249757-80-0

Basic information

• Product Name: (2S)-[[2,7-dideoxy-6-C-methyl-3,4,6-tris-O-(phenylmethyl)-α-D-arabino-heptopyranosyl]oxy]propanoic acid ethyl ester
• Synonyms: (2S)-[[2,7-dideoxy-6-C-methyl-3,4,6-tris-O-(phenylmethyl)-α-D-arabino-heptopyranosyl]oxy]propanoic acid ethyl ester
• CAS NO: 249757-80-0
• Molecular Weight: 562.703
• Mol File: 249757-80-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S)-[[2,7-dideoxy-6-C-methyl-3,4,6-tris-O-(phenylmethyl)-α-D-arabino-heptopyranosyl]oxy]propanoic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-[[2,7-dideoxy-6-C-methyl-3,4,6-tris-O-(phenylmethyl)-α-D-arabino-heptopyranosyl]oxy]propanoic acid ethyl ester(249757-80-0)
• EPA Substance Registry System: (2S)-[[2,7-dideoxy-6-C-methyl-3,4,6-tris-O-(phenylmethyl)-α-D-arabino-heptopyranosyl]oxy]propanoic acid ethyl ester(249757-80-0)

Safety Data

• Hazardous Substances Data: 249757-80-0(Hazardous Substances Data)

Upstream product

• 687-47-8 (S)-Ethyl lactate 
• 249757-75-3 1,5-anhydro-2,7-dideoxy-6-C-methyl-3,4,6-tris-O-(phenylmethyl)-D-arabino-hept-1-enitol 

Downstream Products

• 1054640-35-5 (S)-2-[(2R,4R,5S,6S)-4,5-Bis-benzyloxy-6-(1-benzyloxy-1-methyl-ethyl)-tetrahydro-pyran-2-yloxy]-propionic acid 2-thioxo-2H-pyridin-1-yl ester 
• 249757-81-1 (2S)-2-[[2,7-dideoxy-6-C-methyl-3,4,6-tris-O-(phenylmethyl)-α-D-arabino-heptopyranosyl]oxy]propanoic acid 

Relevant articles and documents

Development of an effective chiral auxiliary for hydroxyalkyl radicals

The development of an effective chiral auxiliary for hydroxyalkyl radicals is delineated. Both the 2-tetrahydropyranyl (THP) and tri-O-benzyl-2-deoxy-α-D-glucopyranosyl (GLU) auxiliaries resulted in diastereoselective radical additions to methyl acrylate at -78°C (ds = 6/1 and 11/1, respectively). The developing stereochemistry at the radical center was completely under auxiliary control. Correlation experiments showed that the D-GLU auxiliary led to attack on the radical Si-face. The selectivity of these radical additions dropped-off considerably when the more reactive 2-nitropropene trap was employed. Computational studies suggested that the observed facial selectivity was due primarily to entropic factors in the transition state but that a smaller temperature-dependent enthalpic contribution was also involved. It was hypothesized that incorporation of a quaternary center at C-6 (THP numbering) would restore the facial selectivity with more reactive radical traps by restricting the orientations available to the incoming alkene. In the event, the trans-6-tert-butyltetrahydropyranyl (tBu-THP) auxiliary resulted in very good diastereoselection with 2-nitropropene (ds = 35/1 at -78°C, 15/1 at 0°C, and 8/1 at RT) as did the tri-O-benzyl-6,6-dimethyl-2-α-D-deoxyglucopyranosyl (diMe-GLU) auxiliary during additions to ethyl α-trifluoroacetoxyacrylate (ds = 10/1 at 0°C). A protocol for recovery of the sugar-derived chiral auxiliaries was also established. This work sets the stage for the development of a novel approach to 1, 3, 5...(2n + 1) polyols based on iterative radical homologation as well as the application of these pyranosidic auxiliaries to other synthetically important reactions.