664966-24-9

Basic information

• Product Name: 3,6-Dioxabicyclo[3.2.0]heptane-7-methanol, 2-[(1R)-1,2-bis(phenylmethoxy)ethyl]-4-methoxy-1-(phenylmethoxy)-, (1R,2R,4R,5S,7R)-
• CAS NO: 664966-24-9
• Molecular Formula: C30H34O7
• Molecular Weight: 506.596
• Mol File: 664966-24-9.mol

Chemical Properties

• CAS DataBase Reference: 3,6-Dioxabicyclo[3.2.0]heptane-7-methanol, 2-[(1R)-1,2-bis(phenylmethoxy)ethyl]-4-methoxy-1-(phenylmethoxy)-, (1R,2R,4R,5S,7R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-Dioxabicyclo[3.2.0]heptane-7-methanol, 2-[(1R)-1,2-bis(phenylmethoxy)ethyl]-4-methoxy-1-(phenylmethoxy)-, (1R,2R,4R,5S,7R)-(664966-24-9)
• EPA Substance Registry System: 3,6-Dioxabicyclo[3.2.0]heptane-7-methanol, 2-[(1R)-1,2-bis(phenylmethoxy)ethyl]-4-methoxy-1-(phenylmethoxy)-, (1R,2R,4R,5S,7R)-(664966-24-9)

Safety Data

• Hazardous Substances Data: 664966-24-9(Hazardous Substances Data)

Upstream product

• 664966-21-6 methyl 2-O-methylsulfonyl-3,5,6-tri-O-benzyl-3-C-vinyl-β-D-allofuranoside 
• 664966-19-2 1,2-O-isopropylidene-3,5,6-tri-O-benzyl-3-C-vinyl-α-D-allofuranose 
• 151426-71-0 1,2-di-O-isopropylidene-3-C-vinyl-β-D-allofuranose 
• 100-39-0 benzyl bromide 
• 664966-23-8 methyl 2-O-methylsulfonyl-3-C-(1(R),2-dihydroxyethyl)-3,5,6-tri-O-benzyl-β-D-allofuranoside 
• 664966-20-5 methyl 3,5,6-tri-O-benzyl-3-C-vinyl-D-allofuranoside 

Downstream Products

• 664966-25-0 (1S,2R,4R,5S,7R)-1-benzyloxy-7-benzoyloxymethyl-2-(1(R),2-di(benzyloxy)ethyl)-4-methoxy-3,6-dioxabicyclo[3.2.0]heptane 

Relevant articles and documents

Synthesis of hydroxymethyl branched [3.2.0]bicyclic nucleosides using a regioselective oxetane ring-formation.

Two [3.2.0]bicyclic nucleosides, 35 and 34, with one and two hydroxymethyl substituents, respectively, have been efficiently synthesized. A protected (3'-C-vinyl-beta-D-allofuranosyl)thymine derivative 28 was easily prepared from diacetone-D-glucose and the thymine moiety was protected with a BOM-group. After the introduction of a leaving group in the 2'-position, the subsequent nucleoside 31 was used as the substrate for a stereoselective dihydroxylation and a regioselective oxetane ring-formation to give after deprotection the bicyclic nucleoside 34. The surprisingly efficient formation of an oxetane was first discovered by serendipity on a corresponding methylfuranoside derivative. The allo-configured bicyclic nucleoside 34 was easily shortened to a ribo-configured analogue 35 by a diol-cleaving reaction and subsequent reduction. Both 34 and 35 are conformationally restricted in the important intermediate 04'-endo conformation.