128946-17-8

Basic information

• Product Name: Ethyl-α-D-thio-mannopyranosid
• Synonyms: Ethyl-α-D-thio-mannopyranosid
• CAS NO: 128946-17-8
• Molecular Formula: C₈H₁₆O₅S
• Molecular Weight: 224.275
• Product Categories: Carbohydrates
• Mol File: 128946-17-8.mol
• Article Data: 50

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Ethyl-α-D-thio-mannopyranosid(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl-α-D-thio-mannopyranosid(128946-17-8)
• EPA Substance Registry System: Ethyl-α-D-thio-mannopyranosid(128946-17-8)

Safety Data

• Hazardous Substances Data: 128946-17-8(Hazardous Substances Data)

Upstream product

• 32934-24-0 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 50-99-7 D-glucose 
• 75-08-1 ethanethiol 
• 32934-24-0 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-glycopyranoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 32934-24-0 S-ethyl 2,3,4,6-tetra-O-acetyl-1-deoxy-1-thio-α-D-mannopyranoside 
• 7647-01-0 hydrogenchloride 
• 4137-33-1 ethyl 1-thio-α-D-glucofuranoside 
• 604-69-3 β-D-glucose pentaacetate 
• 75-03-6 ethyl iodide 
• 83-87-4 β-D-mannopyranose pentaacetate 
• 3458-28-4 D-Mannose 
• 83-87-4 D-Mannose pentaacetate 
• 7296-15-3 alpha-D-mannopyranoside 

Downstream Products

• 32934-24-0 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 32934-24-0 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-glycopyranoside 
• 128850-48-6 ethyl 1-thio-6-O-triphenylmethyl-α-D-mannopyranoside 
• 20701-61-5 ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 20701-61-5 ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 74666-83-4 1-deoxy-1-(S-ethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 128643-87-8 ethyl 1-thio-6-O-(triphenylmethyl)-β-D-glucopyranoside 
• 105376-04-3 ethyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside 
• 151123-92-1 Ethyl 4,6-O-benzylidene-1-thio-α-D-glucopyranoside 
• 219536-50-2 ethyl 4,6-O-benzylidene-1-thio-α-D-glucopyranoside 
• 155814-72-5 (2R,3S,4S,5R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-ethylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 228699-91-0 ethyl 2,4-di-O-acetyl-3,6-di-O-trityl-1-thio-α-D-mannopyranoside 
• 39483-51-7 ethyl 2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranoside 
• 152964-72-2 ethyl 2,3-di-O-benzyl-1-thio-α-D-mannopyranoside 

Relevant articles and documents

Ring Expansion Leads to a More Potent Analogue of Ipomoeassin F

Two new ring-size-varying analogues (2 and 3) of ipomoeassin F were synthesized and evaluated. Improved cytotoxicity (IC50: from 1.8 nM) and in vitro protein translocation inhibition (IC50: 35 nM) derived from ring expansion imply that the binding pocket of Sec61α (isoform 1) can accommodate further structural modifications, likely in the fatty acid portion. Streamlined preparation of the key diol intermediate 5 enabled gram-scale production, allowing us to establish that ipomoeassin F is biologically active in vivo (MTD: μ3 mg/kg).

Enzyme-Catalyzed Regioselective Acetylation of Functionalized Glycosides

Novozym 435 (N435) is an immobilized lipase (Candida antarctica lipase B) capable of catalyzing transesterfications in organic media. This paper describes how this enzyme can be used for regioselective acetylation of unprotected carbohydrates providing protected monosaccharide building blocks in only one step. Unprotected thiogylcosides with both gluco, xylo, and manno stereochemistry were tolerated by the enzyme and afforded the acetylated products in high yields. The regioselective acetylation was easily scaled up to a 5.0 gram scale and in most cases, no purification was needed. Several other glycosides, including 2-azido-2-deoxy glucosides, galactosides, and gluconolactones, were also acetylated and the scope and limitations using N435 has been uncovered.

Beta-D-glucose short-chain fatty acid ester compound as well as preparation method and application thereof

The invention discloses a beta-D-glucose short-chain fatty acid ester compound as well as a preparation method and application thereof, and belongs to the technical field of organic synthesis. The compound is a compound shown as a formula I, or a stereoisomer, a pharmaceutically acceptable salt, a solvate or a prodrug of the compound shown as the formula I. The formula is as shown in the description, wherein R is a methyl group, an ethyl group, a propyl group, a propylene group, an isopropylidene group, a butyl group, a butylidene group, an isobutylidene group, an amyl group, a pentylidene group or an isoamylidene group. The compound has potential prevention and treatment effects on diabetes, hyperlipidemia, atherosclerosis, Alzheimer's disease, cardiovascular and cerebrovascular diseases,inflammation, tumors and depression.

Chemical glucosylation of pyridoxine

The chemical synthesis of pyridoxine-5′-β-D-glucoside (5′-β-PNG) was investigated using various glucoside donors and promoters. Hereby, the combination of α4,3-O-isopropylidene pyridoxine, glucose vested with different leaving and protecting groups and the application of stoichiometric amounts of different promoters was examined with regards to the preparation of the twofold protected PNG. Best results were obtained with 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl fluoride and boron trifluoride etherate (2.0 eq.) as promoter at 0 °C (59%). The deprotection was accomplished stepwise with potassium/sodium hydroxide in acetonitrile/water followed by acid hydrolysis with formic acid resulting in the chemical synthesis of 5′-β-PNG.