18439-34-4

Basic information

• Product Name: (3aR,5R,6S,6aR)-5-((S)-hydroxy(phenyl)methyl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole-6-ol
• Synonyms: (3aR,5R,6S,6aR)-5-((S)-hydroxy(phenyl)methyl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole-6-ol
• CAS NO: 18439-34-4
• Molecular Weight: 266.294
• Mol File: 18439-34-4.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: (3aR,5R,6S,6aR)-5-((S)-hydroxy(phenyl)methyl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole-6-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (3aR,5R,6S,6aR)-5-((S)-hydroxy(phenyl)methyl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole-6-ol(18439-34-4)
• EPA Substance Registry System: (3aR,5R,6S,6aR)-5-((S)-hydroxy(phenyl)methyl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole-6-ol(18439-34-4)

Safety Data

• Hazardous Substances Data: 18439-34-4(Hazardous Substances Data)

Upstream product

• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 18439-42-4 3-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-L-ido-pentofuranose 
• 65462-15-9 3-O-benzyl-1,2-O-isopropylidene-β-L-arabino-pentodialdo-1,4-furanose 
• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 
• 100-58-3 phenylmagnesium bromide 
• 70057-97-5 6-hydroxy-2,2-dimethyl-(3aR,5R,6S,6aR)-perhydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde 
• 108-86-1 bromobenzene 
• 152185-56-3 3-O-Allyl-1,2-O-isopropylidene-α-D-xylo-pentodialdose 
• 53167-11-6 1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 350255-13-9 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 1262487-77-3 (R)-((3aR,5S,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(phenyl)methyl cinnamate 
• 18439-35-5 (3aR,5R,6S,6aR)-5-((R)-hydroxy(phenyl)methyl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole-6-ol 
• 1262487-78-4 (R)-((3aR,5R,6S,6aR)-6-(cinnamoyloxy)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(phenyl)methyl cinnamate 
• 1233484-14-4 C₂₃H₂₂O₆ 
• 1233484-15-5 3-O-cinnamoyl-1,2-O-isopropylidene-5-C-phenyl-α-D-gluco-pentofuranose 
• 1233484-11-1 5-O-(tert-butyldiphenylsilyl)-3-O-cinnamoyl-1,2-O-isopropylidene-5-C-phenyl-α-D-gluco-pentofuranose 
• 1233484-17-7 5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-5-C-phenyl-α-D-gluco-pentofuranose 
• 1413282-40-2 3,5-O-carbonyl-1,2-O-isopropylidene-5-C-phenyl-β-L-idopentofuranose 
• 1190851-29-6 4-epi-(+)-crassalactone D 
• 1413282-41-3 C₁₂H₁₂O₆ 
• 1413282-45-7 7-epi-(+)-crassalactone D 
• 1413282-42-4 C₁₂H₁₂O₆ 
• 1241404-73-8 (5S,RP)-1,2-O-isopropylidene-5-phenyl-3,5-O-(5'-(2',3'-O-isopropiliden-5-metyluridinyl))phosphoryl-α-D-xylofuranose 

Relevant articles and documents

Conformational analysis of cyclic phosphates derived from 5-C′ substituted 1,2-O-isopropylidene-α-D-xylofuranose derivatives

Twelve 2-phenoxy-2-oxo-1,3,2-dioxaphosphorinanes fused with a 1,2-O-isopropylidene-α-D-xylofuranose moiety in cis orientation and substituted at the C′5 position were prepared in two steps from commercially available diacetone-α-D-glucose. Their conformations, and configurations were determined by 1H and 31P NMR and X-ray crystallographic techniques. Both, chair-twisted-chair and chair-boat equilibria were observed in solution. We observed that the strong anisotropic shielding effect of the benzene ring in the phenoxy group generates an upfield shift of the H1 hydrogen atom, when the cyclic phosphates adopt a boat conformation. This is due to a relative cis-orientation of the P-phenoxy group and the H1 proton of the 1,2-O-isopropylidene-α-D-xylofuranose moiety. Therefore, the configuration of the phosphorus center (SP or RP) can be determined by 1H NMR spectroscopy. Interestingly, the crystal structure of one of the cyclic phosphates exhibits two independent molecules in the asymmetric unit, one with a chair and the other one with a boat conformation.

Conformationally constrained goniofufurone mimics as inhibitors of tumour cells growth: Design, synthesis and SAR study

Synthesis of conformationally restricted (+)-goniofufurone (1) and 7-epi-(+)-goniofufurone (2) analogues, with embedded O-isopropylidene, O-methylidene or cyclic carbonate functions is disclosed starting from d-glucose. A number of potential bioisosteres

Divergent synthesis of cytotoxic styryl lactones isolated from Polyalthia crassa. The first total synthesis of crassalactone B

The first total synthesis of (+)-crassalactone B (2) and a new syntheses of (+)-crassalactone C (3) has been achieved starting from d-glucose. The natural products 2 and 3 can be selectively accessed by changing the conditions for TBDPS cleavage in the fi