88096-46-2

Upstream product

• 112996-05-1 2,4-dideoxy-3,6-di-O-benzyl-α- and β-D-threo-hexopyranoses 
• 112996-03-9 methyl 2,4-dideoxy-3,6-di-O-benzyl-α- and β-D-threo-hexopyranoside 
• 95641-15-9 1,6-anhydro-3-O-benzyl-2,4-dideoxy-β-D-threo-hexopyranoside 
• 50880-93-8 levoglucosan tritosylate 
• 14241-58-8 (1R,3S,5S)-6,8-dioxabicyclo[3.2.1]octan-3-ol 
• 82300-42-3 methyl 2,4-dideoxy-3-O-benzyl-α- and β-D-threo-hexopyranoside 

Downstream Products

• 116315-42-5 (2S,4S,10R)-1,4-dibenzyloxy-10-(dimethyl-t-butylsiloxy)-2-hydroxy-9,11-dimethyldodec-7-yn-6-one 
• 97848-40-3 (4S,6S)-4-Benzyloxy-6-benzyloxymethyl-2-[(3S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-hex-1-ynyl]-tetrahydro-pyran-2-ol 
• 105977-58-0 (4S,6S)-4-Benzyloxy-6-benzyloxymethyl-2-[(3S,4R)-3-methyl-4-(tetrahydro-pyran-2-yloxy)-hex-1-ynyl]-tetrahydro-pyran-2-ol 
• 116315-48-1 (2S,4S,9S,10R)-1,4-dibenzyloxy-2-hydroxy-9-methyl-10-tetrahydropyran-2-yloxydodec-7-yn-6-one 
• 112996-13-1 (4S,6S)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-2-<(3S,4R)-3-methyl-4-hydroxypent-1-ynyl>tetrahydrofuran 
• 116348-90-4 (2R,4S,6S)-4-benzyloxy-6-benzyloxymethyl-2-<(3S,4R)-4-dimethyl-t-butylsiloxy-3,5-dimethylhex-1-ynyl>-2-methoxytetrahydropyran 
• 116348-91-5 (2S,4S,6S)-4-benzyloxy-6-benzyloxymethyl-2-<(3S,4R)-4-dimethyl-t-butylsiloxy-3,5-dimethylhex-1-ynyl>-2-methoxytetrahydropyran 
• 116315-43-6 (2RS,4S,6S)-4-benzyloxy-6-benzyloxymethyl-2-<(3S,4R,5R)-4-dimethyl-t-butylsiloxy-3,5-dimethylhept-1-ynyl>-2-methoxytetrahydropyran 
• 116315-49-2 (4S,6S)-4-benzyloxy-6-benzyloxymethyl-2-<(3S,4R)-4-hydroxy-3-methylhex-1-ynyl>-2-methoxy-tetrahydropyran 

Relevant academic research and scientific papers

Preparation of a Chiral Lactone from Leavoglucosan; a Key Intermediate for Synthesis of the Spiroacetal Moietes of the Avermectins and Milbemycins

A synthesis of two diprotected (4S,6S)-4-hydroxy-6-hudroxymethyltetrahydropyran-2-ones has been developed from laevoglucosan.Reaction of these lactones with a substituted chiral lithium acetylide followed by hydrogenation and acid-catalysed cyclisation led to formation of the spiroacetal moiety of milbemycin α1 and α3.The acetylene was prepared by resolution of racemic material obtained from reaction of lithium acetylide and cis-butene epoxide.Alternatively a stereocontrolled synthesis was developed from (S)-methyl-3-hydroxy-2-methylpropionate which involved 'chelation controlled' addition of lithium dimethylcuprate to the corresponding tetrahydropyranyloxy aldehyde.