191165-23-8

Basic information

• Product Name: (2R,3S,4R,5R)-2,3,4,6-Tetrakis-benzyloxy-5-hydroxy-hexanoic acid [3-(4-methoxy-benzyloxy)-propyl]-amide
• Synonyms: (2R,3S,4R,5R)-2,3,4,6-Tetrakis-benzyloxy-5-hydroxy-hexanoic acid [3-(4-methoxy-benzyloxy)-propyl]-amide
• CAS NO: 191165-23-8
• Molecular Weight: 733.902
• Mol File: 191165-23-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,3S,4R,5R)-2,3,4,6-Tetrakis-benzyloxy-5-hydroxy-hexanoic acid [3-(4-methoxy-benzyloxy)-propyl]-amide(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,4R,5R)-2,3,4,6-Tetrakis-benzyloxy-5-hydroxy-hexanoic acid [3-(4-methoxy-benzyloxy)-propyl]-amide(191165-23-8)
• EPA Substance Registry System: (2R,3S,4R,5R)-2,3,4,6-Tetrakis-benzyloxy-5-hydroxy-hexanoic acid [3-(4-methoxy-benzyloxy)-propyl]-amide(191165-23-8)

Safety Data

• Hazardous Substances Data: 191165-23-8(Hazardous Substances Data)

Upstream product

• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 
• 191165-22-7 3-((4-methoxybenzyl)oxy)propan-1-amine 

Relevant articles and documents

An efficient activation of the hydroxyl function by (diethylamino)sulfur trifluoride (DAST): preparation of chiral polyoxygenated tetrahydrofurans by stereoselective benzyloxy group participation

Based on an intramolecular benzyloxy or amide group participation, two sets of experimental conditions have been established for the preparation of cis/trans tetrahydrofurans 6 or lactone 8 from sugar-derived open-chain hydroxylated precursors 4.These include: (1) a two-step mesylation-cyclization promoted by LiOH/THF-H2O or NaI/CH3CN at reflux; or (2) a one-step cyclization mediated by (diethylamino)sulfur trifluoride (DAST) at -78 deg C in CH2Cl2.The scope and limitations of these cyclizations are described particularly in relation to a stereoselective synthesis of highly oxygenated chiral tetrahydrofurans.Molecular modeling studies tentatively rationalized our experimental cyclization results affording five-membered versus six-membered heterocycles starting from different precursors. - Keywords: polyoxygenated tetrahydrofuran; (diethylamino)sulfur trifluoride (DAST); benzyl group participation; amide group participation; L-gulonolactone; differentially protected 1,4-diol