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

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

Uses

Used in Organic Synthesis:
4-(Hydroxymethyl)-1,2-O-isopropylidene-3-O-benzyl-beta-L-threo-pentofuranose is used as a key intermediate in the synthesis of nucleoside analogs and other bioactive molecules. Its functional groups allow for further chemical modifications, making it a valuable component in the development of pharmaceuticals and other bioactive compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-(Hydroxymethyl)-1,2-O-isopropylidene-3-O-benzyl-beta-L-threo-pentofuranose is used as a starting material for the synthesis of various therapeutic agents. Its unique structure and functional groups enable the design and development of novel drugs with potential applications in treating a wide range of diseases.
Used in Research and Development:
4-(Hydroxymethyl)-1,2-O-isopropylidene-3-O-benzyl-beta-L-threo-pentofuranose is also utilized in research and development for the exploration of new chemical reactions and the synthesis of innovative organic compounds. Its presence in various chemical libraries aids researchers in discovering new chemical entities with potential applications in various fields.

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

• 50-00-0 formaldehyd 
• 23558-05-6 3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose 
• 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 
• 100-39-0 benzyl bromide 
• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 
• 582-52-5 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 
• 350255-13-9 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 908142-25-6 1-2 O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose 

Downstream Products

• 258335-15-8 4-C-acetoxymethyl-5-O-acetyl-3-O-benzyl-1,2-O-(1-methylethylidene)-β-L-threo-pentofuranose 
• 230631-15-9 5-O-Benzoyl-4-C-benzoyloxymethyl-3-O-benzyl-1,2-O-isopropylidene-β-L-threo-pentofuranose 
• 410076-92-5 3-O-benzyl-5-O-(methanesulfonyl)-4-C-[[(methanesulfonyl)oxy]methyl]-1,2-O-isopropylidene-β-L-threo-pentofuranose 
• 72261-46-2 3-O-benzyl-5-(O-p-toluenesulfonyl)-4-C-(p-toluenesulfonyloxymethyl)-1,2-O-(isopropylidene)-β-L-threo-xylofuranose 
• 851050-35-6 3-O-benzyl-5-O-(tert-butyldimethylsilyl)-4-C-(tert-butyldimethylsilyloxymethyl)-1,2-O-isopropylidene-β-L-threo-pentofuranose 
• 897930-35-7 [6-benzyloxy-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-methanol 
• 897930-34-6 C₁₆H₂₀O₅ 
• 952716-08-4 (3aR,4aR,5R,6R)-[6-benzyloxy-5-(tert-butyldimethylsilanyloxymethyl)-2,2-dimethyltetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-methanol 
• 952716-09-5 (3aR,4aR,5R,6R)-5-allyloxymethyl-6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-ylmethoxy-tert-butyl-dimethyl-silane 
• 952716-10-8 (3aR,4aR,5R,6R)-(5-allyloxymethyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-methanol 
• 952716-11-9 (2'S,3'R,3'aR,6'aR,4aR,6aS)-6-benzyl-3'-benzyloxy-6-aza-3,5-dioxabicyclo[4.2.1]nonane-spiro-[1.2]-1',4',6'-trioxo-bicyclo[3.3.0]octane 
• 952716-12-0 (2'S,3'R,4'R,5'R,4aS,5aR)-4'-acetoxy-3'-benzyloxy-6-benzyl-5'-(1H,3H-pyrimidyl-2,4-dion-1-yl)-6-aza-3,5-dioxa-bicyclo[4.2.1]nonanespiro[1.2']tetrahydro-furan 
• 894430-39-8 methyl 3-O-benzyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-α,β-L-threo-pentofuranoside 
• 894430-40-1 methyl 2-azido-3-O-benzyl-2-deoxy-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-α,β-L-erythro-pentofuranoside 

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.

Total synthesis of 6- o -benzoylzeylenol from diacetone glucose

A total synthesis of 6-O-benzoylzeylenol from diacetone glucose is described. The key steps were a crossed aldol-Cannizzaro reaction to create a quaternary carbon stereocenter, and cyclization through ring closure metathesis (RCM). Of the four stereogenic centers, two were derived from diacetone glucose, the quaternary stereocenter was created by means of the crossed aldol-Cannizzaro reaction, and the fourth stereogenic center was produced by a Sharpless asymmetric epoxidation. Finally, cyclization through RCM and deprotection by removal of a benzyl group with titanium(IV) chloride gave the target molecule. Georg Thieme Verlag Stuttgart New York.

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.

An easy access to spiroannulated glyco-oxetane, -thietane and -azetane rings: synthesis of spironucleosides

The key intermediate 11 derived from d-glucose and possessing bis-mesylmethyl (MsO·CH2-) functionality at C-4, was used to generate spirocycles 12, 13 and 15 via one-step procedures. The spirocompounds 12 and 13 were subsequently converted into

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.

Selective sulfonylation of 4-C-hydroxymethyl-β-L-threo-pento-1,4- furanose: Synthesis of bicyclic diazasugars

Hydroxymethylation of α-D-xylo-pentodialdose 6 using excess formaldehyde and sodium hydroxide in THF-water (one pot aldol and crossed Cannizzaro reactions) followed by hydrogenolysis of C3-O-benzyl group afforded triol 8. The regio-selective α- and β-sulf