2774-28-9

Basic information

• Product Name: 1-O,2-O:5-O,6-O-Diisopropylidene-3-deoxy-α-D-erythro-3-hexenofuranose
• Synonyms: 1-O,2-O:5-O,6-O-Bis(1-methylethylidene)-3-deoxy-α-D-erythro-3-hexenofuranose;1-O,2-O:5-O,6-O-Diisopropylidene-3-deoxy-α-D-erythro-3-hexenofuranose;1-O,2-O:5-O,6-O-Diisopropylidene-3-deoxy-α-D-erythro-hexa-3-enofuranose
• CAS NO: 2774-28-9
• Molecular Formula: C₁₂H₁₈O₅
• Molecular Weight: 242.26832
• Mol File: 2774-28-9.mol
• Article Data: 36

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform; Methanol
• CAS DataBase Reference: 1-O,2-O:5-O,6-O-Diisopropylidene-3-deoxy-α-D-erythro-3-hexenofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1-O,2-O:5-O,6-O-Diisopropylidene-3-deoxy-α-D-erythro-3-hexenofuranose(2774-28-9)
• EPA Substance Registry System: 1-O,2-O:5-O,6-O-Diisopropylidene-3-deoxy-α-D-erythro-3-hexenofuranose(2774-28-9)

Safety Data

• Hazardous Substances Data: 2774-28-9(Hazardous Substances Data)

Usage

Description

1-O,2-O:5-O,6-O-Diisopropylidene-3-deoxy-α-D-erythro-3-hexenofuranose is a complex organic compound that serves as an intermediate in the synthesis of various biologically significant molecules. It is characterized by its unique structure, which includes diisopropylidene groups and a 3-deoxy-α-D-erythro-3-hexenofuranose core.

Uses

1. Used in Pharmaceutical Applications:
1-O,2-O:5-O,6-O-Diisopropylidene-3-deoxy-α-D-erythro-3-hexenofuranose is used as an intermediate in the synthesis of 6R,7R,8aR-Glucosepane (G595300), a structurally complex protein posttranslational modification. Glucosepane is believed to be present in all living organisms and has been linked to the pathophysiology of diabetes and human aging, making it a target for therapeutic intervention.
2. Used in Research and Development:
In the field of research, 1-O,2-O:5-O,6-O-Diisopropylidene-3-deoxy-α-D-erythro-3-hexenofuranose is utilized for the development of novel compounds and drugs targeting glucosepane-related conditions. Its unique structure allows for the exploration of new therapeutic approaches and the potential creation of more effective treatments for diabetes and aging-related diseases.
3. Used in Chemical Synthesis:
1-O,2-O:5-O,6-O-Diisopropylidene-3-deoxy-α-D-erythro-3-hexenofuranose is also employed in chemical synthesis processes, where its specific functional groups and structural features can be exploited to produce a variety of other complex organic molecules with potential applications in various industries, including pharmaceuticals, materials science, and agrochemicals.

Upstream product

• 3253-75-6 1,2:5,6-di-O-isopropylidene-3-O-tosyl-α-D-glucofuranoside 
• 55951-93-4 1,2:5,6-di-O-isopropylidene-3-O-triflyl-α-D-glucofuranose 
• 10581-12-1 tetramethyl ammonium acetate 
• 116408-84-5 2,2,2-Trifluoro-1,1-diphenyl-ethanesulfonic acid (3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 80667-81-8 1,2:5,6-di-O-isopropylidene-3-O-(N-imidazole-1-sulfonyl)-α-D-glucofuranose 
• 55951-90-1 1,2:5,6-di-O-isopropylidene-3-O-trifluoromethanesulfonyl-α-D-allofuranose 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 10368-86-2 1,2:5,6-di-O-isopropylidene-α-D-galactofuranose 
• 2595-05-3 Diacetone D-glucose 
• 3067-62-7 1,2:5,6-Di-O-isopropyliden-3-O-trimethylsilyl-D-glucofuranose 
• 116384-37-3 C₂₆H₂₉F₃O₆S 
• 116384-38-4 2,2,2-Trifluoro-1,1-diphenyl-ethanesulfonic acid (3aR,5R,6S,6aR)-5-((R)-1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 1003-29-8 2-pyrrole aldehyde 

Downstream Products

• 2774-29-0 (3aR,5R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole 
• 33647-85-7 isolevoglucosenone 
• 65462-15-9 3-O-benzyl-1,2-O-isopropylidene-β-L-arabino-pentodialdo-1,4-furanose 
• 65434-49-3 3-O-benzyl-1,2-O-isopropylidene-α-D-galactofuranose 
• 65451-98-1 3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-D-galactofuranose 
• 599196-25-5 C₁₅⁽¹³⁾CH₂₀O₄ 
• 599196-27-7 C₁₅⁽¹³⁾CH₂₀O₅ 
• 599196-29-9 C₁₅⁽¹³⁾CH₂₀O₅ 
• 599196-31-3 C₁₅⁽¹³⁾CH₂₂O₆ 
• 599196-33-5 C₁₅⁽¹³⁾CH₂₂O₆ 
• 599196-04-0 (2S,3S,4R)-2,4,5-Tris-benzyloxy-3-hydroxy-pentanal 
• 599196-08-4 C₂₆⁽¹³⁾CH₃₀O₄ 
• 599196-06-2 (2S,3S,4R)-2,4,5-Tris-benzyloxy-3-(1-methoxy-1-methyl-ethoxy)-pentanal 
• 599196-10-8 C₂₈⁽¹³⁾CH₃₄O₅ 

Relevant articles and documents

Novel Carbocyclization of a D-Glucose-derived Alkene

Cyclopentadiene reacts with a D-glucose-derived hex-3-enose derivative to give norbornene derivatives attached at the 2,3-position of a 1,6-anhydrohexose skeleton; although the bicyclic enone isolevoglucosenone is a plausible intermediate in this reaction, the products actually appear to arise through initial cycloaddition to a rearranged acyclic sugar derivative with subsequent generation of the anhydro ring.

A Mechanistic Study of the Photoreactions of Deoxy Iodo Sugars

Quantum yields of 0.31, 3.7, and 1.1 have been determined for the photochemical disappearance in heptane of 6-deoxy-6-iodo-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (1), 3-deoxy-3-iodo-1,2:5,6-di-O-isopropylidene-α-D-allofuranose (2), and 3-deoxy-3-iodo-1,2:3,4-di-O-isopropylidene-α-D-glucofuranose (3), respectively.The major reaction for compounds 2 and 3 is epimerization at C-3, a reaction not observable for compound 1.Photochemical epimerization takes place in at least two ways.First, carbon-iodine bond homolysis followed by recombination of the radicalsproduced either regenerates the starting iodide or gives its C-3 epimer.Second, a chain reaction takes place in which the propagation step involves transfer of an iodine atom from the deoxy iodo sugar (2 or 3) to the carbon radical produced by carbon-iodine bond homolysis.In the presence of oxygen a new set of photoproducts is formed.These include enol esters, alcohols, and carbonyl compounds.

Formal synthesis of fostriecin by a carbohydrate-based approach

The formal synthesis of fostriecin starting from d-glucose, involves chelation-controlled addition, Wittig rearrangement, ring closing metathesis and iodomethylenation, as described.

Studies on the Total Synthesis of Antibiotic Macrolactin S: A Conventional Approach for the Synthesis of the C1-C9 and C10-C24 Fragments

The C1-C9 and C10-C24 segments of the 24-membered polyene macrolide macrolactin S were synthesized by routes involving an epoxide-ring-opening reaction, an Ohira-Bestmann alkyne formation, a chelation-controlled nucleophilic addition reaction, and a Still

One-pot stereoselective double intramolecular oxymercuration: Synthesis of four isomers of an unsymmetrical bis-tetrahydrofuran ring system

Stereoselective one-pot double intramolecular oxymercuration has been demonstrated to be the key reaction in the efficient preparation of the mono-hydroxylated bis-tetrahydrofuran ring system present in asimitrin and salzmanolin, two naturally occurring b