62396-80-9

Basic information

• Product Name: 2(3H)-Furanone, 5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]dihydro-, (S)-
• CAS NO: 62396-80-9
• Molecular Formula: C11H22O3Si
• Molecular Weight: 230.379
• Mol File: 62396-80-9.mol
• Article Data: 22

Chemical Properties

• CAS DataBase Reference: 2(3H)-Furanone, 5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]dihydro-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2(3H)-Furanone, 5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]dihydro-, (S)-(62396-80-9)
• EPA Substance Registry System: 2(3H)-Furanone, 5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]dihydro-, (S)-(62396-80-9)

Safety Data

• Hazardous Substances Data: 62396-80-9(Hazardous Substances Data)

Upstream product

• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 69739-34-0 t-butyldimethylsiyl triflate 

Downstream Products

• 107036-52-2 2',3'-dideoxy-β-D-5-azacytidine 
• 107036-62-4 5-fluoro-2',3'-dideoxycytidine 
• 127592-40-9 2',3'-dideoxy-β-D-5-chlorouridine 
• 15379-30-3 2',3'-dideoxy-α-D-5-fluorouridine 
• 1601460-54-1 (3R,5S)-3-(3-(benzyloxy)-5-bromo-2-methoxybenzyl)-5-(((tert-butyldimethylsilyl)oxy)methyl)dihydrofuran-2(3H)-one 
• 133329-85-8 (1R,2S,4R)-2-Methoxy-4-methyl-1-(4-methyl-furan-2-yl)-5-trityloxy-pentan-1-ol 
• 133329-85-8 (1S,2S,4R)-2-Methoxy-4-methyl-1-(4-methyl-furan-2-yl)-5-trityloxy-pentan-1-ol 
• 133329-90-5 (2S,3S,5S,6R)-2,5-Dimethoxy-6-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-3-methyl-tetrahydro-pyran 
• 133329-90-5 (2S,3R,5S,6R)-2,5-Dimethoxy-6-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-3-methyl-tetrahydro-pyran 
• 133329-87-0 (2R,6S)-6-Methoxy-2-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-5-methyl-6H-pyran-3-one 
• 133329-89-2 (2R,3S,6S)-3,6-Dimethoxy-2-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-5-methyl-3,6-dihydro-2H-pyran 
• 133329-88-1 (2S,3S,6S)-6-Methoxy-2-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-5-methyl-3,6-dihydro-2H-pyran-3-ol 
• 133329-86-9 (2R,6S)-6-Hydroxy-2-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-5-methyl-6H-pyran-3-one 
• 133329-84-7 (2S,4R)-2-Methoxy-4-methyl-5-trityloxy-pentanal 

Relevant articles and documents

A transition metal-catalyzed enyne metathesis for the preparation of pyrrolizidine alkaloid core: Application towards the total synthesis of stemaphylline

In this paper, we disclose an efficient route for the synthesis of pyrrolizidine alkaloid core and its application towards the total synthesis of stemaphylline. The key pyrrolizidine core was achieved with Ru-carbene catalyzed ring closing enyne metathesis (RCEM). The effect of different types and amounts of Ru-carbene catalysts, solvents and temperature were systematically studied. The advantage of this method includes the construction of pyrrolizidine alkaloid core in a single operation.

Method for highly selective synthesis of multi-chiral central tetrahydrofuran ring

The invention relates to the technical field of organic synthesis, in particular to a method for highly selective synthesis of a multi-chiral central tetrahydrofuran ring. The method has mild conditions, simple reaction steps, easy operation, high regioselectivity and high stereoselectivity. The method comprises the following steps: (a) using L-glutamic acid 1 as a starting material, and carryingout diazotization and ring-closing to obtain a lactone intermediate 2; (b) reducing the carboxyl group in the lactone intermediate 2 to obtain an intermediate 3; (c) protecting the hydroxyl group in the intermediate 3 by TBS to obtain an intermediate 4; (d) carrying out a substitution reaction of the intermediate 4 to obtain an intermediate 5; (e) reducing the intermediate 5 to obtain a precursorcompound of an intermediate 6; (f) carrying out a Wittig reaction of the precursor compound of the intermediate 6 to obtain the intermediate 6; (g) carrying out a Mitsunobu reaction of the intermediate 6 to obtain an intermediate 7; and (h) performing protective group removal and ring-closing on the intermediate 7 under the action of a base to obtain a target product 8.

Design and Synthesis of New Acid Cleavable Linkers for DNA Sequencing by Synthesis

A new kind of acid sensitive tetrahydrofuranyl (THF) linker was synthesized and then reacted with 5-(6)-carboxytetramethylrhodaminesuccinimidyl ester (5(6)-TAMRA, SE), followed by di(N-succinimidyl) carbonate (DSC) and modified 2′-deoxyuridine triphosphate (dUTP); the final product, as a reversible terminator for DNA sequencing by synthesis (DNA SBS), was given obtained and confirmed by 1H-NMR, 31P-NMR, and HRMS with purity of up to 99%. The synthesized dye-labeled terminator incorporated into DNA strand successfully, and the fluorophore was cleaved completely under acidic conditions. The preliminary results encourage us to explore more acid-sensitive linkers for DNA SBS to increase the cleavage efficiency under weakly acidic conditions.