171252-87-2

Upstream product

• 135735-90-9 (1R,2R,3S)-3-O-Benzyl-5-benzyloxymethyl-1,2-O-cyclohexylidene-cyclohex-4-en-1,2,3-triol 
• 108-24-7 acetic anhydride 
• 183268-55-5 (1R,2R,3S,4S,5S)-3-O-benzyl-5-((benzyloxy)methyl)-1,2-O-cyclohexylidenecyclohexane-1,2,3,4,5-pentol 

Downstream Products

• 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 
• 171339-43-8 (1R,2R,3R,4S,5S)-1-azido-2,4,5-triacetyl-3-O-benzyl-5-((benzyloxy)methyl)cyclohexane-2,3,4,5-tetrol 
• 171252-91-8 (1S,2S,3R,4S,5S)-1-azido-2,4,5-tri-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)cyclohexane-2,3,4,5-tetrol 
• 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 

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.

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

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