17087-84-2

Basic information

• Product Name: 2,3:5,6-DI-O-ISOPROPYLIDENE-A-D-MANNO-FU RANOSYL CHLORIDE
• Synonyms: 2,3:5,6-DI-O-ISOPROPYLIDENE-A-D-MANNO-FU RANOSYL CHLORIDE;2,3:5,6-di-O-isopropylidene-A-D-*mannofuranosyl C;2,3:5,6-DI-O-ISOPROPYLIDENE-A-D-*MANNOFU RANOSYL CHL;1-Chloro-2,3:5,6-diisopropylidene-D-mannoside;2,3:5,6-di-O-isopropylidene-alpha-D-mannofuranosyl Cl;2,3:5,6-Di-O-isopropylidene-α-D-mannofuranosyl chloride
• CAS NO: 17087-84-2
• Molecular Formula: C₁₂H₁₉ClO₅
• Molecular Weight: 278.73
• Mol File: 17087-84-2.mol
• Article Data: 25

Chemical Properties

• Appearance: /
• Storage Temp.: ?20°C
• CAS DataBase Reference: 2,3:5,6-DI-O-ISOPROPYLIDENE-A-D-MANNO-FU RANOSYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3:5,6-DI-O-ISOPROPYLIDENE-A-D-MANNO-FU RANOSYL CHLORIDE(17087-84-2)
• EPA Substance Registry System: 2,3:5,6-DI-O-ISOPROPYLIDENE-A-D-MANNO-FU RANOSYL CHLORIDE(17087-84-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-26
• Hazardous Substances Data: 17087-84-2(Hazardous Substances Data)

Usage

Molecular weight

447.25 g/mol

Appearance

White solid

Solubility

Soluble in organic solvents such as pyridine, DMSO, and DMF

Functional groups

Isopropylidene group, furanosyl ring, and chloride group

Derivative of α-D-mannose

A sugar molecule commonly found in nature

Use in organic synthesis

Protects hydroxyl groups

Building block in carbohydrate chemistry

Used in the synthesis of complex carbohydrate derivatives and glycoconjugates

Selective manipulation

The isopropylidene group allows for selective manipulation of other parts of the molecule

Versatile chemical reagent

Used in the production of various complex carbohydrate compounds.

Upstream product

• 141561-24-2 (2,3:5,6-Di-O-isopropyliden-β-D-mannofuranosyl)-methyl-disulfid 
• 62-53-3 aniline 
• 7757-38-2 (3aS,6R,6aS)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ol 
• 357604-61-6 2,3:4,6-di-O-isopropylidene-D-mannopyranose 
• 3458-28-4 D-Mannose 
• 530-26-7 D-Mannose 
• 14131-84-1 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 
• 882-33-7 diphenyldisulfane 
• 7757-38-2 2,3,5,6-di-O-isopropylidene-D-mannofuranose 
• 7757-38-2 O²,O³,O⁵,O⁶-diisopropylidene D-mannofuranose 
• 7757-38-2 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 

Downstream Products

• 1186034-75-2 1,4-anhydro-5,6-O-isopropylidene-2-deoxy-1-C-phenyl-D-arabino-hex-1-enitol 
• 857897-76-8 1-azido-1-deoxy-2,3-O-isopropylidene-6-O-p-toluenesulfonyl-β-D-mannofuranose 
• 505081-54-9 (2R,3R,7S,7aS)-3-hydroxy-7-methyl-2-((E)-prop-1-en-1-yl)-2,3,7,7a-tetrahydro-5H-furo[3,4-b]pyran-5-one 

Relevant articles and documents

Highly regioselective and stereoselective synthesis of C-Aryl glycosidesvianickel-catalyzedortho-C-H glycosylation of 8-aminoquinoline benzamides

C-Aryl glycosides are of high value as drug candidates. Here a novel and cost-effective nickel catalyzedortho-CAr-H glycosylation reaction with high regioselectivity and excellent α-selectivity is described. This method shows great functional group compatibility with various glycosides, showing its synthetic potential. Mechanistic studies indicate that C-H activation could be the rate-determining step.

Synthesis of Bioactive Side-Chain Analogues of TAN-2483B

The fungal metabolite TAN-2483B has a 2,6-trans-relationship across the pyran ring of its furo[3,4-b]pyran-5-one core, which has thwarted previous attempts at its synthesis. We have now developed a chiral pool approach to this core and prepared side-chain

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.