2',3'-O-Isopropylideneguanosine

Base Information

• Chemical Name: 2',3'-O-Isopropylideneguanosine
• CAS No.: 362-76-5
• Molecular Formula: C13H17N5O5
• Molecular Weight: 323.308
• Hs Code.: 29349990
• Mol file: 362-76-5.mol

Synonyms:Guanosine,2',3'-O-isopropylidene- (6CI,7CI,8CI);Furo[3,4-d]-1,3-dioxole, guanosinederiv.;2',3'-Isopropylideneguanosine;2',3'-O-Isopropylideneguanosine;Isopropylideneguanosine;

Chemical Property of 2',3'-O-Isopropylideneguanosine

Chemical Property:

• Appearance/Colour: White Crystalline Solid
• Melting Point: 296 °C
• Boiling Point: 647 °C at 760 mmHg
• PKA: 9?+-.0.20(Predicted)
• Flash Point: 345.1 °C
• PSA: 137.51000
• Density: 1.93g/cm³
• LogP: -0.30720
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO, 15% Ammonium Hydroxide, Hot 50% aq. Ethanol, Methanol, Warm Water

Purity/Quality:

2',3'-O-Isopropylideneguanosine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: A useful precursor for the preparation of nucleic acids. 2',3'-O-Isopropylideneguanosine is a useful precursor for the preparation of nucleic acids

Technology Process of 2',3'-O-Isopropylideneguanosine

There total 12 articles about 2',3'-O-Isopropylideneguanosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

G (118-00-3) + 2,2-dimethoxy-propane (77-76-9) + acetone (67-64-1) → 2',3'-isopropylideneguanosine (362-76-5)

Guidance literature:

With toluene-4-sulfonic acid; at 20 ℃; for 72h; Inert atmosphere;

DOI:10.1021/acs.jnatprod.9b01231

Reference yield: 98.0%

G (118-00-3) + acetone (67-64-1) → 2',3'-isopropylideneguanosine (362-76-5)

Guidance literature:

With perchloric acid; at 20 ℃; for 1.16667h;

DOI:10.1039/c8ra05083j

Reference yield: 94.0%

G (118-00-3) + 2,2-dimethoxy-propane (77-76-9) → 2',3'-isopropylideneguanosine (362-76-5)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; at 25 ℃;

DOI:10.1016/j.tet.2009.08.057

upstream raw materials:

G

2,2-dimethoxy-propane

2-(Ethoxymethyl-amino)-9-((3aR,4R,6R,6aR)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-1,9-dihydro-purin-6-one

acetone

Downstream raw materials:

O^2',O^3'-isopropylidene-[5']guanylic acid bis-(4-nitro-phenyl ester)

O^{2'_,O3'_{-isopropylidene-O}5'}-trityl-guanosine

Guanosine 5'-monophosphate

guanosine-5'-diphosphate

Refernces

• 1、 Zhang,Cui,Sun. "Synthesis of 5'-deoxy-5'-thioguanosine-5'-monophosphorothioate and its incorporation into RNA 5'-termini.". . p. 275 - 278. Retrieved 2001.
• 2、 Devine, Shane M.,May, Lauren T.,Scammells, Peter J.. "Design, synthesis and evaluation of N6-substituted 2-aminoadenosine-5′-N-methylcarboxamides as A3 adenosine receptor agonists". . p. 192 - 196. Retrieved 2014.
• 3、 Shi,Fettinger,Davis. "Homochiral G-quadruplexes with Ba2+ but not with K+: The cation programs enantiomeric self-recognition [2]". . p. 6738 - 6739. Retrieved 2001.
• 4、 Warminski, Marcin,Kowalska, Joanna,Buck, Janina,Zuberek, Joanna,Lukaszewicz, Maciej,Nicola, Corina,Kuhn, Andreas N.,Sahin, Ugur,Darzynkiewicz, Edward,Jemielity, Jacek. "The synthesis of isopropylidene mRNA cap analogs modified with phosphorothioate moiety and their evaluation as promoters of mRNA translation". . p. 3753 - 3758. Retrieved 2013.
• 5、 Gonzalez-Rodriguez, David,Janssen, Pim G. A.,Martin-Rapn, Rafael,Cat, Inge De,Feyter, Steven De,Schenning, Albertus P. H. J.,Meijer. "Persistent, well-defined, monodisperse, π-conjugated organic nanoparticles via G-quadruplex self-assembly". . p. 4710 - 4719. Retrieved 2010.
• 6、 Way, Amanda E.,Korpusik, Angie B.,Dorsey, Taylor B.,Buerkle, Lauren E.,Von Recum, Horst A.,Rowan, Stuart J.. "Enhancing the mechanical properties of guanosine-based supramolecular hydrogels with guanosine-containing polymers". . p. 1810 - 1818. Retrieved 2014.
• 7、 Kumar, Y. Pavan,Bhowmik, Sudipta,Das, Rabindra Nath,Bessi, Irene,Paladhi, Sushovan,Ghosh, Rita,Schwalbe, Harald,Dash, Jyotirmayee. "A fluorescent guanosine dinucleoside as a selective switch-on sensor for c-myc G-quadruplex DNA with potent anticancer activities". . p. 11502 - 11506. Retrieved 2013.
• 8、 -. "Compositions and Methods for Reverse Automated Nucleic Acid Synthesis". Paragraph 0117-0118. . Retrieved 2019/10/29.
• 9、 Walczak, Sylwia,Sikorski, Pawel J.,Kasprzyk, Renata,Kowalska, Joanna,Jemielity, Jacek. "Exploring the potential of phosphotriazole 5′ mRNA cap analogues as efficient translation initiators". supporting information. p. 6741 - 6748. Retrieved 2018/09/29.