65940-93-4

Usage

Uses

Used in Pharmaceutical Industry:
(6S,3R,3aR,6aR)-6-hydroxy-hexahydrofuro[3,2-b]furan-3-yl acetate is used as a potential pharmaceutical compound for its unique structure and functional groups, which may offer novel therapeutic properties and contribute to the development of new drugs.
Used in Organic Synthesis:
(6S,3R,3aR,6aR)-6-hydroxy-hexahydrofuro[3,2-b]furan-3-yl acetate is used as a building block in organic synthesis for its complex molecular structure, which can be utilized to create a variety of other organic compounds with different applications.
Used in Chemical Research:
(6S,3R,3aR,6aR)-6-hydroxy-hexahydrofuro[3,2-b]furan-3-yl acetate is used as a subject of study in chemical research to better understand its properties, reactivity, and potential applications in various fields, including materials science and biotechnology.

Upstream product

• 108-24-7 acetic anhydride 
• 652-67-5 Isosorbide 
• 50-70-4 D-sorbitol 
• 64-19-7 acetic acid 
• 108-22-5 Isopropenyl acetate 
• 1214839-99-2 (3R,6S)-hexahydrofuro[3,2-b]furan-3,6-diol 
• 108-05-4 vinyl acetate 

Downstream Products

• 16051-77-7 isosorbide-2-mononitrate 
• 111554-46-2 (6S,3R,3aR,6aR)-6-(tosyloxy)-hexahydrofuro[3,2-b]furan-3-yl acetate 
• 186420-34-8 6-amino-O-3-benzoyl-6-deoxy-isosorbide 
• 186420-31-5 2-azido-2-desoxy-5-benzoyl isomannide 
• 109121-52-0 (6S,3R,3aR,6aR)-3-hydroxy-hexahydrofuro[3,2-b]furan-6-yl 4-methylbenzenesulfonate 
• 152963-25-2 (1R,4R,5R,8R)-4-benzylamino-8-methoxy-2,6-dioxabicyclo<3.3.0>octane 
• 152963-26-3 (1R,4R,5R,8R)-4-cyclohexylamino-8-methoxy-2,6-dioxabicyclo<3.3.0>octane 
• 152963-31-0 (1R,4R,5R,8R)-8-benzyloxy-4-cyclohexylamino-2,6-dioxabicyclo<3.3.0>octane 
• 152963-22-9 (1R,4R,5R,8R)-8-benzylamino-2,6-dioxabicyclo<3.3.0>octan-4-ol 
• 152963-27-4 (1R,4R,5R,8R)-4-cyclohexylmethylamino-8-methoxy-2,6-dioxabicyclo<3.3.0>octane 
• 152963-21-8 (1R,4R,5R,8R)-8-cyclohexylamino-2,6-dioxabicyclo<3.3.0>octan-4-ol 
• 111956-66-2 (3R,3aR,6S,6aR)-6-(Benzyloxy)hexahydrofuro[3,2-b]furan-3-ol 
• 162426-82-6 5-O-acetyl-1,4:3,6-dianhydro-2-O-benzyl-D-glucitol 

Relevant academic research and scientific papers

Method for synthesizing isohexitol ester

The invention discloses a method for synthesizing isohexitol ester, which is characterized in that a material containing hexitol and an esterifying agent is contacted with a solid acid catalyst in the presence of an aprotic solvent, and the isohexitol ester is obtained through one-pot one-step reaction. The method is especially suitable for the reaction of directly synthesizing the isohexitol ester, especially isosorbide ester, from hexitol, especially sorbitol, the total yield of the obtained isohexitol ester is 80% or above, and the yield of the isosorbide dicarboxylate reaches 60% or above.

ISOSORBIDE-BASED POLYMETHACRYLATES

A monomer comprises the structure wherein R1 comprises H or a substituted hydrocarbyl or unsubstituted hydrocarbyl, and wherein R2 comprises H, a halide, or a substituted or unsubstituted (C1-C4) hydrocarbyl. A method comprises (a) reacting a dianhydrohexitol precursor having the structure with an acyl-group containing compound having the structure wherein R1 comprises H or a substituted hydrocarbyl or unsubstituted hydrocarbyl, and X comprises a halide, a hydroxyl group, or an acyl group to form an acylated dianhydrohexitol ester intermediate having the structure and (b) reacting the acylated dianhydrohexitol ester intermediate with an acrylic-based compound having the structure wherein R2 comprises H, a halide, or a substituted or unsubstituted (C1-C4) hydrocarbyl, and Y comprises a halide, a hydroxyl group, or an acyl group, to form a dianhydrohexitol-based monomer having the structure

Isohexide hydroxy esters: Synthesis and application of a new class of biobased AB-type building blocks

Here we present the synthesis of a new family of sugar derived 1,4:3,6-dianhydrohexitol based AB-type monomers, containing one methyl ester group and a secondary hydroxyl group in all four possible stereo isomers (RR, RS, SR, SS). Structural characterization of the monomers (5a-d) was established by 1D and 2D NMR analysis, which was further confirmed by single-crystal X-ray structure determination. The application of these monomers in step-growth polymerization afforded fully isohexide based stereo-regular polyesters. Homo polyesters based on the RR and RS monomers were obtained with reasonable molecular weights by melt polymerization (Mn 2400 and 2500 resp.). These materials showed unexpectedly low glass-transition temperatures of 20°C and 15°C respectively. In contrast, the monomers with SR and SS configuration yielded only low molecular weight oligomers. Surprisingly, copolymerization of the RR and SR monomers gave a polyester with higher molecular weight (Mn 4100) and a high Tg of 80°C. These preliminary results show that isohexide hydroxyesters are an intriguing new class of biobased building blocks with many potential applications.

Volatile short-chain amphiphiles derived from isosorbide: Hydrotropic properties of esters vs. ethers

Two series of short-chain isosorbide monoalkanoates, differing from the free hydroxyl position, were synthesized and evaluated as volatile non-ionic hydrotropes, also known as solvo-surfactants . Their aqueous solubilities, solubilizing efficiencies and volatilities were evaluated and compared to the corresponding 5-O-alkylisosorbides. Whatever the acylation position (5-O- or 2-O-), isosorbide monoalkanoates are poorly water-soluble for acyl chains longer than four carbons, whereas 5-O-alkylisosorbides are completely miscible with water up to a pentyl chain, which seems to indicate that an ether link brings more hydrophilicity than an ester bond for these types of molecules. The shorter isosorbide monoalkanoates are completely miscible with water and the butanoates are particularly efficient in terms of aqueous solubilization of hydrophobic compounds. In addition, all hydrotropes exhibit some volatility albeit being non-VOC and contrarily to their ethers homologues, isosorbide alkanoates are easily hydrolysed in basic medium, which suggests a good biodegradability.

PRODUCTION OF 5-MEMBERED AND 6-MEMBERED CYCLIC ESTERS OF POLYOLS

Described herein are improved methods for the preparation of 5- and 6-membered cyclic mono and diesters of sugar alcohols and anhydrosugar alcohols by reaction with an organic acid RCOOH over a solid acidic substrate. The process is adaptable to a continuous process for simultaneously making and separating the cyclic esters from the sugar alcohols and anhydrosugar alcohols under mild conditions using the solid acid substrate as both the catalyst and a chromatographic bed for separation. The reactions are performed at mild temperatures of 700C to 10O0C and the formation of the cyclic esters is nearly quantitative. Also described is a method for making 5- and 6-membered cyclic mono and diesters of sugar alcohols and anhydrosugar alcohols using microwave irradiation in the presence of the organic acid.

Asymmetric synthesis of β-lactams by [2+2] cycloaddition using 1,4:3,6-dianhydro-d-glucitol (isosorbide) derived chiral pools

Highly diastereoselective synthesis of cis-β-lactams via [2+2] cycloaddition reactions of imines derived from a chiral bicyclic aldehyde and ketenes is described. The chiral bicyclic aldehyde as well as chiral acids were prepared from commercially available inexpensive isosorbide. The cycloaddition reaction was found to be highly diastereoselective; in some cases giving a single diastereomer of cis-azetidin-2-one in very good yields. A moderate diastereoselectivity was observed with chiral ketenes derived from isosorbide.

New preparative routes to isosorbide 5-mononitrate

Three new methods for the preparation of the vasodilator isosorbide 5-mononitrate are described. In the first method enzymatic regioselective acetylation of isosorbide gave isosorbide 2-butyrate. Nitration and deprotection of this material afforded isomerically pure isosorbide 5-mononitrate in high overall yield. Secondly, regioselective hydrogenation of isosorbide dinitrate over platinum oxide (PtO2) furnished the 5-mononitrate in 45% yield. Similarly, regioselective reduction of the dinitrate was achieved using sodium borohydride (NaBH4) activated with cobalt or iron phthalocyanine. All three methods show advantages over existing procedures. The Royal Society of Chemistry 2000.

Some Applications of Isopropenyl Acetate to O-, N- and C-Acetylation

New procedure for the preparation of drugs and drug intermediates (isosorbide-5-nitrate, diltiazem) and intermediates of potential drugs using isopropenyl acetate are described.

ESTERIFICATIONS REGIOSELECTIVES DU DIANHYDRO-1,4:3,6-D-GLUCITOL

The 1,4:3,6-dianhydro-D-glucitol was regioselectively esterified at the 2-exo position in order to obtain the 1,4:3,6-dianhydro-5-O-nitro-D-glucitol derivative after nitration and deprotection of the 2-position.Since usual esterification reactions are directed toward the 5-endo position of higher reactivity, due to intramolecular hydrogen bonding and/or chelation involvement with the acylating agent, the selectivity toward the 2-exo position was achieved by preliminary dialkoxidation of the carbohydrate followed by treatment with pivaloyl chloride.

Regioselective Acylation of 1,4:3,6-Dianhydro-D-glucitol

Acylation of 1,4:3,6-dianhydro-D-glucitol with anhydrides in the presence of heavy metal salts affords 5-endo-acylates with high regioselectivity, without detectable amounts of the isomeric 2-acylates.Acyl group migration occurs with preference for the 2-exo-position, on heating an acylation mixture, which contains varying amounts of 1,4:3,6-dianhydro-D-glucitol, 2- and 5-monoacylate and 2,5-diacylate, in the presence of reesterification catalysts and whilst distilling off the lower boiling 2-acylate.