32860-54-1

Basic information

• Product Name: 5-methylaminomethyl-2-thiouridine
• Synonyms: 5-methylaminomethyl-2-thiouridine;Uridine,5-[(methylamino)methyl]-2-thio-
• CAS NO: 32860-54-1
• Molecular Formula: C₁₁H₁₇N₃O₅S
• Molecular Weight: 303.33
• Mol File: 32860-54-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.58g/cm³
• Refractive Index: 1.691
• CAS DataBase Reference: 5-methylaminomethyl-2-thiouridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-methylaminomethyl-2-thiouridine(32860-54-1)
• EPA Substance Registry System: 5-methylaminomethyl-2-thiouridine(32860-54-1)

Safety Data

• Hazardous Substances Data: 32860-54-1(Hazardous Substances Data)

Usage

Uses

5-?(Methylaminomethyl)?-?2-?thiouridine is a wobble nucleoside present in bacterial tRNAs specific for Lys and Glu.

InChI:InChI=1/C11H17N3O5S/c1-12-2-5-3-14(11(20)13-9(5)18)10-8(17)7(16)6(4-15)19-10/h3,6-8,10,12,15-17H,2,4H2,1H3,(H,13,18,20)/t6-,7-,8-,10-/m1/s1

Upstream product

• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 89128-97-2 C₃₄H₂₈F₃N₃O₉S 
• 75921-10-7 N-[1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-oxo-2-thioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylmethyl]-N-methyl-acetamide 
• 54424-13-4 O^2'_,O3'_,O5'-tribenzoyl-5-methylaminomethyl-2-thio-uridine 
• 54424-07-6 Ethyl 3-propionate 
• 75921-12-9 Methyl-trimethylsilanyl-(4-trimethylsilanyloxy-2-trimethylsilanylsulfanyl-pyrimidin-5-ylmethyl)-amine 
• 75921-11-8 5-methylaminomethyl-2-thiouracil trifluoroacetate 
• 54424-08-7 5-(N-Methylacetamidomethyl)-2-thiouracil 
• 54424-09-8 5-(N-methyl-tert-butoxycarbonylamidomethyl)-2-thiouracil 
• 54424-10-1 N-methyl-N-(4-trimethylsilanyloxy-2-trimethylsilanylsulfanyl-pyrimidin-5-ylmethyl)-acetamide 
• 54424-11-2 methyl-(4-trimethylsilanyloxy-2-trimethylsilanylsulfanyl-pyrimidin-5-ylmethyl)-carbamic acid tert-butyl ester 
• 54424-12-3 5-[(acetyl-methyl-amino)-methyl]-O^2',O^3',O^5'-tribenzoyl-5-methylaminomethyl-2-thio-uridine 
• 58479-71-3 5-hydroxymethyl-2',3'-O-isopropylidene-2-thiouridine 
• 74-89-5 methylamine 

Downstream Products

• 72667-55-1 5-methylaminomethyluridine 

Relevant articles and documents

Synthesis of various substituted 5-methyluridines (xm5U) and 2-thiouridines (xm5s2U) via nucleophilic substitution of 5-pivaloyloxymethyluridine/2-thiouridine

5-Pivaloyloxymethyluridine and its 2-thio analogue have been utilized as convenient substrates for the synthesis of various 5-methyluridines (xm5U) and 5-methyl-2-thiouridines (xm5s2U). The pivaloyloxy group (OPiv) located at the pseudobenzylic position was effectively substituted with a series of nucleophiles: ammonia, primary and secondary amines including secondary cyclic amines, tetrabutylammonium salts of amino acids, an alkoxide and a thiolate.

THE PROTECTED DERIVATES OF 5-METHYLAMINOMETHYL-2-THIOURIDINE AND 5-CARBOMETHOXYMETHYL-2-THIOURIDINE AS COMPONENTS FOR THE OLIGONUCLEOTIDE SYNTHESIS

The syntheses of protected derivates of 5-methylaminomethyl-2-thiouridine(mnm5s2U) 11, 12 and 5-carbomethoxymethyl-2-thiouridine(mcm5s2U) 13 as well as their unprotected 3'-phosphates 14, 15 have been described.