133604-44-1

Basic information

• Product Name: (2S,3R)-3-Benzyloxy-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-propionaldehyde
• Synonyms: (2S,3R)-3-Benzyloxy-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-propionaldehyde
• CAS NO: 133604-44-1
• Molecular Weight: 278.348
• Mol File: 133604-44-1.mol

Chemical Properties

• CAS DataBase Reference: (2S,3R)-3-Benzyloxy-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-propionaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R)-3-Benzyloxy-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-propionaldehyde(133604-44-1)
• EPA Substance Registry System: (2S,3R)-3-Benzyloxy-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-propionaldehyde(133604-44-1)

Safety Data

• Hazardous Substances Data: 133604-44-1(Hazardous Substances Data)

Upstream product

• 121964-06-5 (2R,3S,4S)-3-O-Benzyl-1,2-O-isopropylidene-4-methylpentane-1,2,3,5-tetrol 
• 100572-69-8 (2R,3S,4S)-3-Bnzyloxy-1,2-O-isopropylidene-4-methyl-5-hexene-1,2-diol 
• 100758-79-0 (2R,3R,4R)-3-Benzyloxy-1,2-O-isopropylidene-4-methyl-5-hexene-1,2-diol 

Downstream Products

• 1078119-22-8 C₂₀H₂₉NO₅ 
• 1078118-70-3 C₂₀H₂₉NO₅ 
• 133695-26-8 (2R,3S,4S,5R,6R)-3-O-benzyl-1,2-O-isopropylidene-4-methyl-5-vinylnonadecane-1,2,3,6-tetrol 
• 133604-09-8 (2R,3S,4S,5S,6S)-3-O-benzyl-1,2-O-isopropylidene-4-methyl-5-vinylnonadecane-1,2,3,6-tetrol 
• 133695-39-3 (3R,4R)-3-[(1R,2R)-2-Benzyloxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methyl-ethyl]-heptadec-1-en-4-ol 
• 133604-09-8 (3S,4S)-3-[(1R,2R)-2-Benzyloxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methyl-ethyl]-heptadec-1-en-4-ol 
• 133604-13-4 (2R,3S,4S,5S,6R,7S)-3-O-benzyl-7-O-((tert-butyldimethyl)silyl)-1,2-O-isopropylidene-4-methyl-5-vinyloctane-1,2,3,6,7-pentol 
• 133604-16-7 (2R,3S,4S,5S,6R,7S)-3-O-benzyl-1,2:6,7-di-O-isopropylidene-4-methyl-5-vinyloctane-1,2,3,6,7-pentol 
• 133604-08-7 (2R,3S,4S,5R,6S)-3-O-benzyl-1,2-O-isopropylidene-4-methyl-6-phenyl-5-vinylhexane-1,2,3,6-tetrol 
• 133604-14-5 (2R,3S,4S,5S,6R,7S)-3-O-benzyl-1,2-O-isopropylidene-4-methyl-5-vinyloctane-1,2,3,6,7-pentol 
• 133604-43-0 (E)-(4S,5S)-5-Benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-pent-2-en-1-ol 
• 133604-19-0 (2R,3S,4S,5R,6R,7S)-3-O-benzyl-1,2:6,7-di-O-isopropylidene-4-methyl-5-O-((methylsulfonyl)methyl)octane-1,2,3,6,7-pentol 
• 133604-17-8 (2'R,2S,3S,4S,5R)-4-(benzyloxy)-2-((2',2-isopropylidenedioxy)propyl)-3-methyl-5,6-(isopropylidenedioxy)hexanal 
• 133604-18-9 (2R,3S,4S,5R,6R,7S)-3-O-benzyl-1,2:6,7-di-O-isopropylidene-5-(hydroxymethyl)-4-methyloctane-1,2,3,6,7-pentol 

Relevant articles and documents

Epoxyamide-based strategy for the synthesis of polypropionate-type frameworks

(Chemical Equation Presented) A new approach to the stereoselective synthesis of polypropionate-type frameworks is reported utilizing reactions of amide-stabilized sulfur ylides with chiral aldehydes. To establish a new strategy for macrolide fragment synthesis, the stereoselectivity of these reactions in the construction of epoxy amides was the most important aspect of this study. In this aspect, we found a strong influence of the protecting groups employed in the starting aldehydes upon the stereochemical outcome of their reactions with the sulfur ylide 1. Thus, numerous aldehydes showed remarkable stereofacial differentiation, providing a major diastereoisomer, in contrast to others that displayed a poor or no stereoselectivity. Despite the difficulties encountered for some cases with respect to their diastereomeric yields, we were able to prepare various stereotetrads and stereopentads, thus enhancing the synthetic value of this new methodology for the preparation of typical polypropionate frameworks found in many natural products, in particular the macrolide class of antibiotics.

Highly Felkin-Anh Selective Hiyama Additions of Chiral Allylic Bromides to Aldehydes. Application to the First Synthesis of Nephromopsinic Acid and Its Enantiomer

The chromium(II)-mediated addition ("Hiyama reaction") of the chiral allylic bromides 13, 15, 19, 22, 24, and 27 to achiral and chiral aldehydes proceeds with high Felkin-Anh selectivity with respect to the stereocenter at Cγ in the bromide (Table II). By