115479-42-0

Basic information

• Product Name: 4-Methoxy-7--D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine
• Synonyms: 2-Amino-4-methoxy-7--D-ribofuranosylpyrrolo[2,3-d]pyrimidine;4-Methoxy-7--D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine
• CAS NO: 115479-42-0
• Molecular Formula: C12H16N4O5
• Molecular Weight: 296.28
• Product Categories: Chiral Reagents;Heterocycles
• Mol File: 115479-42-0.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Refractive Index: 1.775
• Solubility: Ethyl Acetate (sparingly), Methanol
• CAS DataBase Reference: 4-Methoxy-7--D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methoxy-7--D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine(115479-42-0)
• EPA Substance Registry System: 4-Methoxy-7--D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine(115479-42-0)

Safety Data

• Hazardous Substances Data: 115479-42-0(Hazardous Substances Data)

Usage

Chemical Properties

White Powder

Uses

4-Methoxy-7-β-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine (cas# 115479-42-0) is a compound useful in organic synthesis.

InChI:InChI=1/C12H16N4O5/c1-20-10-5-2-3-16(9(5)14-12(13)15-10)11-8(19)7(18)6(4-17)21-11/h2-3,6-8,11,17-19H,4H2,1H3,(H2,13,14,15)/t6-,7+,8+,11-/m1/s1

Upstream product

• 124-41-4 sodium methylate 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 149765-15-1 N-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl-propionamide 
• 480439-92-7 2-amino-5-iodo-3,7-dihydro-7-(β-D-ribofuranosyl)-4H-pyrrolo-[2,3-d]pyrimidin-4-one 
• 873792-73-5 2-amino-5-bromo-4-methoxy-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 115479-40-8 4-chloro-7-{5′-O-[(1,1-dimethylethyl)-dimethylsilyl]-2′,3′-O-(1-methylethylidene)-β-D-ribofuranosyl}-7H-pyrrolo[2,3-d]pyrimidine-2-amine 
• 115479-41-9 2-amino-4-methoxy-7-(2,3-O-isopropylidene-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine 
• 131981-22-1 7-{5'-O-[(1,1-dimethylethyl)dimethylsilyl]-2',3'-O-(1-methylethylidene)-β-D-ribofuranosyl}-4-methoxy-7H-pyrrolo[2,3-d]pyrimidin-2-amine 
• 120401-36-7 2-amino-4-chloro-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 84955-32-8 2-amino-4-methoxy-7H-pyrrolo[2,3-d]-pyrimidine 
• 84955-31-7 4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine 
• 102690-95-9 5-O-<(1,1-dimethylethyl)dimethylsilyl>-2,3-O-(1-methylethylidene)-β-D-ribofuranosyl chloride 

Downstream Products

• 62160-23-0 7-deazaguanosine 
• 62160-23-0 2-amino-7-β-D-ribofuranosylpyrrolo<2,3-d>pyrimidin-4(3H)-one 

Relevant articles and documents

Glycosylation of Pyrrolo[2,3- d]pyrimidines with 1- O-Acetyl-2,3,5-tri- O-benzoyl-β- d -ribofuranose: Substituents and Protecting Groups Effecting the Synthesis of 7-Deazapurine Ribonucleosides

Glycosylation of nonfunctionalized 6-chloro-7-deazapurine with commercially available 1-O-acetyl-2,3,5-tri-O-benzoyl-β-d-ribofuranose (45%) followed by amination and deprotection gave tubercidin in only two steps. Similar conditions applied for the synthe

A facile and improved synthesis of tubercidin and certain related pyrrolo[2,3-d]pyrimidine nucleosides by the stereospecific sodium salt glycosylation procedure [1]

A simple synthesis of tubercidin, 7-deazaguanosine and 2'-deoxy-7-deazaguanosine has been accomplished using the sodium salt glycosylation procedure. Reaction of the sodium salt of 4-chloro- and 2-amino-4-chloro-pyrrolo[2,3-d]pyrimidine, 3 and 4, respectively, with 1-chloro-2,3-O-isopropylidene,5-O-(t-butyl)dimethylsilyl-α-D-ribofur nose gave the corresponding protected nucleosides 6 and 7 with β-anomeric configuration. Deprotection of 6 provided 8, which on heating with methanolic ammonia gave tubercidin in excellent yield. Functional group transformation of 7, followed by deisopropylidenation gave 2-aminotubercidin and 2-amino-7-β-ribofuranosylpyrrolo[2,3-d]pyrimidine-4(3H)-thione. Treatment of 7 with 1N sodium methoxide followed by exposure to aqueous trifluoroacetic acid, and ether cleavage furnished 7-deazaguanosine. 2'-Deoxy-7-deazaguanosine and 2'-deoxy-7-deaza-6-thioguanosine were also prepared by using similar sequence of reactions employing 4 and 1-chloro-2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranose.