ChemicalBook CAS DataBase List 5-Methyl-2'-deoxycytidine

5-Methyl-2'-deoxycytidine synthesis

9synthesis methods

Product Name:5-Methyl-2'-deoxycytidine
CAS Number:838-07-3
Molecular formula:C10H15N3O4
Molecular Weight:241.24

50-89-5 Synthesis

50-89-5
609 suppliers
$9.00/1g

838-07-3
242 suppliers
$9.00/100mg

Yield:838-07-3 92%

Reaction Conditions:

Stage #1: thymidinewith 1,8-diazabicyclo[5.4.0]undec-7-ene;((3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) in N,N-dimethyl-formamide at 20; for 0.0166667 h;
Stage #2: with ammonium hydroxide in N,N-dimethyl-formamide at 20; for 2 h;Reagent/catalyst;Time;

Steps:

General procedure for the synthesis of ^5MedC and oxidized ^5MedC derivatives (1′-20′)

General procedure: To a solution of the nucleosides (2-20) in DMF ([substrate]=0.3M, except for 3 and 4, [3,4]=0.05M) were added PyAOP (1.6 eq) and DBU (1.6 eq). The reaction was stirred at 20°C for 1min. To the reaction solution was added N-nucleophiles (4 eq) (or 1a in THF, conc. NH₄OH (10 eq)). The reaction was stirred at 20°C for 5min-4h and monitored by TLC. Upon completion, the solution was concentrated in vacuo. Flash column chromatography on silica gel afforded ^5MedC and oxidized ^5MedC derivatives (1′-20′) in pure form.

References:

Zheng, Xiu-An;Huang, Hua-Shan;Kong, Rui;Chen, Wei-Jie;Gong, Shan-Shan;Sun, Qi [Tetrahedron,2018,vol. 74,# 49,p. 7095 - 7101]