88270-97-7

Usage

Chemical structure

A derivative of D-ribose, a sugar molecule found in RNA, with multiple acetyl and benzoyl groups attached to it.

Acetyl groups

Two acetyl groups are attached to the sugar molecule, specifically at the 1st and 2nd positions (1,2-di-O-acetyl).

Benzoyl groups

Two benzoyl groups are attached to the sugar molecule, specifically at the 3rd and 6th positions (3,6-di-O-benzoyl).

Degree of acetylation

The compound has a high degree of acetylation due to the presence of two acetyl groups.

Degree of benzoylation

The compound has a high degree of benzoylation due to the presence of two benzoyl groups.

5-deoxy

Indicates that the sugar molecule has one less oxygen atom at the 5th position compared to a regular D-ribose molecule.

D-ribo-hexofuranose

The core sugar molecule is a D-ribose, which is a hexofuranose, meaning it has six carbon atoms and a furanose ring structure.

Chemical modification

The attachment of acetyl and benzoyl groups to the sugar molecule is a result of chemical modification, which can alter its properties and potential biological functions.

Research applications

Likely used in organic chemistry and biochemistry research to study the effects of chemical modifications on sugar molecules and their interactions with other molecules.

Context-dependent properties

The exact properties and applications of 1,2-di-O-acetyl-3,6-di-O-benzoyl-5-deoxy-D-ribo-hexofuranose may vary depending on the specific context in which it is being studied.

Upstream product

• 7022-86-8 1,2-O-isopropylidene-3,5,6-tri-O-p-tolylsulfonyl-α-D-allofuranose 
• 4056-10-4 1,2-O-Isopropyliden-6-O-triphenylmethyl-5-desoxy-α-D-xylo-hexofuran-5-enose 
• 124572-44-7 (5E)-3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-6-O-trityl-α-D-xylo-hexofuran-5-enose 
• 124572-48-1 6-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose 
• 124572-46-9 6-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose 
• 113808-25-6 3-O-benzoyloxy-5-deoxy-1,2-O-isopropylidene-α-D-ribohexofuranose 
• 124572-45-8 3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose 
• 124572-47-0 3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-6-O-trityl-α-D-xylo-hexofuranose 
• 113808-24-5 3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-6-O-trityl-α-D-ribo-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 
• 98-88-4 benzoyl chloride 
• 7057-09-2 1,2-O-isopropylidene-5-deoxy-α-D-glucofuranose 
• 613-90-1 benzoyl cyanide 

Downstream Products

• 124572-54-9 1-(2-O-acetyl-3,6-di-O-benzoyl-5-deoxy-β-D-ribo-hexofuranosyl)uracil 
• 88238-38-4 1-(5-deoxy-β-D-arabino-hexofuranosyl)cytosine 
• 55085-34-2 homocytidine 
• 22415-88-9 9-(5-Desoxy-β-D-ribo-hexofuranosyl)adenin 
• 55085-33-1 1-(O²-acetyl-O³,O⁶-dibenzoyl-β-D-ribo-5-deoxy-hexofuranosyl)-4-acetylamino-1H-pyrimidin-2-one 
• 124572-55-0 N⁶-benzoyl-9-(2-O-acetyl-3,6-di-O-benzoyl-5-deoxy-β-D-ribo-hexofuranosyl)adenine 

Relevant academic research and scientific papers

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.

SYNTHESES OF 1-(5-DEOXY-Β-D-arabino-HEXOFURANOSYL)CYTOSINE

1-(5-Deoxy-β-D-arabino-hexofuranosyl)cytosine (4'-homoara-C) (11), a higher homolog of the antileukemic agent ara-C(1-β-D-arabinofuranosylcytosine), was prepared by two independent routes.The first one involved the inversion of configuration at C-2' of the D-ribo epimer (1-(5-deoxy-β-D-ribo-hexofuranosyl)cytosine, 4'-homocytidine) by the diphenylcarbonate technique; the 5-deoxy-D-ribo-hexofuranosyl moiety of 4'-homocytidine was obtained by way of an anti-Markovnikov addition of iodine trifluoroacetate to the double bond of 5,6-dideoxy-1,2-O-isopropylidene-3-O-p-tolylsulfonyl-α-D-ribo-hex-5-enofuranose and reduction of the resulting iodide(s).In the second approach, 5-deoxy-1,2-O-isopropylidene-3-O-p-tolylsulfonyl-β-D-xylo-hexofuranose was acetolyzed and condensed with 4-acetyl-N-bis(trimethylsilyl)cytosine, and alkaline treatment gave 11 by way of a 2',3'-anhydro intermediate.The structure of 11, in particular the configuration at C-2', was confirmed by its 1H- and 13C-n.m.r. spectra.