173327-56-5

Basic information

• Product Name: 1,4-ANHYDRO-2-DEOXY-3,5-BIS-O-(T-BUTYLDIMETHYLSILYL)-D-ERYTHRO-PENT-1-ENITOL
• Synonyms: 1,4-ANHYDRO-2-DEOXY-3,5-BIS-O-(T-BUTYLDIMETHYLSILYL)-D-ERYTHRO-PENT-1-ENITOL;1,4-ANHYDRO-2-DEOXY-3,5-BIS-O-(TERT-BUTYLDIMETHYLSILYL)-D-ERTHYRO-PENT-1-ENITOL;Anhydro-2-deoxy-3,5-bis-O-(t- butyldimethylsilyl)-D-erythro-pent-1-enitol;D-erythro-Pent-1-enitol, 1,4-anhydro-2-deoxy-3,5-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-;1,4-Anhydro-3,5-bis-O-(tert-butyldimethylsilyl)2-deoxy-D-erythro-pent-1-enitol
• CAS NO: 173327-56-5
• Molecular Formula: C₁₇H₃₆O₃Si₂
• Molecular Weight: 344.64
• Mol File: 173327-56-5.mol

Chemical Properties

• Boiling Point: 336.6±42.0 °C(Predicted)
• Appearance: /
• Density: 0.91±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 1,4-ANHYDRO-2-DEOXY-3,5-BIS-O-(T-BUTYLDIMETHYLSILYL)-D-ERYTHRO-PENT-1-ENITOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-ANHYDRO-2-DEOXY-3,5-BIS-O-(T-BUTYLDIMETHYLSILYL)-D-ERYTHRO-PENT-1-ENITOL(173327-56-5)
• EPA Substance Registry System: 1,4-ANHYDRO-2-DEOXY-3,5-BIS-O-(T-BUTYLDIMETHYLSILYL)-D-ERYTHRO-PENT-1-ENITOL(173327-56-5)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 173327-56-5(Hazardous Substances Data)

Usage

Molecular structure

A complex chemical compound with a unique arrangement of atoms and functional groups.

Derivative of D-erythro-pent-1-enitol

It is derived from the parent compound D-erythro-pent-1-enitol.

Modification

The hydroxyl groups at the 3rd and 5th positions are replaced with t-butyldimethylsilyl (TBS) groups.

Purpose of modification

The TBS groups protect the hydroxyl groups from unwanted reactions, allowing for selective manipulation of other parts of the molecule.

Common use in organic chemistry

The compound is frequently used in the synthesis of complex natural products and pharmaceuticals.

Role in chemical transformations

Its unique structure and reactivity play a crucial role in facilitating specific chemical transformations in the synthesis of complex molecules.

Synthesis applications

The compound is particularly useful in the synthesis of complex natural products and pharmaceuticals due to its protective and reactive properties.

Protection of functional groups

The TBS groups provide a way to temporarily protect the hydroxyl groups, allowing chemists to perform reactions on other parts of the molecule without interference.

Selective reactivity

The compound's structure allows for selective reactivity, which is essential for the synthesis of complex molecules with multiple functional groups.

Importance in pharmaceutical development

The compound's unique properties make it a valuable tool in the development of new pharmaceuticals, as it can facilitate the synthesis of complex drug molecules with specific biological activities.

Upstream product

• 90344-34-6 3,5-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-deoxy-D-ribose 
• 64911-18-8 3',5'-O-di(tert-butyldimethylsilyl)-2'-deoxyuridine 
• 675598-22-8 tert-butyl (((2R,3S)-3-((tert-butyldimethylsilyl)oxy)-5-methoxytetrahydrofuran-2-yl)methoxy)dimethylsilane 
• 51255-17-5 1-O-methyl-2-deoxy-D-ribofuranoside 
• 50-89-5 thymidine 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 34371-14-7 2-deoxy-D-ribonolactone 
• 452-51-7 D-2-deoxyribose 
• 83159-91-5 3,5-di-O-(tert-butyldimethylsilyl)-2-deoxy-D-ribono-1,4-lactone 
• 40733-26-4 3',5'-O-di(tert-butyldimethylsilyl)thymidine 

Downstream Products

• 307306-09-8 3-fluoro-4-(β-D-glycero-pentofuran-3-ulos-1-yl)aniline 
• 307306-11-2 5-fluoro-4-(β-D-glycero-pentofuran-3-ulos-1-yl)-2-methylaniline 
• 307306-10-1 2,5-difluoro-4-(β-D-glycero-pentofuran-3-ulos-1-yl)aniline 
• 1064073-93-3 (2R,5R)-2-((tert-butyldimethylsilyloxy)methyl)-5-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl)dihydrofuran-3(2H)-one 
• 174865-51-1 4-[(4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydro-furan-2-yl]-4-hydroxy-cyclohexa-2,5-dienone 
• 1445-07-4 pseudouridine 
• 39967-60-7 2'-Deoxypseudouridine 

Relevant articles and documents

SYNTHESIS OF FLUORINATED NUCLEOTIDES

The present invention relates to efficient processes useful in the preparation of fluorinated nucleosides, such as (O-{[(2R,3R,4S,5R)-5-(6-amino-9H-purin-9-yl)-4-fluoro-3-hydroxyoxolan-2-yl]methyl}O,O-dihydrogen phosphorothioate, also known as 2'-(S)-fluoro-thio-adenosine monophosphate or 2'-F-thio-AMP. Such fluorinated nucleosides may be useful as a biologically active compound and or as an intermediate for the synthesis of more complex biologically active compounds. The present invention also encompasses intermediates useful in the disclosed synthetic processes and the methods of their preparation.

Organocatalytic Conversion of Nucleosides to Furanoid Glycals

A class of organocatalysts that are highly active for the conversion of 2′-deoxynucleosides to furanoid glycals have been discovered. These phosphorimides, (Ph2PS)2NH and (Ph2PSe)2NH, were shown to effectively mediate persilylation of 2′-deoxynucleosides

Decatungstate-Mediated C(sp3)–H Heteroarylation via Radical-Polar Crossover in Batch and Flow

Photocatalytic hydrogen atom transfer is a very powerful strategy for the regioselective C(sp3)–H functionalization of organic molecules. Herein, we report on the unprecedented combination of decatungstate hydrogen atom transfer photocatalysis with the oxidative radical–polar crossover concept to access the direct net-oxidative C(sp3)–H heteroarylation. The present methodology demonstrates a high functional group tolerance (40 examples) and is scalable when using continuous-flow reactor technology. The developed protocol is also amenable to the late-stage functionalization of biologically relevant molecules such as stanozolol, (?)-ambroxide, podophyllotoxin, and dideoxyribose.

Genetic Code Expansion Facilitates Position-Selective Labeling of RNA for Biophysical Studies

Nature relies on reading and synthesizing the genetic code with high fidelity. Nucleic acid building blocks that are orthogonal to the canonical A-T and G-C base-pairs are therefore uniquely suitable to facilitate position-specific labeling of nucleic aci

Synthesis of Benzophenone Nucleosides and Their Photocatalytic Evaluation for [2+2] Cycloaddition in Aqueous Media

Four benzophenone nucleosides that are para-substituted (-NH2, -NMe2, -OMe, and -Me) in relation to the carbonyl group were synthesized and characterized by their optical properties. The electron-donating character of the substituent

A nucleobase analogue that pairs strongly with adenine

Shaping up for an A: Adenine is the only canonical nucleobase that does not offer a third hydrogen-bonding functionality at its Watson-Crick face, making it difficult to bind with high affinity. A 6-ethynyl-2-pyridone binds more tightly and with greater sequence fidelity than thymine. VdW=van der Waals interactions. Copyright

Modular and practical synthesis of 6-substituted pyridin-3-yl C-nucleosides

(Chemical Equation Presented) A novel modular and practical methodology for preparation of 6-substituted pyridin-3-yl C-nucleosides was developed. The Heck reaction of 2-chloro-5-iodopyridine with a 3′-TBDMS-protected glycal gave a 6-chloropyridin-3-yl nu

Syntheses of 4-[1-(2-deoxy-β-D-ribofuranosyl)]-derivatives of 2-substituted-5-fluoroaniline: 'Cytosine replacement' analogs of deoxycytidine for evaluation as anticancer and antihuman immunodeficiency virus (anti-HIV) agents

A group of 4-[1-(2-deoxy-β-D-ribofuranosyl)]-derivatives of 5-fluoroaniline possessing a variety of aryl C-2 substituents (6a R = H, 6b R = F, 6c R = Me) were synthesized. Accordingly, a Heck-type coupling reaction of the 4-iodoaniline derivatives (13a-c) with the bis(tert-butyldimethylsilyl)glycal (11) in the presence of Pd(OAc)2 and Ph3As, followed by removal of the tert-butyldimethylsilyl protection groups using n-Bu4N+F-, yielded the corresponding 4-(β-D-glycero-pentofuran-3-ulos-1-yl)aniline derivatives (14a-c) having a C-3 C=O in the sugar ring. Reduction of the C-3 C=O compounds (14a-c) using NaB(OAc)3H afforded the target 4-[1-(2-deoxy-β-D-ribofuranosyl)]-derivatives of the respective 2-substituted-5-fluoroaniline (6a-c). The deoxycytidine mimic, 3-fluoro-4-[1-(2-deoxy-β-D-ribofuranosyl)]aniline (6a), in which the cytosine ring of deoxycytidine is replaced by a 4-(3-fluoroaniline) ring system, was inactive as an anticancer agent against a variety of tumor cell lines, and as an antihuman immunodeficiency virus (HIV-1, HIV-2) agent. The failure of this unnatural deoxycytidine mimic (6a) to exhibit anticancer-antiviral activity may be due to its inability to undergo phosphorylation by host cell- and virus-induced kinases.

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%.