34685-42-2

Usage

Uses

Used in Organic Synthesis:
2,3:5,6-Di-O-isopropylidene-D-gulofuranose is used as a protective group for alcohols in organic synthesis, allowing for selective reactions to occur. This application is crucial for the controlled synthesis of complex organic molecules and the development of new drugs and materials.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,3:5,6-Di-O-isopropylidene-D-gulofuranose is used as a key intermediate in the synthesis of various pharmaceuticals. Its ability to act as a protective group for alcohols facilitates the production of complex drug molecules with specific functionalities and improved therapeutic properties.
Used in Agrochemical Industry:
2,3:5,6-Di-O-isopropylidene-D-gulofuranose is also utilized in the agrochemical industry for the synthesis of agrochemicals, such as pesticides and herbicides. Its role in protecting alcohol groups during organic synthesis contributes to the development of effective and targeted agrochemicals with minimal environmental impact.
Used in Natural Product Synthesis:

Upstream product

• 3458-28-4 D-Mannose 
• 77-76-9 2,2-dimethoxy-propane 
• 67-64-1 acetone 
• 530-26-7 D-Mannose 
• 116-11-0 2-Methoxypropene 
• 50-81-7 ascorbic acid 
• 1128-23-0 L-gulono-1,4-lactone 
• 7306-64-1 2,3:5,6-di-O-isopropylidene-L-gulonolactone 
• 49561-21-9 (3aR,6S,6aR)-6-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one 
• 75-52-5 nitromethane 
• 5328-37-0 L-arabinose 
• 582-52-5 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 138034-65-8 (1R)-2,3-5,6-di-O-isopropylidene-1-C-phenyl-D-mannitol 
• 138034-65-8 (R)-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)((4S,5R)-5-((S)-hydroxy (phenyl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol 
• 7306-64-1 2,3:5,6-di-O-isopropylidene-α-D-mannono-1,4-lactone 
• 157309-47-2 Acetic acid (R)-[(4R,5R)-5-((1R,2R)-1-acetoxy-2,3-dihydroxy-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-phenyl-methyl ester 
• 157309-46-1 Acetic acid (R)-[(4R,5R)-5-((R)-acetoxy-phenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl ester 
• 162808-23-3 (3aS,4R,6S,6aR)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-phenyltetrahydrofuro[3,4-d][1,3]dioxole 
• 157309-48-3 (Z)-(R)-4-Acetoxy-4-[(4S,5R)-5-((R)-acetoxy-phenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-but-2-enoic acid methyl ester 
• 76679-45-3 Benzyl-2,3-di-O-benzyl-5-O-(2,3:5,6-di-O-isopropyliden-β-D-mannofuranosyl)-β-D-ribofuranosid 
• 76679-42-0 Benzyl-2,3-di-O-benzyl-5-O-(2,3:5,6-di-O-isopropyliden-α-D-mannofuranosyl)-β-D-ribofuranosid 
• 17087-84-2 (3aS,4R,6R,6aS)-4-chloro-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole 
• 94898-41-6 (3aS,4R,6R,6aS)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-fluoro-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxole 
• 79241-07-9 (R)-4-((2S,3R)-3-(benzyloxy)-2,3-dihydrofuran-2-yl)-2,2-dimethyl-1,3-dioxolan 
• 7306-64-1 2,3,5,6-di-O-isopropylidene-D-mannono-1,4-lactone 
• 869354-98-3 benzyl 2,3: 5,6-di-O-isopropylidene-D-mannofuranoside 

Relevant academic research and scientific papers

Total Synthesis of 6-Amino-2,6-dideoxy-α-Kdo from d -Mannose

3-Deoxy-d-manno-oct-2-ulosonic acid (Kdo) biosynthetic pathway is a promising target in antibacterial drug discovery. Herein, we report the total synthesis of 6-amino-2,6-dideoxy-α-Kdo in 15 steps from d-mannose as a potential inhibitor of Kdo-processing

Synthesis of Galactosyl-Queuosine and Distribution of Hypermodified Q-Nucleosides in Mouse Tissues

Queuosine (Q) is a hypermodified RNA nucleoside that is found in tRNAHis, tRNAAsn, tRNATyr, and tRNAAsp. It is located at the wobble position of the tRNA anticodon loop, where it can interact with U as well as C bases located at the respective position of the corresponding mRNA codons. In tRNATyr and tRNAAsp of higher eukaryotes, including humans, the Q base is for yet unknown reasons further modified by the addition of a galactose and a mannose sugar, respectively. The reason for this additional modification, and how the sugar modification is orchestrated with Q formation and insertion, is unknown. Here, we report a total synthesis of the hypermodified nucleoside galactosyl-queuosine (galQ). The availability of the compound enabled us to study the absolute levels of the Q-family nucleosides in six different organs of newborn and adult mice, and also in human cytosolic tRNA. Our synthesis now paves the way to a more detailed analysis of the biological function of the Q-nucleoside family.

Discovery and Structure-Activity Relationships of Novel Template, Truncated 1′-Homologated Adenosine Derivatives as Pure Dual PPARγ/δModulators

Following our report that A3 adenosine receptor (AR) antagonist 1 exhibited a polypharmacological profile as a dual modulator of peroxisome proliferator-activated receptor (PPAR)γ/δ, we discovered a new template, 1′-homologated adenosine analogues 4a-4t, as dual PPARγ/δmodulators without AR binding. Removal of binding affinity to A3AR was achieved by 1′-homologation, and PPARγ/δdual modulation was derived from the structural similarity between the target nucleosides and PPAR modulator drug, rosiglitazone. All the final nucleosides were devoid of AR-binding affinity and exhibited high binding affinities to PPARγ/δbut lacked PPARα binding. 2-Cl derivatives exhibited dual receptor-binding affinity to PPARγ/δ, which was absent for the corresponding 2-H derivatives. 2-Propynyl substitution prevented PPARδ-binding affinity but preserved PPARγaffinity, indicating that the C2 position defines a pharmacophore for selective PPARγligand designs. PPARγ/δdual modulators functioning as both PPARγpartial agonists and PPARδantagonists promoted adiponectin production, suggesting their therapeutic potential against hypoadiponectinemia-associated cancer and metabolic diseases.

Straightforward synthesis of protected 2-hydroxyglycals by chlorination-dehydrochlorination of carbohydrate hemiacetals

A straightforward and scalable method for the synthesis of protected 2-hydroxyglycals is described. The approach is based on the chlorination of carbohydrate-derived hemiacetals, followed by an elimination reaction to establish the glycal moiety. 1,2-dehy

PHARMACEUTICAL COMPOSITION FOR PREVENTING AND TREATING GLAUCOMA, CONTAINING ADENOSINE DERIVATIVE

A pharmaceutical composition for preventing or treating eye diseases and an oral administration agent for preventing or treating eye diseases are provided. The pharmaceutical composition for preventing or treating eye diseases comprises the compound repre

Compound, preparation method and applications thereof, and glycosidase inhibitor

The invention relates to the field of enzyme inhibitors, and discloses a compound, a preparation method and applications thereof, and a glycosidase inhibitor, wherein the compound has a structure represented by a formula (I), R is any one selected from hy

Synthesis of Butenolides via a Horner-Wadsworth-Emmons Cascading Dimerization Reaction

The efficient synthesis of a range of structurally related butenolides has been observed while we were exploring the substrate-scope of a Horner-Wadsworth-Emmons (HWE) reaction. While aliphatic aldehydes gave the expected HWE product, aromatic aldehydes f

PHARMACEUTICAL COMPOSITION FOR PREVENTING AND TREATING NONALCOHOLIC STEATOHEPATITIS, HEPATIC FIBROSIS, AND LIVER CIRRHOSIS, COMPRISING ADENOSINE DERIVATIVES

A pharmaceutical composition for preventing or treating liver disease is provided. The pharmaceutical composition comprising a compound represented by formula 1 below or a pharmaceutically acceptable salt of the compound as an active ingredient: where A i

Synthesis of triazolylmethyl-linked nucleoside analogs via combination of azidofuranoses with propargylated nucleobases and study on their cytotoxicity

[Figure not available: see fulltext.] Copper(I)-catalyzed azide–alkyne 1,3-dipolar cycloaddition reactions (CuAAC) between azidofuranoses and propargyl-nucleobases were carried out in the presence of CuSO4·5H2O and sodium ascorbate as catalytic system to provide the corresponding 1,4-disubstituted-1,2,3-triazole-bridged nucleoside analogs in good yields. Twelve new sugar-based triazolylmethyl-linked nucleoside analogs were synthesized and screened for their cytotoxic activity against MDA-MB-231, Hep3B, PC-3, SH-SY5Y, and HCT-116 cancer cell lines and control cell line (L929). Most of the compounds were moderately effective against all the cancer cell lines assayed. Particularly, among the tested compounds, 1,2,3-triazole-linked 5-fluorouracil–mannofuranose hybrid was found to be the most potent cytotoxic agent against HCT-116, Hep3B, SH-SY5Y cells with IC50 values of 35.6, 71.1, and 75.6 μM, respectively. None of the triazolylmethyl-linked nucleoside analogs exhibited cytotoxic effect against the control cells L929.

Undemanding Synthesis of Novel C19 and C17 Analogues of C18-Guggultetrol

A simple and undemanding synthesis of (2S,3R,4R,5R)-nonadecane-1,2,3,4,5-pentol and (2S,3R)-heptadecane-1,2,3-triol as novel C19 and C17 analogues of C18-guggultetrol was achieved by using l-ascorbic acid as a chiral pool.