124572-45-8

Basic information

• Product Name: 3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose
• Synonyms: 3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose
• CAS NO: 124572-45-8
• Molecular Weight: 308.331
• Mol File: 124572-45-8.mol

Chemical Properties

• CAS DataBase Reference: 3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose(124572-45-8)
• EPA Substance Registry System: 3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose(124572-45-8)

Safety Data

• Hazardous Substances Data: 124572-45-8(Hazardous Substances Data)

Upstream product

• 182412-45-9 Benzoic acid (3aR,5R,6S,6aR)-2,2-dimethyl-5-((R)-2-thioxo-[1,3]dioxolan-4-yl)-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 2816-87-7 1,2-di-O-isopropylidene-5,6-O-thiocarbonyl-α-D-glucofuranose 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 124572-44-7 (5E)-3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-6-O-trityl-α-D-xylo-hexofuran-5-enose 
• 4056-10-4 1,2-O-Isopropyliden-6-O-triphenylmethyl-5-desoxy-α-D-xylo-hexofuran-5-enose 
• 613-90-1 benzoyl cyanide 

Downstream Products

• 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 
• 113808-29-0 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 
• 113808-32-5 Benzoic acid (2R,3R,4R,5S)-4,5-diacetoxy-2-[2-(diethoxy-phosphoryl)-ethyl]-tetrahydro-furan-3-yl ester 
• 113808-27-8 1,2-di-O-acetyl-3-O-benzoyl-5,6-dideoxy-6-diethylphosphono-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 
• 113808-28-9 3-O-benzoyl-5,6-deoxy-6-diethylphosphono-1,2-O-isopropylidene-α-D-ribo-hexofuranose 
• 113808-26-7 3-O-benzoyl-6-bromo-5,6-dideoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose 
• 113808-25-6 3-O-benzoyloxy-5-deoxy-1,2-O-isopropylidene-α-D-ribohexofuranose 
• 124572-48-1 6-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose 
• 114071-55-5 N⁶-benzoyl-9-(2-O-acetyl-3-O-benzoyl-5,6-dideoxy-6-diethylphosphono-β-D-ribo-hexofuranosyl)adenine 
• 124572-51-6 1-(2'-O-acetyl-3'-O-benzoyl-5',6'-dideoxy-6'-phosphono-β-D-ribo-hexofuranosyl)uracil pyridinium salt 

Relevant articles and documents

Thio-sugars. I. Radical-promoted thione-thiol rearrangement of cyclic thionocarbonates: Synthesis of 5-thioglucose

The 5,6-O-thiocarbonyl-α-D-glucofuranose derivatives 2, when subjected to one of the following reactions, undergo a radical-promoted thione-thiol rearrangement to yield the 5-S-thiolcarbonates of gluco-configuration 8 as the major product. The reactions are, (A) thermolysis with a catalytic amount of tributyltin hydride and AIBN, (B) photolysis with hexabutyldistannane, and (C) thermolysis with dimethyl phosphonate and benzoyl peroxide. On the other hand, thermolysis of 2 with trialkylsilane (condition D) yielded olefins 13 as the major product. The 5-S-gluco product 8 was converted, in three steps, to 5-thioglucose (21) in 55% yield.

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.