108740-74-5

Basic information

• Product Name: Phenyl 2,3,4-Tri-O-acetyl-1-thio-α-L-rhamnopyranoside
• Synonyms: Phenyl 2,3,4-Tri-O-acetyl-1-thio-α-L-rhamnopyranoside;Phenyl 6-Deoxy-1-thio-α-L-Mannopyranoside Triacetate
• CAS NO: 108740-74-5
• Molecular Formula: C₁₈H₂₂O₇S
• Molecular Weight: 382.42808
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives;Sulfur & Selenium Compounds
• Mol File: 108740-74-5.mol

Chemical Properties

• Melting Point: 106-109°C
• Appearance: /
• Solubility: Dichloromethane, Ethyl Acetate, Methanol
• CAS DataBase Reference: Phenyl 2,3,4-Tri-O-acetyl-1-thio-α-L-rhamnopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Phenyl 2,3,4-Tri-O-acetyl-1-thio-α-L-rhamnopyranoside(108740-74-5)
• EPA Substance Registry System: Phenyl 2,3,4-Tri-O-acetyl-1-thio-α-L-rhamnopyranoside(108740-74-5)

Safety Data

• Hazardous Substances Data: 108740-74-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Phenyl 2,3,4-Tri-O-acetyl-1-thio-α-L-rhamnopyranoside is used as an intermediate in organic synthesis for the preparation of various complex organic molecules. Its unique structure allows for selective functionalization and modification, making it a versatile building block for the synthesis of a wide range of compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Phenyl 2,3,4-Tri-O-acetyl-1-thio-α-L-rhamnopyranoside is used as a key intermediate in the synthesis of glycoconjugate drugs. These drugs have the potential to target specific biological receptors, making them valuable for the development of targeted therapeutics. The compound's unique structure allows for the introduction of various functional groups, enabling the creation of novel drug candidates with improved pharmacological properties.
Used in Chemical Research:
Phenyl 2,3,4-Tri-O-acetyl-1-thio-α-L-rhamnopyranoside is also used as a research tool in the field of chemical research. Its unique structure and reactivity make it an ideal candidate for studying various chemical reactions and mechanisms, such as glycosylation, acetylation, and other carbohydrate-related reactions. This research can lead to a better understanding of carbohydrate chemistry and the development of new synthetic strategies and methodologies.
Used in Material Science:
In the field of material science, Phenyl 2,3,4-Tri-O-acetyl-1-thio-α-L-rhamnopyranoside can be used as a building block for the development of novel materials with specific properties. Its unique structure and functional groups can be exploited to create materials with tailored properties, such as improved solubility, stability, or biocompatibility. These materials can find applications in various industries, including pharmaceuticals, cosmetics, and biotechnology.

Upstream product

• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-rhamnopyranose 
• 4551-15-9 phenylthiotrimethylsilane 
• 108-98-5 thiophenol 
• 882-33-7 diphenyldisulfane 
• 5158-64-5 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl bromide 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 106929-82-2 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranose 
• 930-69-8 sodium thiophenolate 
• 28915-80-2 2,3,4-tri-O-acetyl-L-rhamnopyranose 
• 73-34-7 L-rhamnose 
• 108-24-7 acetic anhydride 
• 39524-38-4 2,3,4-tri-O-acetyl-6-deoxy-beta-L-mannopyranosyl bromide 
• 30021-94-4 1,2,3,4-O-tetraacetyl-α-L-rhamnopyranose 
• 3615-41-6 L-Rhamnose 

Downstream Products

• 131897-04-6 phenyl 2,3,4-tri-O-benzyl-1-thio-α-L-rhamnopyranoside 
• 314263-97-3 (E)-p-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyloxy)-β-nitrostyrene 
• 130851-56-8 methyl 4-<<3-O-methyl-α-L-rhamnopyranosyl>oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoate 
• 131675-54-2 phenyl 3-O-methyl-1-thio-α-L-rhamnopyranoside 
• 131675-55-3 phenyl 2,4-di-O-acetyl-3-O-methyl-1-thio-α-L-rhamnopyranoside 
• 131675-57-5 methyl 4-<<2,4-di-O-acetyl-3-O-methyl-α-L-rhamnopyranosyl>oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoate 
• 131675-59-7 4-<<3-O-methyl-2,4-bis-O-(triethylsilyl)-α-L-rhamnopyranosyl>oxy>-5-iodo-2,3-dimethoxy-6-methylbenzyl alcohol 
• 129834-74-8 4-<<3-O-methyl-2,4-bis-O-(triethylsilyl)-α-L-rhamnopyranosyl>oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoic acid 
• 131675-58-6 methyl 4-<<3-O-methyl-2,4-bis-O-(triethylsilyl)-α-L-rhamnopyranosyl>oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoate 
• 55836-48-1 2,4-di-O-acetyl-3-O-methyl-β-L-rhamnopyranose 
• 150738-45-7 2,4-di-O-acetyl-3-O-methyl-α-L-rhamnopyranose 
• 146399-77-1 phenyl 4-O-benzyl-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside 
• 146399-74-8 phenyl 4-O-benzyl-1-thio-α-L-rhamnopyranoside 

Relevant articles and documents

Slow glycosylation: Activation of trichloroacetimidates under mild conditions using lithium salts and the role of counterions

Glycosylations were carried out with the two glycosyl donors 4-O-acetyl-2,3-O-isopropylidene-1-O-trichloroacetimidoyl-α-L-rhamnopyranose and 2,3,4-tri-O-benzyl-1-O-trichloro-acetimidoyl-α-L-rhamnopyranose in combination with the two alcohols 1-adamantanol and L-menthol as model glycosyl acceptors. As catalysts, the five lithium salts LiNTf2, LiI, LiClO4, LiPF6 and LiOTf were investigated. We demonstrated that both lithium and the respective counterions are playing a role in the activation of trichloroacetimidate glycosyl donors at rt. Under these very mild conditions, the glycosylations are slow and completed in two to eight days. Depending on the counterion, the rate and yield of the reaction differs; however, the selectivity of all investigated lithium salts is deficient.

Concise Synthesis of 1-Thioalkyl Glycoside Donors by Reaction of Per-O-acetylated Sugars with Sodium Alkanethiolates under Solvent-Free Conditions

A relatively green method for synthesizing 1-thioalkyl glycosides has been developed, where sodium alkanethiolates were used to react with per-O-acetylated sugars instead of odorous alkyl mercaptans in the presence of BF3·Et2O without the use of solvents under mild conditions. Furthermore, we found that 1,2-trans-β-thioglycosides can be converted into corresponding 1,2-cis-α-thioglycosides in the presence of trifluoromethanesulfonic acid in nonpolar solvents under mild conditions. This provides a simple and efficient new approach for synthesizing challenging 1,2-cis-α-thioglycosides.

Transition-metal-free synthesis of aryl 1-thioglycosides with arynes at room temperature

A mild, convenient and transition-metal-free protocol for the synthesis of aryl 1-thioglycosides is presentedviaarynes generatedin situcombined with glycosyl thiols in the presence of TBAF(tBuOH)4. The methodology provides a general and efficient way to prepare a series of functionalized thioglycosides in good to excellent yields with a perfect control of the anomeric configuration at room temperature. In addition, the reaction conditions tolerate a variety of the pentoses and hexoses, and the reaction also performs smoothly on protected monosaccharides and disaccharides.

Synthesis of Cardiotonic Steroids Oleandrigenin and Rhodexin B

This article describes a concise synthesis of cardiotonic steroids oleandrigenin (7) and its subsequent elaboration into the natural product rhodexin B (2) from the readily available intermediate (8) that could be derived from the commercially available steroids testosterone or DHEA via three-step sequences. These studies feature an expedient installation of the β16-oxidation based on β14-hydroxyl-directed epoxidation and subsequent epoxide rearrangement. The following singlet oxygen oxidation of the C17 furan moiety provides access to oleandrigenin (7) in 12 steps (LLS) and a 3.1% overall yield from 8. The synthetic oleandrigenin (7) was successfully glycosylated with l-rhamnopyranoside-based donor 28 using a Pd(II)-catalyst, and the subsequent deprotection under acidic conditions provided cytotoxic natural product rhodexin B (2) in a 66% yield (two steps).

Syntheses of L‐rhamnose‐linked amino glycerolipids and their cytotoxic activities against human cancer cells

A major impediment to successful cancer treatment is the inability of clinically available drugs to kill drug‐resistant cancer cells. We recently identified metabolically stable L‐glucosaminebased glycosylated antitumor ether lipids (GAELs) that were cytotoxic to chemotherapy‐resistant cancer cells. In the absence of commercially available L‐glucosamine, many steps were needed to synthesize the compound and the overall yield was poor. To overcome this limitation, a facile synthetic procedure using commercially available L‐sugars including L‐rhamnose and L‐glucose were developed and the L‐GAELs tested for anticancer activity. The most potent analog synthesized, 3‐amino‐1‐O‐hexadecyloxy‐2R‐(O–α‐L‐rhamnopyranosyl)‐sn‐ glycerol 3, demonstrated a potent antitumor effect against human cancer cell lines derived from breast, prostate, and pancreas. The activity observed was superior to that observed with clinical anticancer agents including cisplatin and chlorambucil. Moreover, like other GAELs, 3 induced cell death by a non‐membranolytic caspase‐independent pathway.

A concise synthesis of rhamnan oligosaccharides with alternating α-(1→2)/(1→3)-linkages and repeating α-(1→3)-linkages by iterative α-glycosylation using disaccharide building blocks

A concise synthetic route to rhamnan oligosaccharides with alternating α-(1→2)/(1→3)-linkages and repeating α-(1→3)-linkages is reported. This synthesis was achieved by iterative α-glycosylation using disaccharide building blocks and through orthogonal co

InBr 3 -Catalyzed Synthesis of Aryl 1,2- trans -Thio(seleno)glycosides

InBr 3 is demonstrated to be an efficient catalyst for reactions of fully acetated aldoses with aryl mercaptans or selenophenol at room temperature, rapidly furnishing the corresponding thioglycosides or selenoglycosides with exclusively 1,2- t

Synthetic Routes toward Acidic Pentasaccharide Related to the O-Antigen of E. coli 120 Using One-Pot Sequential Glycosylation Reactions

Concise syntheses of the acidic pentasaccharide, related to the O-antigenic polysaccharide of Escherichia coli 120, as its p-methoxyphenyl glycoside, have been achieved using a one-pot sequential glycosylation technique. The glycosylations have been accom

Design, synthesis, and biological evaluation of crenatoside analogues as novel influenza neuraminidase inhibitors

Natural products, especially derived from TCMH, have been found to exert antiviral effects against influenza virus. Crenatoside, a phenylethanoid glycoside from Pogostemon cablin Benth, which has been shown as a novel effective NA inhibitor previously, is considered as the leading compound for our further SARs studies. This work presented design, synthesis of novel crenatoside analogues from readily available d-Glucose and l-rhamnose in a convergent manner. Furthermore, their biological activities and SARs were also investigated. Especially, compound 2 h showed impressive IC50 = 27.77 μg/mL against NAs, which is 3 folds more potent than the leading compound crenatoside (IC50 = 89.81 μg/mL). These results would promise their therapeutic potential for influenza disease.

Efficient one-pot per-: O -acetylation-thioglycosidation of native sugars, 4,6- O -arylidenation and one-pot 4,6- O -benzylidenation-acetylation of S -/ O -glycosides catalyzed by Mg(OTf)2

A sequential one-pot per-O-acetylation-S-/O-glycosidation of native mono and disaccharides under solvent free conditions using 0.5 mole% of Mg(OTf)2 as a non-hygroscopic, recyclable catalyst is reported. Regioselective 4,6-O-arylidenation of glycosides and thioglycosides with benzaldehyde or p-methoxybenzaldehyde dimethyl acetal is catalyzed by 10 mole% of Mg(OTf)2 to produce the corresponding 4,6-O-arylidenated product in high yields. Mg(OTf)2 can also mediate sequential one-pot benzylidenation-acetylation of mono and disaccharide based glycosides and thioglycosides in high yield.