143669-25-4

Basic information

• Product Name: (1R,4S,5S)-4-heptadecyl-3,6,8-trioxabicyclo<3.2.1>octane
• CAS NO: 143669-25-4
• Molecular Weight: 354.574
• Mol File: 143669-25-4.mol

Chemical Properties

• CAS DataBase Reference: (1R,4S,5S)-4-heptadecyl-3,6,8-trioxabicyclo<3.2.1>octane(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,4S,5S)-4-heptadecyl-3,6,8-trioxabicyclo<3.2.1>octane(143669-25-4)
• EPA Substance Registry System: (1R,4S,5S)-4-heptadecyl-3,6,8-trioxabicyclo<3.2.1>octane(143669-25-4)

Safety Data

• Hazardous Substances Data: 143669-25-4(Hazardous Substances Data)

Upstream product

• 143669-21-0 (4R)-2-(1'-bromooctadecyl)-4-(hydroxymethyl)-1,3-dioxolane 
• 143669-21-0 (2S,4R)-2-(1'-bromooctadecyl)-4-hydroxymethyl-1,3-dioxolane 

Relevant articles and documents

Single crystal X-ray structures of the two 4-heptadecyl derivatives of (1R,5S)-3,6,8-trioxabicyclooctane

The single crystal structures of the two diastereomeric 4-heptadecyl derivatives of (1R,5S)-3,6,8-trioxabicyclooctane have been determined by X-ray diffraction to be (1R,4R,5S)-heptadecyl-3,6,8-trioxabicyclooctane (I) and (1R,4S,5S)-4-heptadecylooctane (II), respectively, which have an exo or axial 4-heptadecyl group, and an endo or equatorial 4-heptadecyl group, respectively.The structures of I and II had been suggested by their phase-sensitive 2D NOESY 1H-NMR spectra, but are now established unambiguously.These optically pure non-ionic lipid-like amphipathic molecules (I and II) represent the first 3,6,8-trioxabicyclooctanes for which single crystal structures have been solved.Crystals of both isomer I and isomer II were orthorhombic with space group P212121 and had unit cell dimensions of a = 9.586, b = 43.14, c = 5.289 Angstroem, and a = 7.34, b = 51.8, c = 5.636 Angstroem, respectively.The structures of I and II were both solved by using direct methods to R = 0.045 and R = 0.086, respectively.Both I and II pack in stacked bilayers with interdigitating and tilting hydrocarbon chains.The molecular and hydrocarbon cross sections are I: S = 50.70 Angstroem2, Σ = 19.00 Angstroem2 ; and II: S = 41.37 Angstroem2, Σ = 18.26 Angstroem2.Keywords: (1R,4R,5S)-4-heptadecyl-3,6,8-trioxabicyclooctane; (1R,4S,5S)-4-heptadecyl-3,6,8-trioxabicyclooctane; X-ray; Crystal structure; Molecular packing; Nonionic amphiphile

Syntheses of All Four Stereoisomers Which Are Conformationally Constrained 1,4-Dioxanyl Analogs of the Antineoplastic Ether Lipid ET-18-OCH3

The syntheses of each of the four nearly optically pure stereoisomers of oxy>phosphocholine (2,3,2',3') were performed by two parallel divergent sequences.Phosphocholines 2 and 3 were prepared via the corresponding 5-heptadecyl-2-(hydroxymethyl)-1,4-dioxanes 21 and 23, respectively, from the completely regiospecific mixed-hydride reductions of (1R,4S,5S)-4-heptadecyl-3,6,8-trioxabicyclooctane (19) and (1R,4R,5S)-4-heptadecyl-3,6,8-trioxabicyclooctane (20), respectively.The two 4-heptadecyl-3,6,8-trioxabicyclooctanes 19 and 20 were the two separable products from an intramolecular cyclization reaction.By a parallel divergent sequence from the enantiomeric starting material, 3-O-benzyl-sn-glycerol (16'), the other two diastereomeric oxy>phosphocholines 2' and 3' were prepared.These four monocyclic oxy>phosphocholines (2,3,2',3') are conformationally constrained analogs of the antineoplastic and immunomodulatory ether lipid rac-2-O-methyl-1-O-octadecylglycero-3-phosphocholine (rac-1) (rac-ET-18-OCH3, rac-Edelfosine).