130277-32-6

Basic information

• Product Name: 1,4-Anhydro-2-deoxy-3-O-[(tert-butyl)diphenylsilyl]-D-erythro-pent-1-enitol
• Synonyms: 1,4-Anhydro-2-deoxy-3-O-[(tert-butyl)diphenylsilyl]-D-erythro-pent-1-enitol;((2R,3S)-3-(tert-butyldiphenylsilyloxy)-2,3-dihydrofuran-2-yl)Methanol
• CAS NO: 130277-32-6
• Molecular Formula: C₂₁H₂₆O₃Si
• Molecular Weight: 354.51484
• Mol File: 130277-32-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 429.9±45.0 °C(Predicted)
• Appearance: /
• Density: 1.11
• PKA: 14.24±0.10(Predicted)
• CAS DataBase Reference: 1,4-Anhydro-2-deoxy-3-O-[(tert-butyl)diphenylsilyl]-D-erythro-pent-1-enitol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Anhydro-2-deoxy-3-O-[(tert-butyl)diphenylsilyl]-D-erythro-pent-1-enitol(130277-32-6)
• EPA Substance Registry System: 1,4-Anhydro-2-deoxy-3-O-[(tert-butyl)diphenylsilyl]-D-erythro-pent-1-enitol(130277-32-6)

Safety Data

• Hazardous Substances Data: 130277-32-6(Hazardous Substances Data)

Usage

Chemical structure

A complex organic compound derived from D-erythro-pent-1-enitol with a diphenylsilyl group attached to the 3-O position.

Functional groups

Contains a diphenylsilyl group, a tert-butyl group, and an enitol moiety.

Stereochemistry

The compound has an erythro configuration, which refers to the relative positioning of the functional groups on the chiral carbon atoms.

Reactivity

The tert-butyl and diphenylsilyl groups influence the reactivity and stability of the compound, making it useful in synthetic organic chemistry reactions.

Precursor

It serves as a precursor to other compounds, allowing for the synthesis of more complex organic molecules.

Applications

Potential applications in the field of organic chemistry, particularly in the synthesis of complex organic molecules.

Importance

Its unique structure and properties make it a valuable compound for research and development in organic chemistry.

Synthesis

The compound can be synthesized through various chemical reactions, utilizing its functional groups and reactivity.

Solubility

The compound's solubility properties may vary depending on the solvent used, but it is generally soluble in organic solvents.

Upstream product

• 105930-84-5 tert-butyl(((2R,3S)-3-((tert-butyldiphenylsilyl)oxy)-2,3-dihydrofuran-2-yl)methoxy)diphenylsilane 
• 83467-48-5 1-[(2R,4S,5R)-4-(tert-butyldiphenylsilanyloxy)-5-hydroxymethyltetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 130948-46-8 (2R,3S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-3-(tert-butyl-diphenyl-silanyloxy)-2,3-dihydro-furan 
• 40615-39-2 5'-O-(4-4'-dimethoxytrityl)thymidine 
• 50-89-5 thymidine 
• 289681-49-8 1-[(2R,4S,5R)-5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-{[(1,1-dimethylethyl)diphenylsilyl]oxy}tetrahydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione 
• 96760-92-8 1,4-anhydro-2-deoxy-5-O-[(1,1-dimethylethyl)dimethylsilyl]-D-erythro-pent-1-enitol 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 197719-60-1 3'-TBDPS-5'-p-Tol-thymidine 
• 35898-26-1 O^5'-(4-methyl-benzoyl)-thymidine 
• 175020-66-3 2-deoxy-3,5-di-O-(tert-butyldiphenylsilyl)-D-ribonolactone 
• 1228923-57-6 3-TBDPS-5-TMS-glycal 

Downstream Products

• 142189-92-2 1-(tetrahydropyran-2-yl)-7-<(tetrahydropyran-2-yl)oxy>pyrazolo<4,3-d>pyrimidine 
• 142189-91-1 (2'R)-cis-3-<2',5'-dihydro-4'-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-5'-(hydroxymethyl)-2'-furanyl>-1-(tetrahydropyran-2-yl)-7-<(tetrahydropyran-2-yl)oxy>pyrazolo<4,3-d>pyrimidine 
• 142189-93-3 1,1'-bis(tetrahydropyran-2-yl)-7,7'-bis<(tetrahydropyran-2-yl)oxy>3,3'-bispyrimidine> 
• 1027202-34-1 5-[(2R,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxymethyl-2,5-dihydro-furan-2-yl]-1H-pyrimidine-2,4-dione 
• 166266-21-3 2-Benzyloxy-5-<3'-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-β-D-glycero-pentofuran-3'-ulos-1'-yl>-3-methylpyridine 
• 166266-24-6 2-(Benzoylamino)-5-<(2'R)-cis-3'-2',5'-dihydro-4'-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-5'-(hydroxymethyl)-2'-furanyl>pyridine 
• 190263-32-2 4-Bromo-5-((2R,5R)-5-hydroxymethyl-4-oxo-tetrahydro-furan-2-yl)-2-(tetrahydro-pyran-2-yl)-2H-pyrazole-3-carboxylic acid methyl ester 
• 190263-27-5 5-[(2R,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxymethyl-2,5-dihydro-furan-2-yl]-2-(tetrahydro-pyran-2-yl)-2H-pyrazole-3,4-dicarboxylic acid diethyl ester 
• 289681-50-1 ((2R,5R)-3-(tert-Butyl-diphenyl-silanyloxy)-5-{5-methyl-6-[2-(4-nitro-phenyl)-ethoxy]-pyridin-3-yl}-2,5-dihydro-furan-2-yl)-methanol 
• 270925-65-0 [(2R,5R)-5-(6-Amino-pyridin-3-yl)-3-(tert-butyl-diphenyl-silanyloxy)-2,5-dihydro-furan-2-yl]-methanol 
• 503321-53-7 (2'R)-cis-5-[2',5'-dihydro-4'-((tert-butyldiphenyl)silyl)oxy-2'-furanyl]-2-aminoquinazoline 
• 642460-97-7 6-amino-3-{3'-[(1,1-dimethylethyl)diphenylsilyloxy]-β-D-glycero-pentofuran-3'-ulos-1'-yl}-5-nitro-1H-pyridin-2-one 
• 383882-58-4 2-[2-(4-nitrophenyl)ethoxy]-5-(β-D-glycero-pentofuran-3'-ulos-1'-yl)-3-methylpyridine 
• 289681-52-3 2-[2-(4-nitrophenyl)ethoxy]-5-(1',2'-dideoxy-β-D-erythro-pentofuranosyl)-3-methylpyridine 

Relevant articles and documents

Synthesis of a Novel Coumarin C-Riboside as a Photophysical Probe of Oligonucleotide Dynamics

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Synthesis of a dA-dT base pair analogue and its effects on DNA-ligand binding

Two nucleoside derivatives containing the base analogues 3-deazaadenine and 3-methyl-2-pyridone have been prepared as analogues of dA and dT, respectively. After conversion into the appropriately protected phosphoramidites, DNA sequences were prepared with site-specifically placed analogues. When present in a duplex DNA sequence, the analogues result in the deletion of one or both of the hydrogen bonding functional groups (the N3-nitrogen of dA and the O2-carbonyl of dT) present in the minor groove. Binding by two ligands, 4′,6-diamidine-2-phenyl indole (DAPI) and Hoechst 33258 in the minor groove has been probed using a variety of DNA sequences. These sequences contain a d(GAATTC)2 core with analogue nucleosides substituted for one or more of the dA and dT residues. DAPI bound strongly to any sequence that contained both O2-carbonyls of the central two dT residues. The presence of a dc3A residue did in some cases enhance binding. With one of the central O2-carbonyls deleted, the binding was noticeably reduced, and with both absent, no significant binding could be detected. Similar although less dramatic results were observed with Hoechst 33258 binding to analogue sequences.

Facile preparation of protected furanoid glycals from thymidine

The synthesis of O-silyl- and O-acyl-protected furanose glycals from free thymidine was investigated. The method of glycal formation reported by Pedersen et al. was successfully expanded to include 5-ester (toluoyl) protected glycals as well as various combinations of 5'-ester and 3- and 5- tert-butyldimethylsilyl and tert-butyldiphenylsilyl protection. Gram quantities of furanoid glycals can be prepared in a few days in two-four steps in overall yields ranging from 17 to 80%.