113808-25-6

Upstream product

• 4056-10-4 1,2-O-Isopropyliden-6-O-triphenylmethyl-5-desoxy-α-D-xylo-hexofuran-5-enose 
• 7057-09-2 1,2-O-isopropylidene-5-deoxy-α-D-glucofuranose 
• 124572-47-0 3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-6-O-trityl-α-D-xylo-hexofuranose 
• 113808-23-4 5-deoxy-1,2-O-isopropylidene-6-O-triphenylmethyl-α-D-ribo-hexofuranose 
• 37070-23-8 5-deoxy-1,2-O-isopropylidene-6-O-triphenylmethyl-α-D-xylohexofuranose 
• 124572-45-8 3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose 
• 124572-44-7 (5E)-3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-6-O-trityl-α-D-xylo-hexofuran-5-enose 
• 250696-99-2 Benzoic acid (3aR,5R,6R,6aR)-5-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(imidazole-1-carbothioyloxy)-ethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 250696-85-6 Benzoic acid (3aR,5R,6R,6aR)-5-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 98-88-4 benzoyl chloride 
• 189165-95-5 6-O-(tert-butyldimethylsilyl)-5-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose 
• 2595-05-3 Diacetone D-glucose 
• 31795-14-9 3-O-Benzoyl-1,2-O-isopropyliden-5,6-di-O-methylsulfonyl-α-D-allofuranose 
• 31795-13-8 3-O-benzoyl-1,2-O-isopropylidene-α-D-allofuranose 

Downstream Products

• 113808-26-7 3-O-benzoyl-6-bromo-5,6-dideoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose 
• 250696-87-8 6-O-benzyl-3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-D-allofuranose 
• 266349-13-7 3-O-benzoyl-7,7-dibromo-5,6,7-trideoxy-1,2-O-isopropylidene-α-D-ribo-hept-6-enofuranose 
• 1354483-64-9 1,4-anhydro-2-O-benzoyl-5-deoxy-6-O-tosyl-D-ribo-hexofuranitol 
• 1354483-65-0 1,4-anhydro-3-O-benzoyl-5-deoxy-6-O-tosyl-D-ribo-hexofuranitol 
• 1354483-63-8 3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-6-O-tosyl-α-D-ribo-hexofuranose 
• 55085-29-5 3,6-di-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose 
• 1354483-59-2 1,4-anhydro-2,6-O-dibenzoyl-5-deoxy-D-ribo-hexofuranitol 
• 1354483-60-5 1,4-anhydro-3,6-O-dibenzoyl-5-deoxy-D-ribo-hexofuranitol 
• 1354483-67-2 6-S-acetyl-1,4-anhydro-3-O-benzoyl-5-deoxy-6-thio-D-ribo-hexofuranitol 
• 1354483-66-1 6-S-acetyl-1,4-anhydro-2-O-benzoyl-5-deoxy-6-thio-D-ribo-hexofuranitol 
• 114071-56-6 Benzoic acid (2R,3R,4R,5R)-4-acetoxy-5-(6-benzoylamino-purin-9-yl)-2-(2-phosphono-ethyl)-tetrahydro-furan-3-yl ester 
• 113808-29-0 1-(2-O-acetyl-3-O-benzoyl-5,6-dideoxy-6-diethylphosphono-β-D-ribo-hexofuranosyl)uracil 
• 113808-31-4 Benzoic acid (2R,3R,4R,5R)-4-acetoxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(2-phosphono-ethyl)-tetrahydro-furan-3-yl ester 

Relevant academic research and scientific papers

Synthesis and properties of RNA analogues having amides as interuridine linkages at selected positions

Oligoribonucleotide analogues having amide internucleoside linkages (AM1: 3′-CH2CONH-5′ and AM2: 3′-CH 2NHCO-5′) at selected positions have been synthesized and the thermal stability of duplexes formed by these analogues with complem

Doubly homologated dihalovinyl and acetylene analogues of adenosine: Synthesis, interaction with S-adenosyl-L-homocysteine hydrolase, and antiviral and cytostatic effects

Treatment of the 6-aldehyde derived by Moffatt oxidation of 3-O-benzoyl- 1,2-O-isopropylideneα-D-ribo-hexofuranose (2c) with the dibromo- or bromofluoromethylene Wittig reagents generated in situ with tetrabromomethane or tribromofluoromethane, triphenylphosphine, and zinc gave the dihalomethyleneheptofuranose analogues 3b and 3d, respectively. Acetolysis, coupling with adenine, and deprotection gave 9-(7,7-dibromo-5,6,7-trideoxy- β-D-ribo-hept-6-enofuranosyl)adenine (5a) or its bromofluoro analogue 5b. Treatment of 5a with excess butyllithium provided the acetylenic derivative 9-(5,6,7-trideoxy-β-D-ribo-hept-6-ynofuranosyl)adenine (6). The doubly homologated vinyl halides 5a and 5b and acetylenic 6 adenine nucleosides were designed as putative substrates of the 'hydrolytic activity' of S-adenosyl-L- homocysteine (AdoHcy) hydrolase. Incubation of AdoHcy hydrolase with 5a, 5b, and 6 resulted in time- and concentration-dependent inactivation of the enzyme (K(i): 8.5 ± 0.5, 17 ± 2, and 8.6 ± 0.5 μM, respectively), as well as partial reduction of enzyme-bound NAD+ to E-NADH. However, no products of the 'hydrolytic activity' were observed indicating these compounds are type I mechanism-based inhibitors. The compounds displayed minimal antiviral and cytostatic activity, except for 6, against vaccinia virus and vesicular stomatitis virus (IC50: 15 and 7 μM, respectively). These viruses typically fall within the activity spectrum of AdoHcy hydrolase inhibitors.

Homologues of isomeric dideoxynucleosides as potential antiviral agents: Synthesis of isodideoxy-nucleosides with a furanethanol sugar moiety

The synthesis of a homologues series of compounds related to (R, S)- isodideoxynucleosides has been completed by coupling a variety of natural purine and pyrimidine bases with a modified sugar intermediate. This sugar precursor was prepared regiospecifica

USE OF 5-DEOXY-ribo-HEXOFURANOSE DERIVATIVES FOR THE PREPARATION OF 5'-NUCLEOTIDE PHOSPHONATES AND HOMORIBONUCLEOSIDES

A convenient and general method is proposed for the synthesis of 5'-nucleotide phosphonate analogs starting from 5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose which can easily be produced in preparative quantities from D-glucose.Phosphonate IIIa was synthesized by means of the Arbuzov reaction between 3-O-benzoyl-6-bromo-5,6-dideoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose and triethyl phosphite.The consecutive acetolysis, condensation with uracil and N6-benzoyladenine bis-trimethylsilyl derivatives and deblocking possessed phosphonate analogs of 5'-nucleotides in good yields.The intermediate 5-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose derivatives were used for the preparation of homonucleosides.

A NEW SCHEME FOR THE SYNTHESIS OF 5'-NUCLEOTIDE PHOSPHONATE ANALOGS

A convenient and general method is proposed for the synthesis of 5'-nucleotide phosphonate analogs starting from 5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose (1).