23537-43-1

Basic information

• Product Name: 1-O,2-O-Isopropylidene-3-O-benzyl-5,6-dideoxy-5,6-didehydro-α-D-glucofuranose
• Synonyms: 2,2-Dimethyl-5α-vinyl-6α-(benzyloxy)-3aα,5,6,6aα-tetrahydrofuro[2,3-d]-1,3-dioxole;3-O-Benzyl-5,6-dideoxy-1-O,2-O-isopropylidene-α-D-xylo-hexa-5-enofuranose;3-O-Benzyl-5,6-dideoxy-1-O,2-O-isopropylidene-α-D-ribo-5-hexenofuranose;(3aR,3aα,6aα)-2,2-Dimethyl-5α-ethenyl-6α-(benzyloxy)tetrahydrofuro[2,3-d]-1,3-dioxole;1-O,2-O-Isopropylidene-3-O-benzyl-5,6-didehydro-5,6-dideoxy-α-D-glucofuranose;1-O,2-O-Isopropylidene-3-O-benzyl-5,6-dideoxy-5,6-didehydro-α-D-glucofuranose;1-O,2-O-Isopropylidene-3-O-benzyl-5,6-dideoxy-α-D-xylo-hexa-5-enofuranose
• CAS NO: 23537-43-1
• Molecular Formula: C₁₆H₂₀O₄
• Molecular Weight: 276.3276
• Mol File: 23537-43-1.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-O,2-O-Isopropylidene-3-O-benzyl-5,6-dideoxy-5,6-didehydro-α-D-glucofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1-O,2-O-Isopropylidene-3-O-benzyl-5,6-dideoxy-5,6-didehydro-α-D-glucofuranose(23537-43-1)
• EPA Substance Registry System: 1-O,2-O-Isopropylidene-3-O-benzyl-5,6-dideoxy-5,6-didehydro-α-D-glucofuranose(23537-43-1)

Safety Data

• Hazardous Substances Data: 23537-43-1(Hazardous Substances Data)

Upstream product

• 22331-20-0 O³-benzyl-O¹,O²-isopropylidene-O⁵,O⁶-bis-methanesulfonyl-α-D-allofuranose 
• 63593-02-2 3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose 
• 70798-12-8 1,2-O-isopropylidene-3-O-benzyl-α-D-ribofuranoside 
• 70632-45-0 (R)-1-((3aR,5R,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethanol 
• 155585-32-3 3-O-benzyl-1,2-O-isopropylidene-5-O-methylsulfonyl-6-O-triphenylmethyl-α-D-allofuranose 
• 155585-33-4 Methanesulfonic acid (R)-1-((3aR,5S,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-ethyl ester 
• 155585-34-5 (3aR,6R,6aR)-6-benzyloxy-2,2-dimethyl-5-[(2S)-oxiran-2-yl]tetrahydrofuro[2,3-d][1,3]dioxole 
• 155585-24-3 3-O-benzyl-6-deoxy-1,2-isopropylidene-β-L-talofuranose 
• 57099-04-4 3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose 
• 155585-29-8 Trifluoro-methanesulfonic acid (S)-1-((3aR,5S,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester 
• 117238-29-6 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-5-O-methylsulfonyl-α-D-allofuranose 
• 155585-25-4 3-O-benzyl-6-deoxy-1,2-isopropylidene-5-O-methylsulfonyl-β-L-talofuranose 
• 120575-53-3 (3aR,6S,6aR)-6-Benzyloxy-5-eth-(E)-ylidene-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole 

Downstream Products

• 81686-59-1 methyl 2-O-benzyl-4-deoxy-α-D-erythro-pentopyranoside 
• 81686-58-0 methyl 2-O-benzyl-4-deoxy-β-D-erythro-pentopyranoside 
• 5585-14-8 3,4-diphenyl-furazan 2-oxide 
• 137035-67-7 (5R)-5-(3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-tetrafuranos-4-yl)-3-phenyl-2-isoxazoline 
• 137035-68-8 (5S)-5-(3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-tetrafuranos-4-yl)-3-phenyl-2-isoxazoline 
• 137035-69-9 (5R)-5-(3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-tetrafuranos-4-yl)-3-ethoxycarbonyl-2-isoxazoline 
• 137035-70-2 (5S)-5-(3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-tetrafuranos-4-yl)-3-ethoxycarbonyl-2-isoxazoline 
• 81686-55-7 3-O-benzyl-5-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose 

Relevant articles and documents

From Oxygen to Sulfur and Back: Difluoro -H-phosphinothioates as a Turning Point in the Preparation of Difluorinated Phosphinates: Application to the Synthesis of Modified Dinucleotides

A simple, two-step procedure to convert α,α-difluorinated H-phosphinic acids into the corresponding H-phosphinothioates is described. The usefulness of these species is demonstrated by their transformation into difluorinated phosphinothioyl radicals and their addition onto alkenes. Additionally, sequential treatment of H-phosphinothioates by a strong base and a primary alkyl iodide constitutes an alternate route to the formation of the C-P bond. Both methods efficiently deliver difluorinated phosphinothioates. Similar reactions carried out with the fully oxygenated counterparts clearly indicate the superiority of the sulfur-based species and emphasize the crucial role played by sulfur in the construction of the second C-P bond. Oxidation easily transforms the thereby obtained phosphinothioates into the corresponding phosphinates. The whole strategy is applied to the stereoselective preparation of dinucleotide analogues featuring either a difluorophosphinothioyl or a difluorophosphinyl unit linking the two furanosyl rings.

Fluorination Reactions at C-5 of 3-O-Benzyl-6-deoxy-1,2-isopropylidenehexofuranoses

Fluorination reactions of 2-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-gluco-, β-L-ido-, α-D-allo-, and β-L-talo-furanoses (1, 2, 3, and 4) were investigated.The reaction of 1 with diethylaminosulfur trifluoride (DAST) predominantly produced 2-O-benzyl-5,6-dideoxy-5-fluoro-1,2-O-isopropylidene-α-D-glucofuranose with the retention of the configuration at C-5.Both of the fluorides with retained and inverted configurations were obtained in the fluorination of 2 with DAST.In contrast, only the inversion of the configuration occurred when 3 and 4 were reacted with DAST.The reactions of the methanesulfonates of 3 and 4 with tetrabutylammonium fluoride (TBAF) and those of their trifluoromethanesulfonates with tris(dimethylamino)sulfonium difluorotrimethylsilicate (TASF) gave the 5-deoxy-5-fluoro derivatives with the inversion of each configuration and the 5,6-unsaturated derivative.However, the reactions of the sulfonates of 1 and 2 overwhelmingly produced the 4,5- and 5,6-eliminated derivatives.For the reaction in which the steric hindrance of the benzyloxyl group at C-3 and the electronic repulsion of ring oxygen to the SN2 displacement with fluoride anion are significant, such as the fluorination of 1 with DAST, the SNi mechanism is reasonable.

Chirale Cyclobutanone durch -Cycloaddition von Dichlorketen an Kohlenhydratenolether

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