / tetrahydrofuran / 19 h / Inert atmosphere

8.1: pyridine hydrogenfluoride / tetrahydrofuran / 3.75 h / 0 - 20 °C / Inert atmosphere

9.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 1.58 h / 0 - 20 °C / Inert atmosphere

10.1: triethylamine; lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

11.1: C₂₄H₂₁BN₂O₄S / 22 h / -78 °C / Molecular sieve; Inert atmosphere

12.1: pyridine hydrogenfluoride / tetrahydrofuran / 2.5 h / 0 - 20 °C / Inert atmosphere

With pyridine; dmap; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; N,N,N,N,-tetramethylethylenediamine; C₂₄H₂₁BN₂O₄S; sodium hexamethyldisilazane; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; pyridine hydrogenfluoride; triethylamine; sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; 5.1: |Suzuki Coupling / 6.1: |Dess-Martin Oxidation / 7.1: |Horner-Wadsworth-Emmons Olefination / 11.1: |Mukaiyama Aldol Addition;

DOI:10.1021/ol401186f

upstream raw materials:

(R)-4-benzyl-3-((2R,3R,6S,7R,E)-7-(((tert-butyl)dimethylsilyl)oxy)-2,4,6-trimethyl-3-((trimethylsilyl)oxy)oct-4-enoyl)oxazolidin-2-one

(2R,3R,6S,7R,E)-S-ethyl_7-(((tert-butyl)dimethylsilyl)oxy)-2,4,6-trimethyl-3-((trimethylsilyl)oxy)oct-4-enethioate

(2R,3R,6S,7R,E)-7-(((tert-butyl)dimethylsilyl)oxy)-2,4,6-trimethyl-3-((trimethylsilyl)oxy)oct-4-enal

(4R,7S,8R,E)-4-((S,Z)-4-iodobut-3-en-2-yl)-2,2,5,7,8,10,10,11,11-nonamethyl-3,9-dioxa-2,10-disiladodec-5-ene

Refernces

• 1、 Micoine, Kevin,Fuerstner, Alois. "Concise total synthesis of the potent translation and cell migration inhibitor lactimidomycin". . p. 14064 - 14066. Retrieved 2010.