96613-89-7

Basic information

• Product Name: 1-DEOXY-1-NITRO-D-IDITOL HEMIHYDRATE
• Synonyms: 1-DEOXY-1-NITRO-D-IDITOL HEMIHYDRATE
• CAS NO: 96613-89-7
• Molecular Formula: C₆H₁₃NO₇
• Molecular Weight: 229.19
• Product Categories: Carbohydrate Synthesis;Monosaccharides;Specialty Synthesis
• Mol File: 96613-89-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: 88 °C(lit.)
• Appearance: /
• CAS DataBase Reference: 1-DEOXY-1-NITRO-D-IDITOL HEMIHYDRATE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-DEOXY-1-NITRO-D-IDITOL HEMIHYDRATE(96613-89-7)
• EPA Substance Registry System: 1-DEOXY-1-NITRO-D-IDITOL HEMIHYDRATE(96613-89-7)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 96613-89-7(Hazardous Substances Data)

Usage

Common Use

Organic synthesis and as a reagent in chemical reactions

Derivative of

Inositol

Starting Material

Synthesis of various pharmaceuticals and organic compounds

Structure

Unique nitro sugar structure

Application

Development of new drugs and bioactive molecules

Physical State

Crystalline solid

Stability

Stable under normal conditions

Handling

Easily handled and stored

Upstream product

• 58-86-6 D-xylose 
• 75-52-5 nitromethane 
• 532-20-7 L-arabinose 

Downstream Products

• 5978-95-0 D-idose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-L-glucofuranose 

Relevant articles and documents

Direct conversion of 1-deoxy-1-nitroalditols to methyl glycofuranosides

Treatment of the sodium nitronate forms of 1-deoxy-1-nitrohexitols with methanolic sulfuric or hydrochloric acid at -30 °C leads to their regiospecific conversion to the corresponding methyl glycofuranosides. The reaction exhibits more pronounced stereoselectivity for 1-deoxy-1-nitroalditols with the 2,3-erythro configuration than with the 2,3-threo substrates and cis methyl glycofuranosides are the major products. The observed stereoselectivity indicates the lysis of the protonated aci-nitro form which is a two-step process consisting of nucleophilic addition to the protonated carbon-nitrogen double bond followed by the bimolecular nucleophilic substitution of the nitrogen-containing residue.

Addition of Nitromethane to Aldoses. - A Comprehensive Study of the Diastereoselectivity of the Fischer-Sowden Reaction by Help of 13C-NMR Spectroscopy

The addition of nitromethane to aldoses, commonly referred to as "Fischer-Sowden reaction", is not as stereoselective as can be concluded from the literature.This is the outcome of a comprehensive study which covered besides glyceraldehyde all aldotetroses, -pentoses and -hexoses.The ratio of the pair of diastereomeric nitroalditols has been determined in each case by 13C-NMR spectroscopy.Thus, incidentially, a whole set of spectral data for all tetritols, pentitols, hexitols and heptitols with a terminal nitro group has been obtained, which can be correlated systematically to the respective data for the parent alditols.From these results follows that at least under conditions which give high yields of products, the reaction is thermodynamically controlled; thus, the product ratio is determined by the different energy content of the product nitroalditols (or their nitronates), which is a result of different patterns of steric interactions between substituents.