72261-44-0

Basic information

• Product Name: 4-(Hydroxymethyl)-1,2-O-isopropylidene-3-O-benzyl-beta-L-threo-pentofuranose
• Synonyms: 4-(Hydroxymethyl)-1,2-O-isopropylidene-3-O-benzyl-beta-L-threo-pentofuranose;4-(HydroxyMethyl)-1,2-O-isopropylidene-3-O-benzyl;((3aR,6R,6aR)-6-(Benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5,5-diyl)dimethanol;[(3aR,6R,6aR)-5-(hydroxymethyl)-2,2-dimethyl-6-phenylmethoxy-6,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-5-yl]methanol
• CAS NO: 72261-44-0
• Molecular Formula: C₁₆H₂₂O₆
• Molecular Weight: 310.344
• Mol File: 72261-44-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 70-71 ºC
• Boiling Point: 442.5 °C at 760 mmHg
• Flash Point: 221.4 °C
• Appearance: /
• Density: 1.29
• Vapor Pressure: 1.3E-08mmHg at 25°C
• Refractive Index: 1.575
• Storage Temp.: 2-8°C
• PKA: 13.95±0.10(Predicted)
• CAS DataBase Reference: 4-(Hydroxymethyl)-1,2-O-isopropylidene-3-O-benzyl-beta-L-threo-pentofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(Hydroxymethyl)-1,2-O-isopropylidene-3-O-benzyl-beta-L-threo-pentofuranose(72261-44-0)
• EPA Substance Registry System: 4-(Hydroxymethyl)-1,2-O-isopropylidene-3-O-benzyl-beta-L-threo-pentofuranose(72261-44-0)

Safety Data

• Hazardous Substances Data: 72261-44-0(Hazardous Substances Data)

Usage

General Description

4-(Hydroxymethyl)-1,2-O-isopropylidene-3-O-benzyl-beta-L-threo-pentofuranose is a chemical compound that is used in organic synthesis. It is a derivative of pentofuranose, a five-carbon sugar. 4-(Hydroxymethyl)-1,2-O-isopropylidene-3-O-benzyl-beta-L-threo-pentofuranose has a hydroxyl group, a benzyl group, and an isopropylidene group attached to the pentofuranose backbone. It is commonly used in the synthesis of nucleoside analogs and other bioactive molecules. The presence of functional groups in this compound makes it a versatile building block for the creation of complex organic molecules.

InChI:InChI=1/C16H22O6/c1-15(2)20-12-13(19-8-11-6-4-3-5-7-11)16(9-17,10-18)22-14(12)21-15/h3-7,12-14,17-18H,8-10H2,1-2H3/t12-,13-,14+/m1/s1

Upstream product

• 100-39-0 benzyl bromide 
• 908142-25-6 1-2 O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose 
• 350255-13-9 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 591727-19-4 1-2,5-6 di-O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 
• 22529-61-9 (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 
• 50-00-0 formaldehyd 
• 23558-05-6 3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose 

Downstream Products

• 72261-46-2 3-O-benzyl-5-(O-p-toluenesulfonyl)-4-C-(p-toluenesulfonyloxymethyl)-1,2-O-(isopropylidene)-β-L-threo-xylofuranose 
• 851050-45-8 3-O-benzyl-3-C-ethynyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose 
• 851050-49-2 (1S,3R,4R,7S)-7-benzyloxy-7-ethynyl-1-(hydroxy)methyl-3-(uracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane 
• 851050-75-4 3-O-benzyl-3-C-ethynyl-4-C-(methanesulfonyloxy)methyl-5-O-methanesulfonyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose 
• 851050-73-2 (1R,3R,4R,5S)-1-(benzoyloxy)methyl-3-(cytosin-1-yl)-5-ethynyl-4-hydroxy-2,6-dioxabicyclo[3.2.0]heptane 
• 851050-71-0 (1R,3R,4R,5S)-1-(benzoyloxy)methyl-5-ethynyl-4-hydroxy-3-(uracil-1-yl)-2,6-dioxabicyclo[3.2.0]heptane 
• 851050-46-9 1,2-di-O-acetyl-3-O-benzyl-3-C-ethynyl-4-C-(methanesulfonyloxy)methyl-5-O-methanesulfonyl-D-erythro-pentofuranose 
• 851050-48-1 (1R,3R,4R,7S)-7-benzyloxy-7-ethynyl-1-(methanesulfonyloxy)methyl-3-(uracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane 
• 851050-77-6 Benzoic acid (1R,3R,4R,7S)-7-benzyloxy-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-7-ethynyl-2,5-dioxa-bicyclo[2.2.1]hept-1-ylmethyl ester 
• 851050-47-0 1-[2-O-acetyl-3-O-benzyl-3-C-ethynyl-4-C-(methanesulfonyloxy)methyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl]uracil 
• 851050-74-3 5-O-(4,4'-dimethoxytrityl)-4-C-(4,4'-dimethoxytrityloxy)methyl-3-C-ethynyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose 
• 851050-44-7 3-O-benzyl-5-O-(4,4'-dimethoxytrityl)-4-C-(4,4'-dimethoxytrityloxy)methyl-3-C-ethynyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose 
• 1418031-57-8 C₂₅H₄₀O₆Si 
• 1418031-59-0 C₃₀H₄₈O₇Si 

Relevant articles and documents

MODIFIED NUCLEOSIDE PHOSPHORAMIDITES

The present disclosure relates to compounds and compositions containing 5'-phosphoramidite nucleoside monomers of formulae (I) and (II), and methods of making and use, wherein the substituents are as defined in the appended claims.

TRICYCLIC NUCLEIC ACID ANALOGS

The present disclosure provides tricyclic nucleosides and oligomeric compounds prepared therefrom. The tricyclic nucleosides each have a tricyclic ribosyl sugar moiety wherein a bridge between the 2' and 4' ribosyl ring carbon atoms further comprises a fused carbocyclic or heterocyclic ring. The tricyclic nucleosides are expected to be useful for enhancing properties of oligomeric compounds including for example binding affinity and nuclease resistance.

Synthesis and biological evaluation of branched and conformationally restricted analogs of the anticancer compounds 3′-C-ethynyluridine (EUrd) and 3′-C-ethynylcytidine (ECyd)

The synthesis of branched and conformationally restricted analogs of the anticancer nucleosides 3′-C-ethynyluridine (EUrd) and 3′-C- ethynylcytidine (ECyd) is presented. Molecular modeling and 1H NMR coupling constant analysis revealed that the furanose rings of all analogs except the LNA analog are conformationally biased towards South conformation, and are thus mimicking the structure of ECyd. All target nucleosides were devoid of anti-HIV or anticancer activity.