101527-68-8

Basic information

• Product Name: 1-[(2R,6R)-6-(hydroxymethyl)-1,4-dioxan-2-yl]pyrimidine-2,4(1H,3H)-dione
• Synonyms: 1-((2R,6R)-6-(Hydroxymethyl)-1,4-dioxan-2-yl)uracil; 1-[(2R,6R)-6-(Hydroxymethyl)-1,4-dioxan-2-yl]uracil
• CAS NO: 101527-68-8
• Molecular Formula: C₉H₁₂N₂O₅
• Molecular Weight: 228.202
• Mol File: 101527-68-8.mol

Chemical Properties

• Density: 1.42g/cm³
• Refractive Index: 1.549
• CAS DataBase Reference: 1-[(2R,6R)-6-(hydroxymethyl)-1,4-dioxan-2-yl]pyrimidine-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[(2R,6R)-6-(hydroxymethyl)-1,4-dioxan-2-yl]pyrimidine-2,4(1H,3H)-dione(101527-68-8)
• EPA Substance Registry System: 1-[(2R,6R)-6-(hydroxymethyl)-1,4-dioxan-2-yl]pyrimidine-2,4(1H,3H)-dione(101527-68-8)

Safety Data

• Hazardous Substances Data: 101527-68-8(Hazardous Substances Data)

Usage

Chemical structure

A compound with a pyrimidine-2,4(1H,3H)-dione structure and a 1,4-dioxan-2-yl group.

Stereochemistry

The stereochemistry of the molecule is specified as (2R,6R).

Functional groups

Contains a hydroxymethyl group attached to the 6th position of the dioxane ring.

Potential applications

May have potential applications in the pharmaceutical industry due to its structural features and functional groups.

Research and development

Properties and potential uses could be further explored in research and development for various applications such as drug discovery and synthesis.

Upstream product

• 101527-67-7 1-(R)-<6-(R)-trityloxymethyl-1,4-dioxan-2-yl>uracil 
• 101527-55-3 2,2'-anhydro-3'-O-(methylsulfonyl)-5'-O-(triphenylmethyl)-2',3'-secouridine 
• 135216-43-2 2'-O-acetyl-3'-O-(methylsulfonyl)-5'-O-(triphenylmethyl)-2',3'-secouridine 
• 101527-65-5 3'-O-(methylsulfonyl)-5'-O-(triphenylmethyl)-2',3'-secouridine 
• 135216-37-4 2',3'-bis-O-(methylsulfonyl)-2',3'-secouridine 
• 101552-16-3 2',3'-di-O-mesyl-5'-O-trityl-2',3'-seco-uridine 
• 101527-47-3 1-(2-hydroxy-1-{[1-hydroxy-3-(triphenylmethoxy)propan-2-yl]oxy}ethyl)pyrimidine-2,4(1H,3H)-dione 
• 110238-03-4 3'-O-(methylsulfonyl)-2',3'-secouridine 

Downstream Products

• 141947-30-0 2',3'-anhydro-5'-O-(4-tolylsulfonyl)-2',3'-secouridine 
• 135270-47-2 2',3'-anhydro-5'-O-benzoyl-2',3'-secouridine 

Relevant articles and documents

Regioselective Transformations of 2',3'-Seconucleosides into Anhydro Structures and Chiral Crown Ethers

Intramolecular cyclisation of properly protected and activated derivatives of 2',3'-secouridine (= 1--ethyl>uracil; 1) provided access to the 2,2'-, 2,3'-, 2,5'-, 2',5'-, 3',5'-, and 2',3-anhydro-2',3'-secouridines 5, 16, 17, 26, 28 and 31, respectively (Schemes 1-3).Reaction of 2',5'-anhydro-3'-O-(methylsulfonyl)- (25) and 2',3'-anhydro-5'-O-(methylsulfonyl)-2',3'-secouridine (32) with CH2Cl2 in the presence of 1,8-diazabicycloundec-7-ene generated the N(3)-methylene-bridged bis-uridine structure 37 and 36, respectively (Scheme 3).Novel chiral 18-crown-6 ethers 40 and 44, containing a hydroxymethyl and a uracil-1-yl or adenin-9-yl as the pendant groups in a 1,3-cis relationship, were synthesized from 5'-O-(triphenylmethyl)-2',3'-secouridine (2) and 5'-O,N6-bis(triphenylmethyl)-2',3'-secoadenosine (41) on reaction with 3,6,9-trioxaundecane-1,11-diyl bis(4-toluenesulfonate) and detritylation of the thus obtained (triphenylmethoxy)methyl compound 39 and 43, respectively (Scheme 4).

From nucleosides, their acyclo- and anhydro-analogues to chiral complementary lariat ethers

Novel 2',5'-(5), 2',3'-(13), 3',5'-anhydro-2',3'-seco-uridine (9) and syn-18-hydroxymethyl-2-[uracil-1-yl(20) and 2-adenin-9-yl(21)]-18-crown-6-ether, have been efficiently prepared from the respective, properly protected and activated 2',3'-seco-nucleosi

NUCLEOSIDE ANALOGUES WITH A 1,4-DIOXANE, 1,4-OXATHIANE OR 1,4-OXAZINE RING STRUCTURE AS THE CARBOHYDRATE FRAGMENT

Pyrimidine and purine nucleoside analogues with a 1,4-dioxane, 1,4-oxathiane or 1,4-oxazine ring structure have been prepared from the corresponding dimesylated seconucleosides by treatment with either sodium hydroxide, sodium sulfide or primary alkylamines.

The Chemistry of 2',3'-Seconucleosides. 1. Synthesis and Chemical and Biological Properties of Derivatives of 2',3'- Secouridine

Aspects of the chemistry of 2',3'-secouridine (1-(R)-1,5-dihydroxy-4-hydroxymethyl-3-oxapent-2-yl)uracil) derivatives have been studied. 5'-O-Trityl-2',3'-secouridine (4) was obtained from 5'-O-trityluridine by oxidation with periodate followed by reducti