1449329-21-8

Basic information

• Product Name: benzyl ((1R,2R,3R,5R)-3-((S)-1-((tert-butyldimethylsilyl)oxy)ethyl)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-3-(3,3-dimethylureido)-4-oxo-6-oxabicyclo[3.1.0] hexan2-yl)carbamate
• Synonyms: benzyl ((1R,2R,3R,5R)-3-((S)-1-((tert-butyldimethylsilyl)oxy)ethyl)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-3-(3,3-dimethylureido)-4-oxo-6-oxabicyclo[3.1.0] hexan2-yl)carbamate
• CAS NO: 1449329-21-8
• Molecular Weight: 760.09
• Mol File: 1449329-21-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: benzyl ((1R,2R,3R,5R)-3-((S)-1-((tert-butyldimethylsilyl)oxy)ethyl)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-3-(3,3-dimethylureido)-4-oxo-6-oxabicyclo[3.1.0] hexan2-yl)carbamate(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl ((1R,2R,3R,5R)-3-((S)-1-((tert-butyldimethylsilyl)oxy)ethyl)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-3-(3,3-dimethylureido)-4-oxo-6-oxabicyclo[3.1.0] hexan2-yl)carbamate(1449329-21-8)
• EPA Substance Registry System: benzyl ((1R,2R,3R,5R)-3-((S)-1-((tert-butyldimethylsilyl)oxy)ethyl)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-3-(3,3-dimethylureido)-4-oxo-6-oxabicyclo[3.1.0] hexan2-yl)carbamate(1449329-21-8)

Safety Data

• Hazardous Substances Data: 1449329-21-8(Hazardous Substances Data)

Upstream product

• 69739-34-0 t-butyldimethylsiyl triflate 
• 29397-21-5 Diacetyldiazomethan 
• 123-54-6 acetylacetone 
• 1449329-18-3 C₂₅H₄₁N₃O₇Si 
• 941602-18-2 [(E)-3-Phenyl-prop-2-en-(E)-ylidene]-carbamic acid benzyl ester 
• 1449329-20-7 benzyl ((1R,2R,3R,5R)-3-((S)-1-((tert-butyldimethylsilyl)oxy)ethyl)-3-(3,3-dimethylureido)-5-(hydroxymethyl)-4-oxo-6-oxabicyclo[3.1.0]hexan-2-yl)carbamate 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 1449329-12-7 3-(2,4-dioxopentan-3-yl)-1,1-dimethylurea 

Downstream Products

• 1449329-24-1 benzyl ((1S,2R,3R,4S,5S)-5-((3-acetylphenyl)amino)-2-(3,3-dimethylureido)-3,4-dihydroxy-2-((S)-1-hydroxyethyl)-4-(hydroxymethyl)-3-methylcyclopentyl)carbamate 
• 1449329-25-2 ((1S,2R,3R,4S,5S)-5-((3-acetylphenyl)amino)-4-(((benzyloxy)carbonyl)amino)-3-(3,3-dimethylureido)-1,2-dihydroxy-3-((S)-1-hydroxyethyl)-2-methylcyclopentyl)methyl 2-hydroxy-6-methylbenzoate 
• 23668-11-3 pactamycin 
• 1449329-22-9 benzyl ((1R,2R,3R,4R,5R)-3-((S)-1-((tert-butyldimethylsilyl)oxy)ethyl)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-3-(3,3-dimethylureido)-4-hydroxy-4-methyl-6-oxabicyclo[3.1.0]hexan-2-yl)carbamate 

Relevant articles and documents

SYNTHETIC ROUTE TO PACTAMYCIN AND PACTAMYCIN ANALOGS

Methods and intermediates useful for making compounds of Formula (I) are described, including a general method of making an alpha, beta-diamino ketone by reacting an imine with a 2-amino-substituted 1,3-dicarbonyl in a Mannich addition reaction to produce said alpha,beta-diamino ketone.

Enantioselective synthesis of pactamycin, a complex antitumor antibiotic

Medicinal application of many complex natural products is precluded by the impracticality of their chemical synthesis. Pactamycin, the most structurally intricate aminocyclopentitol antibiotic, displays potent antiproliferative properties across multiple phylogenetic domains, but it is highly cytotoxic. A limited number of analogs produced by genetic engineering technologies show reduced cytotoxicity against mammalian cells, renewing promise for therapeutic applications. For decades, an efficient synthesis of pactamycin amenable to analog derivatizations has eluded researchers. Here, we present a short asymmetric total synthesis of pactamycin. An enantioselective Mannich reaction and symmetry-breaking reduction sequence was designed to enable assembly of the entire carbon core skeleton in under five steps and control critical three-dimensional (stereochemical) functional group relationships. This modular route totals 15 steps and is immediately amenable for structural analog synthesis.