125569-35-9

Upstream product

• 135697-04-0 (((4-bromobut-2-yn-1-yl)oxy)methyl)benzene 
• 1290543-85-9 1-O-benzyl-2-deoxy-2-C-ethenylidene-D-erythro-pentitol 
• 1290543-78-0 1-O-benzyl-4,5-O-isopropylidene-D-erythro-2-pentulose 
• 1290543-74-6 1-O-benzyl-2-deoxy-2-C-ethenylidene-4,5-O-isopropylidene-D-erythro-pentitol 
• 125569-33-7 Acetic acid (R)-3-benzyloxy-1-(R)-1,4-dioxa-spiro[4.5]dec-2-yl-2-oxo-propyl ester 
• 125569-32-6 Acetic acid (R)-3-benzyloxy-2-[(E)-2,6-dimethyl-phenylimino]-1-1,4-dioxa-spiro[4.5]dec-2-yl-propyl ester 
• 3587-60-8 Benzyloxymethyl chloride 
• 125569-34-8 (R)-3-Benzyloxy-1-(R)-1,4-dioxa-spiro[4.5]dec-2-yl-1-hydroxy-propan-2-one 

Relevant academic research and scientific papers

Indium-mediated allenylation of aldehydes and its application in carbohydrate chemistry: Efficient synthesis of D -ribulose and 1-deoxy- D -ribulose

A two-step reaction sequence starting with the indium-mediated allenylation of aldehydes with 4-bromo-2-butyn-1-ols and subsequent ozonolysis of the resulting allenylic product was developed to generate a variety of dihydroxyacetone derivatives. The regioselectivity of the indium-promoted C-C bond-forming reaction can be manipulated through hydroxy protecting groups on 4-bromo-2-butyn-1-ol, yielding either allenes or alkynes as preferred products. Compared to established protocols, the necessary amount of indium for this type of allenylation can be decreased by a factor of two to four. The versatility of this strategy was demonstrated in thestereoselective and straightforward synthesis of D-ribulose and 1-deoxy-D-ribulose. Copyright