114861-22-2

Usage

Uses

1. Used in Organic Synthesis:
1,2-O-Isopropylidene-a-L-xylofuranose is used as an organic synthesis intermediate for the preparation of various complex organic molecules. Its protected structure allows for selective reactions at specific functional groups, making it a valuable building block in the synthesis of natural products and pharmaceutical compounds.
2. Used in Pharmaceutical Industry:
1,2-O-Isopropylidene-a-L-xylofuranose is used as a pharmaceutical intermediate in the development of new drugs. Its unique structure can be exploited to create novel bioactive molecules with potential therapeutic applications. The compound is particularly useful in the synthesis of glycosides and other carbohydrate-derived pharmaceuticals.
3. Used in Laboratory Research and Development:
1,2-O-Isopropylidene-a-L-xylofuranose is widely used in laboratory research and development processes, where it serves as a key starting material for the synthesis of various target compounds. Its stability and reactivity make it an ideal candidate for exploring new reaction pathways and developing innovative synthetic strategies.
4. Used in Chemical Production Processes:
In the chemical production industry, 1,2-O-Isopropylidene-a-L-xylofuranose is utilized as a key intermediate in the large-scale synthesis of various chemicals and pharmaceuticals. Its protected structure allows for efficient and selective production of desired products, contributing to the overall efficiency of the manufacturing process.

Synthesis

((3aS,5R,6S,6aS)-6-Hydroxy-2,2-dimethyltetrahydrofuro[3,2-d][1,3]dioxol-5-yl)(morpholino)methanone (134). Step 1) (3aS,5S,6R,6aS)-5-(Hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,2-d][1,3]dioxol-6-ol. To a suspension of L-(-)-xylose (133, 19.15 g, 127.5 mmol) and MgSO4 (30.72 g, 255.0 mmol) in acetone (190 mL) was added conc. H2SO4 (1.9 mL) at room temperature. After 12 h, the reaction mixture (all L-(-)-xylose had been consumed) was filtered and the collected solids were washed with acetone (twice, 20 mL per wash). The stirring yellow filtrate was neutralized with NH4OH solution to pH ~ 9. The suspended solids were removed by filtration. The filtrate was concentrated to afford crude bis-acetonide intermediate as yellow oil. The yellow oil was suspended in water (5 mL), and then the pH was adjusted from 9 to 2 with 1 N HCl in water solution. The reaction mixture was stirred for 12 h at room temperature. The resulting mixture was neutralized by the addition of 25% (w/w) K3PO4 in water until pH ~ 7. The mixture was extracted with EtOAc. The organic layer was dried over MgSO4 filtered, and concentrated in vacuo. The crude product was purified by silica gel column chromatography. Yield: (12.63 g, 52%) as yellow oil. 1H NMR (400 MHz, CD3OD) δ 5.88 (d, J = 4.0 Hz, 1H), 4.47 (d, J 4.0 Hz, 1H), 4.18-4.14 (m, 1H), 4.1 1 (d, J = 2.8 Hz, 1H), 3.83-3.71 (m, 2H), 1.45 (s, 3H), 1.29 (s, 3H).

Upstream product

• 131156-47-3 (3aS,3bR,7aS,8aS)-2,2,5,5-tetramethyltetrahydro-3aH-[1,3]dioxolo[4',5':4,5]furo[3,2-d][1,3]dioxane 
• 41546-31-0 L-xylose 
• 67-64-1 acetone 
• 609-06-3 L-xylose 
• 41546-30-9 β-L-arabinose 
• 87-72-9 L-(-)-xylose 
• 58-86-6 D-xylose 
• 87-72-9 L-xylopyranose 
• 87-72-9 D-Xylose 

Downstream Products

• 171720-97-1 (3aS,5S,6R,6aS)-2,2-dimethyl-5-((tosyloxy)methyl)tetrahydrofuro[2,3-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate 
• 218621-71-7 6-hydroxy-2,2-dimethyl-5-(4-methylphenylsulfonyloxymethyl)-(3aS,5S,6R,6aS)-perhydrofuro[2,3-d][1,3]dioxole 
• 120693-81-4 (3aS,5S,6R,6aS)-6-(benzyloxy)-5-((benzyloxy)dimethyl)-2,2-dimethyl-tetrahydro-2H-furo[2,3-d][1,3]dioxole 
• 220827-73-6 5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-L-xylofuranose 
• 166411-39-8 5-O-benzoyl-1,2-O-isopropylidene-7α-L-xylofuranose 
• 155345-99-6 (1S,2R,3S,5S)-7,7-dimethyl-4,6,8-trioxa-3-[(phenylmethoxy)methyl]bicyclo[3.3.0]octan-2-ol 
• 320591-97-7 5-O-(p-chlorobenzoyl)-1,2-O-isopropylidene-α-L-xylofuranose 
• 220827-74-7 (2S,3R,5R)-5-O-(tert-butyldiphenylsilyl)oxymethyl-1,2-O-isopropylidene-2,3-dioxytetrahydrofuran-4-one 
• 377085-07-9 C₂₃H₂₄O₇ 
• 377085-04-6 tert-butyl-(2,2-dimethyl-6-methylene-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy)-diphenyl-silane 
• 377085-05-7 [(3aS,5R,6S,6aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-methanol 
• 3080-30-6 1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-ribofuranose 
• 166411-40-1 5-O-benzoyl-1,2-O-isopropylidene-α-L-erythro-pentofuranose-3-ulose 
• 171866-29-8 1-bromo-2-deoxy-2-β-fluoro-3,5-di-O-benzoyl-α-L-arabinose 

Relevant academic research and scientific papers

Arabinose 5-phosphate analogues as mechanistic probes for Neisseria meningitidis 3-deoxy-d-manno-octulosonate 8-phosphate synthase

3-Deoxy-d-manno-octulosonate 8-phosphate (KDO8P) synthase catalyses the condensation reaction between phosphoenolpyruvate and d-arabinose 5-phosphate (d-A5P) in a key step in lipopolysaccharide biosynthesis in Gram-negative bacteria. The KDO8P synthase from Neisseria meningitidis was cloned into Escherichia coli, overexpressed and purified. A variety of d-A5P stereoisomers were tested as substrates, of these only d-A5P and l-X5P were substrates. The Asn59Ala mutant of N. meningitidis KDO8P synthase was constructed and this mutant retained less than 1% of the wild-type activity. These results are consistent with a catalytic mechanism for this enzyme in which the C2 and C3 hydroxyl groups of d-A5P and Asn59 are critical.

Enantioselective Synthesis of Slagenins A-C

(Matrix Presented) An enantioselective synthesis of slagenins A-C (1a-c) is described in which their absolute stereochemistries were established. The key step in the synthesis involved the efficient condensation of 2-methoxy-dihydro-furan-3-one 9 and urea

Process development of sotagliflozin, a dual inhibitor of sodium- Glucose cotransporter-1/2 for the treatment of diabetes

The development of an efficient manufacturing process for sotagliflozin (LX4211), a dual inhibitor of sodium- glucose cotransporter-1/2 (SGLT-1/2) for the treatment of diabetes, is described. Sotagliflozin features five contiguous chiral centers on the carbohydrate core flanked by a thioether group and a biaryl moiety. Three chiral centers are obtained from the starting material L-xylose, while the other two were established (or modified) via three highly stereoselective transformations: Luche reduction (dr: 97/3), dynamic kinetic resolution of anomeric hemiacetal (dr: 95/5), and Lewis acid-promoted thiolation (dr: 1000/ 1). Global deprotection of the resulting penultimate intermediate with catalytic sodium methoxide followed by recrystallization furnishes sotagliflozin. The longest linear sequence consists of 10 steps from L-xylose with an overall yield of 40%. This process has been performed on multi-hundred kilogram batches to satisfy the drug substance development demands.

METHOD FOR PRODUCING DIPHENYLMETHANE DERIVATIVE

The present invention relates to an improved method for producing a diphenylmethane derivative which is effective as a sodium-dependent glucose cotransporter (SGLT) inhibitor, the method being carried out by means of a convergent synthesis method in which

Total Synthesis of 5-Hydroxygoniothalamin

The total synthesis of 5-hydroxygoniothalamin is achieved from commercially available l -xylose. The α,β-unsaturated-δ-lactone core is constructed in very good yield by utilizing one-carbon and two-carbon cis -Wittig olefinations and δ-lactonization using Yamaguchi conditions. Subsequent Grubbs cross-metathesis followed by desilylation results in 5-hydroxygoniothalamin.

Novel synthesis method of furan xylose derivatives

The invention discloses a novel synthesis method of furan xylose derivatives, which comprises the following steps: L-(-) xylose and acetone are used as starting materials, and only 2-5 equivalents ofacetone are needed under the catalysis of acholine chlor

COMPOSITIONS COMPRISING (2S,3R,4R,5S,6R)-2-(4- CHLORO-3-(4-ETHOXYBENZYL)PHENYL)-6-(METHYLTHIO)TETRAHYDRO-2H-PYRAN-3,4,5-TRIOL

Pharmaceutical dosage forms useful for improving the cardiovascular and/or metabolic health of patients, particularly those suffering from type 2 diabetes, are disclosed, as well as methods of their manufacture.

Glucopyranosyl derivative and application thereof in medicine

The invention relates to a glucopyranosyl derivative as a sodium-dependent glucose transporter (SGLT) inhibitor, a pharmaceutical composition containing the derivative and an application thereof in medicine, and in particular to the glucopyranosyl derivative as shown in a formula (I) or a pharmaceutically acceptable salt or all stereisomers thereof, or use of the pharmaceutical composition containing the derivative and the derivative and the pharmaceutical composition for preparing medicines treating diabetes and diabetes related diseases.

METHOD FOR PREPARING DIPHENYLMETHANE DERIVATIVES

The present invention relates to an improved process for preparing a diphenyl methane derivative which is useful as an inhibitor of a sodium-dependent glucose transporter (SGLT). Since the process of the present invention is performed by convergent synthe

Larger laboratory scale synthesis of 5-methyluridine and formal synthesis of its L-enantiomer

A larger laboratory scale synthesis (>60 g per run) of 5-methyluridine is presented. The critical intermediate 1,2-O-isopropylidene-α-D-ribofuranose was prepared from very cheap D-glucose via D-allose. Its L-enantiomer was obtained from L-arabinose via L-glucose, and also from L-xylose. {figure presented}.