1020538-15-1

Basic information

• Product Name: prop-2-ynyl-β-D-mannopyranoside
• Synonyms: prop-2-ynyl-β-D-mannopyranoside
• CAS NO: 1020538-15-1
• Molecular Weight: 218.207
• Mol File: 1020538-15-1.mol

Chemical Properties

• CAS DataBase Reference: prop-2-ynyl-β-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: prop-2-ynyl-β-D-mannopyranoside(1020538-15-1)
• EPA Substance Registry System: prop-2-ynyl-β-D-mannopyranoside(1020538-15-1)

Safety Data

• Hazardous Substances Data: 1020538-15-1(Hazardous Substances Data)

Upstream product

• 3458-28-4 D-Mannose 
• 107-19-7 propargyl alcohol 
• 530-26-7 D-Mannose 
• 106-96-7 propargyl bromide 
• 83-87-4 D-Mannose pentaacetate 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 2936-70-1 (2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 

Relevant articles and documents

Mannosylated Poly(ethylene imine) Copolymers Enhance saRNA Uptake and Expression in Human Skin Explants

Messenger RNA (mRNA) is a promising platform for both vaccines and therapeutics, and self-amplifying RNA (saRNA) is particularly advantageous, as it enables higher protein expression and dose minimization. Here, we present a delivery platform for targeted delivery of saRNA using mannosylated poly(ethylene imine) (PEI) enabled by the host-guest interaction between cyclodextrin and adamantane. We show that the host-guest complexation does not interfere with the electrostatic interaction with saRNA and observed that increasing the degree of mannosylation inhibited transfection efficiency in vitro, but enhanced the number of cells expressing GFP by 8-fold in human skin explants. Besides, increasing the ratio of glycopolymer to saRNA also enhanced the percentage of transfected cells ex vivo. We identified that these mannosylated PEIs specifically increased protein expression in the epithelial cells resident in human skin in a mannose-dependent manner. This platform is promising for further study of glycosylation of PEI and targeted saRNA delivery.

Sequential acid-catalyzed alkyl glycosylation and oligomerization of unprotected carbohydrates

An efficient method has been developed to synthesize end-functionalized oligosaccharides from unprotected monosaccharides in a one-pot/two-step approach. In the first step, mannose (and glucose) was functionalized with an alkyne group at the anomeric position through the Fisher-glycosylation reaction with propargyl alcohol as a glycosyl acceptor. In the second step, the functionalized monosaccharides were oligomerized and the experimental conditions were optimized by varying the temperature, time and the molar ratio between alcohol and sugar to reach a up to 8. The obtained oligosaccharides showed complete propargylation at their reducing chain-end and were successfully coupled to oleic acidviathe Huisgen reaction, affording bio-based surfactants.

Selectivity of 1-O-Propargyl-D-Mannose Preparations

Thanks to their ability to bind to specific biological receptors, mannosylated structures are examined in biomedical applications. One of the most common ways of linking a functional moiety to a structure is to use an azide-alkyne click reaction. Therefore, it is necessary to prepare and isolate a propargylated mannose derivative of high purity to maintain its bioactivity. Three known preparations of propargyl-α-mannopyranoside were revisited, and products were analysed by NMR spectroscopy. The preparations were shown to yield by-products that have not been described in the literature yet. Our experiments showed that one-step procedures could not provide pure propargyl-α-mannopyranoside, while a three-step procedure yielded the desired compound of high purity.

Anomeric alkylations and acylations of unprotected mono- and disaccharides mediated by pyridoneimine in aqueous solutions

A site-specific deprotonation followed by alkylations and acylations of sugar hemiacetals to the corresponding alkyl glycosides and acylated sugars in aqueous solutions is disclosed herein. Pyridoneimine as a new base is developed to mediate the deprotonation of readily available sugar hemiacetals and further reactions with alkylation and acylation agents.

1,2-cis Alkyl glycosides: Straightforward glycosylation from unprotected 1-thioglycosyl donors

A 1,2-cis-alkyl glycosidation protocol that makes use of unprotected phenyl 1-thioglycosyl donors is reported. Glycosylation of various functionalized alcohols was accomplished in moderate to high yield and selectivity to give the 1,2-cis-glycosides. In order to quickly develop optimum glycosylation conditions, an FIA (flow injection analysis)-ESI-TOF-MS method was developed that enabled rapid and quantitative evaluation of yield on small scale. This methodology, coupled with NMR spectroscopy, allowed for rapid evaluation of the overall reactions.