2'-O-Methylguanosine

Base Information

• Chemical Name: 2'-O-Methylguanosine
• CAS No.: 2140-71-8
• Molecular Formula: C11H15N5O5
• Molecular Weight: 297.27
• Hs Code.: 29349990
• Mol file: 2140-71-8.mol

Synonyms:2'-OMe-G;

Chemical Property of 2'-O-Methylguanosine

Chemical Property:

• Appearance/Colour: White solid
• Melting Point: 227-231°C (dec.)
• Boiling Point: 711.724 °C at 760 mmHg
• PKA: 9?+-.0.20(Predicted)
• Flash Point: 384.237 °C
• PSA: 148.51000
• Density: 1.983 g/cm³
• LogP: -1.45140
• Storage Temp.: Refrigerator
• Solubility.: Aqueous Base (Slightly), DMSO (Slightly),

Purity/Quality:

98% ^*data from raw suppliers

2''-O-MethylGuanosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-22
• Safety Statements: 26-36-60-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Description: 2''-O-Methylguanosine is a modified nucleoside that is produced in tRNAs by the action of tRNA guanosine-2’-O-methyltransferase, using S-adenosyl-L-methionine (Item Nos. 16376 | 13956) as a substrate. Through its interaction with other modified nucleosides, 2''-O-methylguanosine is thought to stabilize the structure of the tRNA. 2''-O-Methylguanosine can also be found in rRNA. Normal and modified nucleosides, including 2''-O-methylguanosine, have been shown to be secreted by a natural suppressor cell line and induce apoptosis in K562/Molt4 target cells.
• Uses: Guanosine analog. Guanosine analog. Used for preparation of nucleoside derivatives as inhibitors of RNA-dependent RNA viral polymerase.

Technology Process of 2'-O-Methylguanosine

There total 25 articles about 2'-O-Methylguanosine 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: 92.0%

2-amino-2'-O-methyladenosine (80791-87-3) → 2'-O-methylguanosine (2140-71-8)

Guidance literature:

With calf spleen adenosine deaminase; sodium phosphate; In dimethyl sulfoxide; at 20 ℃; for 36h; pH=7.4;

DOI:10.1080/15257770500544529

Reference yield: 91.0%

2-Amino-9-((2R,3R,3aR,9aR)-5,5,7,7-tetraisopropyl-3-methoxy-hexahydro-1,4,8-trioxa-5,7-disila-cyclopentacycloocten-2-yl)-1,9-dihydro-purin-6-one (572912-50-6) → 2'-O-methylguanosine (2140-71-8)

Guidance literature:

With triethylamine tris(hydrogen fluoride); In tetrahydrofuran; at 35 ℃; for 14h;

DOI:10.1016/S0960-894X(03)00291-9 DOI:10.1081/NCN-120021959

Reference yield: 90.0%

N1-benzyl-2'-O-methyl guanosine (194034-67-8) → 2'-O-methylguanosine (2140-71-8)

Guidance literature:

With naphthalene; sodium; In tetrahydrofuran;

DOI:10.1016/S0040-4020(00)00002-8

upstream raw materials:

2-amino-2'-O-methyladenosine

trimethylsulphonium hydroxide

G

6-(tert-Butyl-diphenyl-silanyloxy)-9-((2R,3R,3aR,9aR)-5,5,7,7-tetraisopropyl-3-methoxy-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-9H-purin-2-ylamine

Downstream raw materials:

N²-(4-monomethoxytrityl)-2'-O-methylguanosine

Pent-4-enoic acid (9-{(2R,3R,4R,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-methoxy-tetrahydro-furan-2-yl}-6-oxo-6,9-dihydro-1H-purin-2-yl)-amide

N²-isobutyryl-2′-O-methylguanosine

N²,2’-O-dimethylguanosine

Refernces

• 1、 -. "PROCESS FOR THE SYNTHESIS OF 2'-O-SUBSTITUTED PURINES". Page/Page column 8. . Retrieved 2008/12/07.
• 2、 Chow, Suetying,Wen, Ke,Sanghvi, Yogesh S.,Theodorakis, Emmanuel A.. "Novel synthesis of 2′-O-methylguanosine". . p. 1631 - 1634. Retrieved 2007/10/03.