18039-26-4

Usage

Uses

Used in Organic Synthesis:
2,3,4-Tri-O-benzyl-beta-D-arabinopyranose is used as a protecting group in organic synthesis for the hydroxyl functionalities of sugars. This application is crucial for enabling selective reactions at other positions on the sugar molecule, which is essential for the synthesis of complex organic compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,3,4-Tri-O-benzyl-beta-D-arabinopyranose is utilized as a building block in the synthesis of complex natural products and pharmaceuticals. Its ability to be selectively deprotected under mild conditions allows for the creation of a wide range of bioactive compounds with potential therapeutic applications.
Used in Chemical Research:
2,3,4-Tri-O-benzyl-beta-D-arabinopyranose is also used in chemical research for the development of new synthetic methods and the exploration of novel chemical reactions. Its versatility as a protecting group and building block makes it an invaluable tool for researchers working on the frontiers of organic chemistry.

InChI:InChI=1/C26H28O5/c27-26-25(30-18-22-14-8-3-9-15-22)24(29-17-21-12-6-2-7-13-21)23(19-31-26)28-16-20-10-4-1-5-11-20/h1-15,23-27H,16-19H2

Upstream product

• 1338567-54-6 C₂₈H₂₉Cl₃O₅ 
• 134149-46-5 (3R,4S,5S)-3,4,5-Tris-benzyloxy-2-[((E)-propenyl)oxy]-tetrahydro-pyran 
• 87908-25-6 2-methoxyethyl 2,3,4-tri-O-benzyl-α-L-arabinopyranoside 
• 87-72-9 L-(+)-arabinose 
• 100-44-7 benzyl chloride 
• 52544-91-9 phenyl 2,3,4-tri-O-acetyl-1-thio-α-L-arabinopyranoside 
• 1352718-30-9 C₁₁H₁₄O₄S 
• 1352718-31-0 C₃₂H₃₂O₄S 
• 1233-03-0 1,2,3,4-tetra-O-acetyl-L-arabinopyranose 
• 5328-37-0 L-arabinose 
• 100-39-0 benzyl bromide 
• 87908-24-5 2-methoxyethyl 2,3,4-tri-O-benzyl-β-D-xylopyranoside 
• 64-19-7 acetic acid 
• 196859-51-5 (2,3-dibenzyloxypropyl) 2,3,4-tri-O-benzyl-α-D-xylopyranoside 

Downstream Products

• 209125-48-4 (3R,4S,5S)-3,4,5-Tris-benzyloxy-tetrahydro-pyran-2-one 
• 21401-20-7 UDP-arabinose 
• 2405-69-8 2,3,4-tri-O-benzyl-L-arabinitol 
• 1227291-94-2 C₂₇H₃₁NO₅ 
• 130931-48-5 C₂₇H₃₀O₄ 
• 1092684-39-3 (2S,3S,4R)-2-(hexacosanamido)-1-O-(2,3,4-tri-O-benzyl-β-L-arabinopyranosyl)octadecane-1,3,4-triol 
• 1093738-70-5 1-O-acetyl 2,3,4-tri-O-benzyl-α,β-L-arabinopyranose 
• 1427178-87-7 N-benzyloxycarbonyl 2,3,4-tri-O-benzyl-α-L-arabinopyranosylamine 
• 1427178-88-8 N-benzyloxycarbonyl 2,3,4-tri-O-benzyl-β-L-arabinopyranosylamine 

Relevant academic research and scientific papers

Synthesis of Glycosyl Fluorides by Photochemical Fluorination with Sulfur(VI) Hexafluoride

This study describes a new convenient method for the photocatalytic generation of glycosyl fluorides using sulfur(VI) hexafluoride as an inexpensive and safe fluorinating agent and 4,4′-dimethoxybenzophenone as a readily available organic photocatalyst. This mild method was employed to generate 16 different glycosyl fluorides, including the substrates with acid and base labile functionalities, in yields of 43%-97%, and it was applied in continuous flow to accomplish fluorination on an 7.7 g scale and 93% yield.

TRITERPENE SAPONIN SYNTHESIS, INTERMEDIATES AND ADJUVANT COMBINATIONS

The present application relates to triterpene glycoside saponin-derived adjuvants, syntheses thereof, and intermediates thereto. The application also provides pharmaceutical compositions comprising compounds of the present invention and methods of using said compounds or compositions in the treatment of and immunization for infectious diseases.

Ring-opened 4-hydroxy-δ-valerolactone subunit as a key structural fragment of polyesters that degrade without acid formation

Random copolymers of ?-caprolactone with O-benzyl-protected 4-hydroxy- or 2,4-dihydroxy-δ-valerolactone after hydrogenation form γ-hydroxy functionalized polyesters that degrade via the cyclization to γ-butyrolactone fragments without carboxylic acid formation.

Synthesis of Phenolic Glycosides: Glycosylation of Sugar Lactols with Aryl Bromides via Dual Photoredox/Ni Catalysis

Multifarious sugar lactols were efficiently transformed into the corresponding phenolic glycosides by treating with aryl bromides in acetonitrile with Ir[dF(CF3)ppy]2(dtbbpy)(PF6) as a photocatalyst under visible light irr

Intramolecular Tandem Seleno-Michael/Aldol Reaction: A Simple Route to Hydroxy Cyclo-1-ene-1-carboxylate Esters

Intramolecular tandem seleno-Michael/aldol reaction followed by an oxidation-elimination process can be an efficient tool for the construction of hydroxy cyclo-1-ene-1-carboxylate esters from oxo-α,β-unsaturated esters. Generation of lithium selenolate from elemental selenium and n-BuLi provides a simple and efficient one-pot access to cyclic endo-Morita-Baylis-Hillman adducts.

A Kinsenoside and GoodyerosideA analogs of the preparation and use thereof

The invention discloses a preparation method and application of compounds as shown in formula I and II, and in particular relates to preparation of Kinsenoside or GoodyerosideA analogue and medical application of the Kinsenoside or GoodyerosideA analogue

Automated glycan assembly of xyloglucan oligosaccharides

We report the automated glycan assembly of oligosaccharide fragments related to the hemicellulose xyloglucan (XG). Iterative addition of monosaccharide and disaccharide building blocks to a solid support provided seven cellulose and xyloglucan fragments i

Glucosylceramide mimics: Highly potent GCase inhibitors and selective pharmacological chaperones for mutations associated with types 1 and 2 gaucher disease

A series of iminoxylitol derivatives carrying a C-linked di-O-acyl or di-O-alkyl glyceryl substituent were prepared and characterized. All of these compounds, which were designed as glucosylceramide (GlcCer) mimics, were nanomolar inhibitors of lysosomal b-glucosidase (glucocerebrosidase, GCase). Two of these pseudoglycolipids were further evaluated for their ability to enhance the activity of mutant GCase in human Gaucher cells. Although the di-O-hexyl ether was surprisingly devoid of chaperoning activity on both N370S and L444P GCases, the di-Odecanoyl ester was a potent chaperone of the L444P hydrolase, capable of increasing the residual activity of the enzyme by a factor of two at a very low concentration (50 nm); such a significant effect on the L444P mutation in human fibroblasts has not yet been observed. In heat-stress studies, the diether was found to be much more effective in stabilizing the wildtype enzyme than the diester. Four representative pseudoglycolipids were also assayed as inhibitors of GlcCer synthase, because such compounds could find use in the substrate reduction therapy approach to treat lysosomal storage diseases, but these compounds revealed only moderate activity. As efficient pharmacological chaperones, new structures such as the di-C10-ester constitute leads for the development of therapeutic agents for types 2 and 3 Gaucher disease, the most severe neuronopathic forms of this lysosomal disease.

An improved methodology for the synthesis of 1-C-allyl imino-d-xylitol and -l-arabinitol and their rapid functionalization

As part of our research program dedicated to the design and synthesis of new iminosugars as pharmacological chaperones for the treatment of lysosomal storage disorders, we developed a rapid and efficient methodology for the access to functionalized and no

RCAI-61 and related 6′-modified analogs of KRN7000: Their synthesis and bioactivity for mouse lymphocytes to produce interferon-γ in vivo

We synthesized ten new analogs of 6′-modified KRN7000 (A): RCAI-58, 61, 64, 83, 85-87, 113, 119, and 125. They could be synthesized by α-selective galactosylation of ceramide 9 with the 6-modified d-galactopyranosyl fluorides (8a-8f) or l-arabinopyranosyl