55085-29-5

Upstream product

• 582-51-4 1,2-O-isopropylidene-α-D-allofuranose 
• 113808-25-6 3-O-benzoyloxy-5-deoxy-1,2-O-isopropylidene-α-D-ribohexofuranose 
• 98-88-4 benzoyl chloride 
• 7057-09-2 1,2-O-isopropylidene-5-deoxy-α-D-glucofuranose 
• 4056-10-4 1,2-O-Isopropyliden-6-O-triphenylmethyl-5-desoxy-α-D-xylo-hexofuran-5-enose 
• 7022-86-8 1,2-O-isopropylidene-3,5,6-tri-O-p-tolylsulfonyl-α-D-allofuranose 
• 88238-34-0 5,6-dideoxy-1,2-O-isopropylidene-3-O-p-tolylsulfonyl-α-D-ribo-hex-5-enofuranose 
• 620630-82-2 1,2 5,6-O-di(isopropylidene)-α-D-allofuranose 
• 613-90-1 benzoyl cyanide 
• 124572-48-1 6-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose 
• 113808-24-5 3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-6-O-trityl-α-D-ribo-hexofuranose 
• 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 

Downstream Products

• 88270-97-7 1,2-di-O-acetyl-3,6-di-O-benzoyl-5-deoxy-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 
• 124572-55-0 N⁶-benzoyl-9-(2-O-acetyl-3,6-di-O-benzoyl-5-deoxy-β-D-ribo-hexofuranosyl)adenine 
• 124572-54-9 1-(2-O-acetyl-3,6-di-O-benzoyl-5-deoxy-β-D-ribo-hexofuranosyl)uracil 
• 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 
• 55085-34-2 homocytidine 
• 88238-38-4 1-(5-deoxy-β-D-arabino-hexofuranosyl)cytosine 

Relevant academic research and scientific papers

Modeling of the ribonucleotide reductases substrate reaction. Hydrogen atom abstraction by a thiyl free radical and detection of the ribosyl-based carbon radical by pulse radiolysis

The 1,4-anhydro-5-deoxy-6-thio-D-ribo-hexofuranitol (1) was prepared from 1,2-O-isopropylidene-α-D-glucose in 10 steps. In a key step treatment of the 1,2-O-isopropylidenehexofuranose derivative with BF3/Et 3SiH effected deacetonization and reductive deoxygenation at carbon 1. Pulse radiolysis experiments with 6-thiohexofuranitol 1 and its disulfide derivative demonstrated formation of the ribosyl-based carbon-centered radical upon generation of 6-thiyl radical in basic medium. The proposed [1,5]-hydrogen shift abstraction with generation of the C3 radical mimics the initial substrate reaction of RNRs. The reversible H-atom transfer has been quantified and was correlated with the computed rate constants for the internal H atom abstraction from C1, C2, C3 and C4 by the thiyl radical. The energy barrier for the H3 and H4 abstractions were calculated to be most favorable with the corresponding barriers of 11.1 and 11.2 kcal/mol, respectively.

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.