171252-88-3

Upstream product

• 171252-92-9 (3R,4S,5S)-4,5-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)-1-cyclohexene-3,4,5-triol 
• 183268-55-5 (1R,2R,3S,4S,5S)-3-O-benzyl-5-((benzyloxy)methyl)-1,2-O-cyclohexylidenecyclohexane-1,2,3,4,5-pentol 
• 135735-90-9 (1R,2R,3S)-3-O-Benzyl-5-benzyloxymethyl-1,2-O-cyclohexylidene-cyclohex-4-en-1,2,3-triol 
• 171252-87-2 (1R,2S,3S,4S,5S)-4,5-di-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)-1,2-O-cyclohexylidenecyclohexane-1,2,3,4,5-pentol 

Downstream Products

• 171252-89-4 (1R,2S,3R,4S,5S)-4,5-di-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)-1-O-(trifluoromethanesulfonyl)cyclohexane-1,2,3,4,5-pentol 
• 171252-92-9 (3R,4S,5S)-4,5-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)-1-cyclohexene-3,4,5-triol 
• 171339-44-9 (1R,2S,3S,4S,5S)-4,5-di-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)-1,2-O,O-sulfonylcyclohexane-1,2,3,4,5-pentol 
• 183505-10-4 Acetic acid (1S,2S,3R,4R,5S)-2,4-diacetoxy-5-azido-3-benzyloxy-1-benzyloxymethyl-cyclohexyl ester 
• 183505-15-9 (1S,2S,3R,4S,5R)-5-Azido-3-benzyloxy-1-benzyloxymethyl-cyclohexane-1,2,4-triol 
• 183505-18-2 (1S,2S,3R,4R,5R)-5-Azido-3-benzyloxy-1-benzyloxymethyl-cyclohexane-1,2,4-triol 
• 183268-59-9 Acetic acid (1S,2S,3R,4S,5R)-2,4-diacetoxy-3-benzyloxy-1-benzyloxymethyl-5-trifluoromethanesulfonyloxy-cyclohexyl ester 
• 183268-63-5 Acetic acid (1S,2S,3R,4R,5R)-2,4-diacetoxy-3-benzyloxy-1-benzyloxymethyl-5-methanesulfonyloxy-cyclohexyl ester 
• 183268-66-8 Acetic acid (1S,5S,6S,7R,8R)-8-acetoxy-7-benzyloxy-5-benzyloxymethyl-3,3-dioxo-2,4-dioxa-3λ⁶-thia-bicyclo[3.3.1]non-6-yl ester 
• 183268-61-3 Acetic acid (1S,2S,3R,4S,5R)-2,4-diacetoxy-3-benzyloxy-1-benzyloxymethyl-5-hydroxy-cyclohexyl ester 
• 183268-67-9 Acetic acid (1S,2S,4R,5S,6R)-5-acetoxy-4-azido-6-benzyloxy-2-benzyloxymethyl-2-hydroxy-cyclohexyl ester 
• 183268-65-7 Acetic acid (1S,2S,4S,5S,6R)-5-acetoxy-6-benzyloxy-2-benzyloxymethyl-2,4-dihydroxy-cyclohexyl ester 
• 183268-58-8 (1S,2S,4R,5S,6R)-5-Azido-6-benzyloxy-2-benzyloxymethyl-cyclohexane-1,2,4-triol 
• 183505-11-5 (1S,2S,3R,4S,5R)-4-Amino-1-hydroxymethyl-cyclohexane-1,2,3,5-tetraol 

Relevant academic research and scientific papers

Facile syntheses of valiolamine and its diastereomers from (-)-quinic acid.1 nucleophilic substitution reactions of 5-(hydroxymethyl)cyclohexane-1,2,3,4,5-pentol

Valiolamine (1), 1-epi-valiolamine (2), 2-epi-valiolamine (3), (1R,2R)-valiolamine (4), and 2-amino regioisomer 17 have been prepared from (-)-quinic acid (6) in 14 (8.4% overall yield), 13 (9.0%), 15 (4.3%), 17 steps (2.5%), and 12 steps (13%), respectively. Charged nucleophilic ring-openings of cyclic sulfate (1R,2S,3S,4S,5S)-4,5-di-O-acetyl-3-O-benzyl-5-(benzyloxymethyl)-1,2-O,O- sulfonylcyclohexane-1,2,3,4,5-pentol (11) occurred regioselectively at C-2, whereas the corresponding ring-openings of its (1S,2R)-diastereomer 34 proceeded preponderantly at C-1. (1R,2S,3R,4S,5S)-2,4,5-Tri-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)-1-O- (trifluoromethanesulfonyl)cyclohexane-1,2,3,4,5-pentol (24) underwent novel internal displacement spontaneously to form (1S,2S,3R,4S,5S)-1,2,4-tri-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)cyclohexane- 1,2,3,4,5-pentol (25), whereas its 2-epimer was inert under the same conditions. Ruthenium-catalyzed dihydroxylation of alkene, (3R,4S,5S)-4,5-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)-1-cyclohexene-3,4,5- triol (31), gave the desired β-1,2-diol 32 in higher yield and stereoselectivity than the osmium tetraoxide protocol. The regioselectivity of charged nucleophilic ring-openings of cyclic sulfates 11, 34, and 38 is discussed.

Rhutenium-Catalyzed cis-Dihydroxylation of Alkenes: Scope and Limitations

Oxidative ruthenium catalysis (0.07 molequiv RuCl3*(H2O)3, 1.5 molequiv NaIO4, EtOAc/CH3CN/H2O 3:3:1), beyond the usual C-C bond cleavage to give dicarbonyls, have been shown to syn-dihydroxylate a wide range of alkenes (except for strained bicyclic alkenes, sterically hindered trisubstituted alkenes, and most tetrasubstituted alkenes) to give vicinal diols rapidly (within minutes) and efficiently.The minor products are the usual oxidative fission products, namely, ketones and aldehydes or carboxylic acids, and sometimes ketols.Longer reaction times lower the yields of most diols, probably owing to oxidative glycol cleavage.Reactions with substrates containing one or more electron-withdrawing groups in conjugation with or adjacent to the alkene moiety are generally slower but give better yields.The diastereoselectivity of the present "flash" dihydroxylation, anti to the existing α-stereogenic center, with cycloalkenes is excellent whereas that with acyclic alkenes is moderate to poor.Sodium metaperiodate is still the best co-oxidant for the catalytic reaction.Aqueous acetonitrile (approximately 86percent) as an alternative solvent system was found to give better yields of 1,2-diols than the original solvent system in some cases. - Keywords: alkenes, catalysis, dihydroxylations, electrophilicity, ruthenium compounds.

Enantiospezifische Synthesen von Valiolamin und dessen (1R)-, (2R)-, (1R,2R)-Diastereomeren aus (-)-Chinasaeure

Stichworte: Aminozucker, Asymmetrische Synthesen, Chinasaeure, Dihydroxylierungen, Valilamin