62133-03-3

Usage

Uses

Used in Organic Synthesis:
1,2:4,6-Di-O-isopropylidene-L-sorbofuranose is used as a synthetic intermediate for the synthesis of various complex organic compounds. Its unique structural features, including the isopropylidene groups, make it a versatile building block for creating a wide range of molecules with potential applications in different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1,2:4,6-Di-O-isopropylidene-L-sorbofuranose is used as a key component in the development of novel drug candidates. Its ability to participate in various chemical reactions allows for the creation of new molecules with potential therapeutic properties.
Used in Chemical Research:
1,2:4,6-Di-O-isopropylidene-L-sorbofuranose is also used in chemical research as a model compound to study the properties and reactivity of similar structures. This helps researchers gain a better understanding of the underlying chemical principles and develop new strategies for synthesizing complex molecules.
Used in Material Science:
In the field of material science, 1,2:4,6-Di-O-isopropylidene-L-sorbofuranose can be used to develop new materials with specific properties. Its unique structure can be exploited to create materials with tailored characteristics, such as improved stability or enhanced reactivity.

Upstream product

• 470-15-5 α-L-sorbopyranose 
• 22665-67-4 2-methoxyisobutanol 
• 7270-77-1 L-sorbopyranose 
• 35673-97-3 L-sorbose 
• 77-76-9 2,2-dimethoxy-propane 
• 67-64-1 acetone 
• 18604-19-8 11,2:4,6-di-O-isopropylidene-α-L-sorbofuranose 
• 87-79-6 L-sorbose 
• 41847-02-3 L-sorbose 

Downstream Products

• 1438263-47-8 (E)-3,4,6-tri-O-benzyl-l-xylo-hex-2-ulose methyloxime 
• 1438263-48-9 (Z)-3,4,6-tri-O-benzyl-l-xylo-hex-2-ulose methyloxime 
• 1438263-49-0 (E)-3,4,6-tri-O-benzyl-l-xylo-Hex-2-ulose tertiobutyldiphenylsilyloxime 

Relevant academic research and scientific papers

Scalable, efficient and rapid chemical synthesis of L-Fructose with high purity

An improved process for chemical synthesis of L-fructose with high purity in large scale from readily available L-sorbose is described. In general, this synthetic scheme is characterized by inexpensive and easily available starting materials, simple and s

Stereoselective synthesis of (2S,3S,4R,5S)-3,4-dihydroxy-2,5- dihydroxymethyl pyrrolidine from l-sorbose

One of the most frequently synthesized iminosugar derivatives is DMDP. Starting from l-sorbose, a practical method for the synthesis of derivatives of this five-membered iminocyclitol has been developed, involving straightforward steps and a convenient selective reduction of a ketoxime intermediate.

A reinvestigation of the synthesis and revision of spectral data of 1,2-O-isopropylidene-α-l-sorbofuranose, 1,2:4,6-di-O-isopropylidene- α-l-sorbofuranose and derivatives

Mono- and di-O-isopropylidene-l-sorbofuranose derivatives are important starting materials for the synthesis of modified sugars and useful chiral compounds. However, several inconsistencies in the spectral data of these compounds and erroneous structural assignments have been noted in the literature. The unambiguous synthesis of 1,2:4,6-di-O-isopropylidene-α-l- sorbofuranose and derivatives of 1,2- and 2,3-O-isopropylidene-α-l- sorbofuranoses has been achieved and definitive spectral data on these compounds are provided.

Large-scale synthesis of the glucosylceramide synthase inhibitor N-[5-(adamantan-1-yl-methoxy)-pentyl]-1-deoxynojirimycin

A synthetic route for the preparation of glucosylceramide synthase inhibitor N-[5-(adamantan-1-yl-methoxy)-pentyl]-1-deoxynojirimycin methanesulfonic acid salt (AMP-DNM) has been developed. Herein we report the development and optimization of this synthetic route from its initial version in an academic research laboratory at milligram-scale to the final optimized route that was implemented in a cGMP miniplant on kilogram-scale. The definitive route starts with the separate synthesis of building blocks 2,3,4,6-tetra-O- benzyl-1-deoxynojirimycin and 5-(adamantan-1-ylmethoxy)-pentanal. The aldehyde was synthesized from 1,5-pentanediol in five steps and 45% overall yield. Protected 1-deoxynojirimycin was prepared by a successive hemiacetal reduction/Swern oxidation/double reductive amination sequence of 2,3,4,5-tetra-O-benzyl-D-glucopyranose in 52% overall yield. Reductive amination of the two building blocks produced the benzylprotected penultimate that was isolated as its crystalline (+)DTTA salt in 68% yield. Hydrogenolysis of the penultimate and crystallization of the end product as its methanesulfonic acid salt produced AMP-DNM in 76% yield with a purity of >99.5%. The described route enables the production of multikilogram amounts of inhibitor AMP-DNM as a stable crystalline solid with high purity under cGMP control.

Sulfuric acid immobilized on silica: an efficient reusable catalyst for the synthesis of O-isopropylidene sugar derivatives

Sulfuric acid immobilized on silica proved to be an efficient catalyst for the synthesis of O-isopropylidene sugar derivatives from reducing sugars. The method is very simple and economic for large-scale synthesis in which the catalyst is recovered and reused several times. Reactions with d-glucose, d-galactose, d-mannose, l-rhamnose, l-arabinose, d-xylose and l-sorbose led to the formation of the corresponding thermodynamically stable di-O- and/or mono-O-isopropylidene derivatives in good to excellent yields.

Practical synthesis of an L-fructose-derived ketone catalyst for asymmetric epoxidation of olefins

An L-fructose-derived ketone catalyst for asymmetric epoxidation of trans- and tri substituted olefins was efficiently prepared from L-sorbose in five steps.

Catalytic asymmetric epoxidation

A compound and method for producing an enantiomerically enriched epoxide from an olefin using a chiral ketone and an oxidizing agent is disclosed.

Photochemical deconjugation of chiral 3-methyl-2-butenoates derived from carbohydrate-based alcohols: The influence of the sugar backbone on the facial diastereoselectivity

The photodeconjugation of the α-(4-trimethylsilyl-3-butynyl)-substituted senecio acid esters 7 was studied. Chiral alcohols ROH (9) were employed as auxiliaries to control the facial diastereoselectivity of the protonation step. The conversion of the four sugar alcohols diacetone-D-glucofuranose, diacetone-D-allofuranose, diacetone-D-gulofuranose, and diacetone-D-fructopyranose (9a-d) to the esters 7 was achieved in four steps employing 4-iodo-1-trimethylsilylbut-1-yne (3) as the alkylating agent (27-45% yield overall). Their photodeconjugation gave the corresponding β,γ-unsaturated (R)-esters 14a-d with moderate to excellent diastereomeric excess. The best results were achieved with diacetone-D-glucofuranose and diacetone-D-fructopyranose as the auxiliary (>95% de). To achieve the synthesis of the target compound 1 which has the (S)-configuration, the deconjugation was conducted with the diacetone-L-fructopyranose (ent-9d) derived ester ent-7d. L-Fructose (20) was prepared from L-sorbose (15) in a modified procedure that allowed for the isolation of intermediates. The 2-fold inversion of configuration worked nicely, and the fructofuranose 19 was obtained in 19% yield from L-sorbose. The conversion of L-fructose to the ester ent-7d was conducted in full analogy to the synthesis of its enantiomer 7d. Deconjugation of ester ent-7d yielded the product 2d (70% yield), which was reduced to the alcohol 1 (85% yield).

An efficient catalytic asymmetric epoxidation method

This article describes a highly effective catalytic asymmetric epoxidation method for olefins using,potassium peroxomonosulfate (Oxone, Dupont) as oxidant and a fructose-derived ketone(l) as catalyst. High enantioselectivies have been obtained-for trans-disubstituted and trisubstituted olefins which can bear functional groups such as tributylsilyl ether, acetal, chloride, and ester. The enantiomeric excesses cis-olefins and terminal olefins are not high yet. The current epoxidation shows that the catalyst efficiency is enhanced dramatically-upon raising the pH. Mechanitic studies show that the epoxidation mainly proceeds via a spiro transition state, which provides a model for predicting the stereochemical outcome of the reaction. The planar transition state, likely to be the main competing pathway. The extent of the involvement of the planar mode is subject to the steric of the alkyl groups on the olefins.

Synthesis of 1,5-dideoxy-1,5-imino-D-galactitol fromL-sorbose

A facile new synthesis of 1-deoxygalactonojirimycin (1) [1,5-dideoxy-1,5-imino-D-galactitol] is described. The L-sorbose derivative (15) is epimerised at C-3 and converted, via the L-tagatofuranose (18) into the deoxyazide (20). Reduction of azide (20) and deprotection affords 1-deoxygalactonojirimycin (1).