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

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

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

• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 55951-90-1 1,2:5,6-di-O-isopropylidene-3-O-trifluoromethanesulfonyl-α-D-allofuranose 
• 1003-29-8 2-pyrrole aldehyde 
• 80667-81-8 1,2:5,6-di-O-isopropylidene-3-O-(N-imidazole-1-sulfonyl)-α-D-glucofuranose 
• 109-97-7 pyrrole 
• 124-63-0 methanesulfonyl chloride 
• 329899-64-1 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 55951-93-4 3-trifluoromethanesulphonate-1,2:3,4-di-O-isopropylidene-α-D-glucofuranose 
• 350255-13-9 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 33842-02-3 dichloromethylenedimethyliminium chloride 
• 67337-61-5 3-deoxy-3-iodo-1,2:5,6-di-O-isopropylidene-α-D-allofuranose 
• 14260-27-6 3-deoxy-3-iodo-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 582-52-5 1,2:5,6-diacetone-D-glucose 
• 77-76-9 2,2-dimethoxy-propane 

Downstream Products

• 33647-85-7 isolevoglucosenone 
• 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 
• 4005-35-0 3-Desoxy-D-galaktose 
• 65434-50-6 3-O-benzyl-5,6-dideoxy-6-C-(n-hexyl)-1,2-O-isopropylidene-β-L-arabino-hex-5-enofuranose 
• 98855-09-5 3-O-benzyl-5-deoxy-5-C-(n-heptyl)-1,2-O-isopropylidene-β-L-arabinofuranose 
• 599196-20-0 C₃₆⁽¹³⁾CH₄₂O₁₀S 
• 599196-18-6 C₂₈⁽¹³⁾CH₃₆O₇ 

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.

Synthesis of novel N-carbohydrate-derived heterocyclic compounds by nucleophilic substitution reaction of carbohydrate imidazole-1-sulfonates

The nucleophilic substitution reaction of carbohydrate imidazole-1- sulfonates with pyrrole and other nitrogen heterocyclic compounds is reported for the first time. Several novel N-carbohydrate-derived heterocyclic compounds have been prepared by this displacement reaction. The desired carbon-nitrogen bond formation proceeds under mild conditions to generate the coupling products in good yields with readily available and inexpensive reagents. This method is particularly suitable for carbohydrate imidazole-1-sulfonates of primary alcohols. Supplemental materials are available for this article. Go to the publisher's online edition of Journal of Carbohydrate Chemistry to view the free supplemental file. Taylor & Francis Group, LLC.

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.

Cross dehydrogenative coupling of sugar enol ethers with terminal alkenes in the synthesis of pseudo-disaccharides, chiral oxadecalins and a conjugated triene

An efficient strategy for the synthesis of C-2 and C-3 branched sugar dienes via cross dehydrogenative coupling of sugar enol ethers with terminal alkenes was developed. Both pyran and furan based enol ethers coupled smoothly with electron rich as well as deficient alkene sources yielding sugar dienes with complete E-stereoselectivity. This coupling reaction was applied successfully for the synthesis of orthogonally protected pseudo-C-saccharides as an alternative to olefin metathesis. Substrate scope was further enhanced by reacting exoglycals with methyl acrylate to generate C-5 branched sugars with moderate diastereoselectivity. These diene subunits were reacted with maleic anhydride under [4 + 2] cycloaddition conditions to generate highly functionalised chiral oxadecalin cores. Finally, utilizing this C-C bond formation, a sugar based conjugated triene was synthesized in excellent yield and selectivity.

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.

Cycloaddition of cyclopentadiene to 3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose. Synthesis and representative chemistry of 1,6-anhydro-2,3-dideoxy-β-D-glycero-hex-2-enopyran-4-ulose ("isolevoglucosenone")

Treatment of D-glucose-derived alkene 4 with cyclopentadiene in the presence of a Lewis acid results in the formation of cycloaddition products 8-11. Evidence is presented to show that these 1,6-anhydro sugar-cyclopentadiene adducts do not arise from rearrangement of 4 to isolevoglucosenone (5) followed by cycloaddition but are the result of Lewis acid-catalyzed rearrangement of alkene 4 to acyclic dienophile 12 followed by addition of cyclopentadiene. Major cycloadduct 8 has been utilized as a source of the enantiomerically pure carbocycles 14-25 by manipulation of the alkene and ketone functions and cleavage of the 1,6-anhydro bridge. In the absence of diene, alkene 4 undergoes rearrangement to enone 5 in 32% yield. Reaction of 5 with several dienes results only in the formation of "bottom-face" adducts 10, 11, 28, and 29, and conjugate addition of either HN3 or Me3COOH is found to be completely stereoselective to afford 30 and 31, respectively. Subsequent manipulation of azide 30 leads to precursors of several naturally occurring 2-amino-2,3-dideoxy sugars.

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

C-3 epimers of sugar amino acids as foldameric building blocks: improved synthesis, useful derivatives, coupling strategies

To obtain key sugar derivatives for making homooligomeric foldamers or α/β-chimera peptides, economic and multigram scale synthetic methods were to be developed. Though described in the literature, the cost-effective making of both 3-amino-3-deoxy-ribofuranuronic acid (H–tX–OH) and its C-3 epimeric stereoisomer, the 3-amino-3-deoxy-xylofuranuronic acid (H–cX–OH) from d-glucose is described here. The present synthetic route elaborated is (1) appropriate for large-scale synthesis; (2) reagent costs reduced (e.g. by a factor of 400); (3) yields optimized are ~80% or higher for all six consecutive steps concluding –tX– or –cX– and (4) reaction times shortened. Thus, a new synthetic route step-by-step optimized for yield, cost, time and purification is given both for d-xylo and d-ribo-amino-furanuronic acids using sustainable chemistry (e.g. less chromatography with organic solvents; using continuous-flow reactor). Our study encompasses necessary building blocks (e.g. –X–OMe, –X–OiPr, –X–NHMe, Fmoc–X–OH) and key coupling reactions making –Aaa–tX–Aaa– or –Aaa–tX–tX–Aaa– type “inserts”. Completed for both stereoisomers of X, including the newly synthesized Fmoc–cX–OH, producing longer oligomers for drug design and discovery is more of a reality than a wish.

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

Synthesis of oligosaccharide mimetics with glycoaminoxy acids

From readily available di-O-isopropylidene-D-glucose, a Dribofuranoid glycoaminoxy acid and its τBu ester have been efficiently prepared as a new family of sugar building blocks by introducing the phthallmido aminoxy group by a Mitsunobu reaction. We found that the τBu ester can be selectively deprotected with 13.7% TFA in CH2Cl2 at 0°C in the pres-ence of the 1,2-O-isopropylldene acetal. This selective deprotection has made possible the synthesis of homo-oligomers of glycoaminoxy acids (up to six sugar units) as a novel type of oligosaccharide mimetics,