14199-88-3

Basic information

• Product Name: 1-DEOXY-1-NITRO-D-SORBITOL
• Synonyms: 1-DEOXY-1-NITRO-D-SORBITOL;1-deoxy-1-nitro-D-glucitol;1-Nitro-1-deoxy-D-glucitol;Einecs 238-052-3
• CAS NO: 14199-88-3
• Molecular Formula: C₆H₁₃NO₇
• Molecular Weight: 211.17
• EINECS: 238-052-3
• Product Categories: Carbohydrates;Carbohydrates A to;Carbohydrates D-FBiochemicals and Reagents;Monosaccharide
• Mol File: 14199-88-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 608.3°Cat760mmHg
• Flash Point: 268.9°C
• Appearance: /
• Density: 1.632g/cm³
• Vapor Pressure: 2.45E-17mmHg at 25°C
• Refractive Index: 1.585
• CAS DataBase Reference: 1-DEOXY-1-NITRO-D-SORBITOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1-DEOXY-1-NITRO-D-SORBITOL(14199-88-3)
• EPA Substance Registry System: 1-DEOXY-1-NITRO-D-SORBITOL(14199-88-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 14199-88-3(Hazardous Substances Data)

Usage

Chemical structure

1-Deoxy-1-nitro-D-sorbitol is a nitro sugar alcohol.

Synthesis

It is used in the synthesis of nitrosugar derivatives.

Potential applications

It has potential as a pharmaceutical intermediate, a nitric oxide releasing molecule, an antibacterial agent, an antitumor agent, a vasodilator, and an anti-inflammatory agent.

Versatility

It has a range of potential applications in various fields, including medicine and biotechnology.

InChI:InChI=1/C6H13NO7/c8-2-4(10)6(12)5(11)3(9)1-7(13)14/h3-6,8-12H,1-2H2/t3-,4+,5+,6+/m0/s1

Upstream product

• 75-52-5 nitromethane 
• 532-20-7 L-arabinose 
• 10323-20-3 D-Arabinose 
• 124-41-4 sodium methylate 

Downstream Products

• 488-43-7 1-Amino-1-deoxy-D-glucitol 
• 50-99-7 D-glucose 
• 5735-25-1 1-Acetamido-1-deoxy-D-glucit 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-L-glucofuranose 

Relevant articles and documents

Extension of chains of 1-deoxy-1-nitroalditols by nitrile oxide cycloaddition. Synthesis of 4-N-substituted 3,4-didesoxy-2-ulosonic acids

Treatment of protected nitroalditols 1a or 2 with silylenolpyruvate (3) or methyl acrylate leads via nitrile oxide cycloadditon to cyclo-tautomers of oximes, 5 or 4, respectively 4,5-dihydro-isoxazole 6. N-Acetyl-4-deoxy-4- (E/Z)-hydroxyimino-neuraminic acid (7) is obtained by deprotection of 4. Hydrogenation of 7 yields N-acetyl-4-amino-4-deoxy-neuraminic acid (9) and pentahydroxy-nononic acids 12a,b. The synthesis is useful for the chain extension of protected nitroalditols 13a and 20a, to give the corresponding oximes 15 and 22. This work provides a general method for the extension of sugar chains by three C-atoms and thus a novel synthesis of α-keto acids containing an oxime and amino function.

Synthesis of daunosamine

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