14257-40-0

Basic information

• Product Name: 6-CHLORO-6-DEOXY-D-MANNOSE
• Synonyms: 2,3,4,6-Tetra-O-acetyl-a-D-mannopyranosylchloride;Chloro 2,3,4,6-Tetra-O-acetyl-α-D-mannopyranoside;2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyl chloride;2,3,4,6-Tetra-O-acetyl-a-D-mannopyranosyl chloride ,96%;Acetochloro-alpha-D-mannose, (2R,3R,4S,5S,6R)-2-(Acetoxymethyl)-6-chlorotetrahydro-2H-pyran-3,4,5-triyl triacetate;α-D-Mannopyranosyl Chloride, 2,3,4,6-Tetraacetate;6-CHLORO-6-DEOXY-D-MANNOSE;ACETOCHLORO-ALPHA-D-MANNOSE
• CAS NO: 14257-40-0
• Molecular Formula: C₁₄H₁₉ClO₉
• Molecular Weight: 366.75
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 14257-40-0.mol
• Article Data: 31

Chemical Properties

• Melting Point: 69-71°C
• Boiling Point: 406.4 °C at 760 mmHg
• Flash Point: 144.2 °C
• Appearance: white crystalline solid
• Density: 1.33 g/cm³
• Vapor Pressure: 8.15E-07mmHg at 25°C
• Refractive Index: 1.486
• Storage Temp.: Store below -20C
• Solubility: Chloroform, Ether
• Stability: Store in Freezer, Stabilized with 2% Calcium Carbonate
• CAS DataBase Reference: 6-CHLORO-6-DEOXY-D-MANNOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CHLORO-6-DEOXY-D-MANNOSE(14257-40-0)
• EPA Substance Registry System: 6-CHLORO-6-DEOXY-D-MANNOSE(14257-40-0)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 14257-40-0(Hazardous Substances Data)

Usage

Description

6-CHLORO-6-DEOXY-D-MANNOSE, also known as Chloro 2,3,4,6-Tetra-O-acetyl-α-D-mannopyranoside, is a mannose derivative. D-Mannose is a carbohydrate that plays a crucial role in the glycosylation of molecules in various cellular processes. 6-CHLORO-6-DEOXY-D-MANNOSE is characterized by its white crystalline solid appearance.

Uses

Used in Pharmaceutical Industry:
6-CHLORO-6-DEOXY-D-MANNOSE is used as an intermediate in the synthesis of various pharmaceutical compounds for its ability to be modified and incorporated into complex molecules.
Used in Biochemical Research:
6-CHLORO-6-DEOXY-D-MANNOSE is used as a research tool for studying the role of mannose in cellular processes and glycosylation, aiding in the understanding of its biological functions and potential therapeutic applications.
Used in Drug Development:
6-CHLORO-6-DEOXY-D-MANNOSE is used as a building block in the development of new drugs targeting glycosylation-related pathways, which may have implications in the treatment of various diseases.
Used in Diagnostic Applications:
6-CHLORO-6-DEOXY-D-MANNOSE can be used in the development of diagnostic tools and assays that rely on the specific recognition of mannose-containing molecules, potentially aiding in the detection and monitoring of certain conditions.
Used in Material Science:
6-CHLORO-6-DEOXY-D-MANNOSE may be utilized in the creation of novel materials with unique properties, such as those with enhanced biocompatibility or specific binding capabilities, due to its carbohydrate nature.
Used in Food Industry:
6-CHLORO-6-DEOXY-D-MANNOSE could potentially be used in the development of new additives or ingredients for the food industry, leveraging its properties to enhance the texture, flavor, or nutritional content of products.

InChI:InChI=1/C14H19ClO9/c1-6(16)20-5-10-11(21-7(2)17)12(22-8(3)18)13(14(15)24-10)23-9(4)19/h10-14H,5H2,1-4H3/t10-,11-,12-,13-,14-/m0/s1

Upstream product

• 530-26-7 D-Mannose 
• 75-36-5 acetyl chloride 
• 3458-28-4 D-Mannose 
• 25878-60-8 D-galactose pentaacetate 
• 36868-85-6 4-chlorophenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose 
• 6763-46-8 2,3,4,5,6-Penta-O-acetyl-D-galaktose 
• 439-03-2 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl fluoride 
• 4163-60-4 β-D-galactose peracetate 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 26189-59-3 1-chloro-1-(dimethylamino)-2-methyl-1-propene 
• 83-87-4 D-Mannose pentaacetate 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 

Downstream Products

• 57884-82-9 2,3,4,6-tetra-O-acetyl-β-D-mannopyranose 
• 22860-22-6 2,3,4,6-tetra-O-acetyl-α-D-mannopyranose 
• 14227-87-3 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl chloride 
• 51295-66-0 2,3,6-Tri-O-acetyl-2-O-(trichloroacetyl)-β-D-galactopyranosyl chloride 
• 1290116-45-8 C₂₅H₃₅N₇O₁₀ 
• 65864-60-0 2,3,4,6-tetra-O-acetyl-1-azido-1-deoxy-β-D-mannopyranose 
• 1210451-90-3 N-(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)methanesulfonamide 
• 41355-50-4 1-amino-2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl 
• 3682-06-2 (2R,3R,4R,5R,6R)-2-(acetoxymethyl)-6-phenyltetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 2873-29-2 D-glucal triacetate 
• 176692-28-7 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzoyl-4-S-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-4-thio-β-D-galactopyranoside 
• 94427-00-6 azido-2,3,4,6-tetra-O-acetyl-1-deoxy-α-D-galactopyranose 

Relevant articles and documents

Stereoselective Preparation of C-Aryl Glycosides via Visible-Light-Induced Nickel-Catalyzed Reductive Cross-Coupling of Glycosyl Chlorides and Aryl Bromides

A nickel-catalyzed cross-coupling reaction of glycosyl chlorides with aryl bromides has been developed. The reaction proceeds smoothly under visible-light irradiation and features the use of bench-stable glycosyl chlorides, allowing the highly stereoselective synthesis of C-aryl glycosides. (Figure presented.).

Nonenzymatic synthesis of anomerically pure, mannosylbased molecular probes for scramblase identification studies

The chemical synthesis of molecular probes to identify and study membrane proteins involved in the biological pathway of protein glycosylation is described. Two short-chain glycolipid analogs that mimic the naturally occurring substrate mannosyl phosphoryl dolichol exhibit either photoreactive and clickable properties or allow the use of a fluorescence readout. Both probes consist of a hydrophilic mannose headgroup that is linked to a citronellol derivative via a phosphodiester bridge. Moreover, a novel phosphoramidite chemistry-based method offers a straightforward approach for the non-enzymatic incorporation of the saccharide moiety in an anomerically pure form.

Efficient Synthesis of α-Glycosyl Chlorides Using 2-Chloro-1,3-dimethylimidazolinium Chloride: A Convenient Protocol for Quick One-Pot Glycosylation

A mild and convenient method for the synthesis of α-glycosyl chlorides in high 80–96 % yields within 15–30 min using 2-chloro-1,3-dimethylimidazolinium chloride (DMC) is disclosed. The method has a wide substrate scope and is compatible with labile OH protecting groups, including benzyl, acetyl, benzoyl, isopropylidene, benzylidene, TBDMS (tert-butyldimethylsilyl), and TBDPS (tert-butyldiphenylsilyl) groups. The excellent α selectivity obtained in this reaction is attributed to in-situ isomerization of β-glycosyl chlorides to the more stable α-glycosyl chlorides, as demonstrated by 1H NMR spectroscopic studies. Disarmed sugars with OBz or OAc groups at C-2 were chlorinated at a faster rate but ismomerized (β→α) at a slower rate than armed sugars with an OBn group at C-2. More importantly, the method enables highly desirable one-pot glycosylation reactions to take place, thus allowing efficient syntheses of disaccharides and simple O-glycosylated sugars in high overall yields without the need for separation or purification of the α-glycosyl chloride donors. This method will be especially useful for direct glycosylation reactions using glycosyl chloride donors that are unstable upon separation and purification.