18545-96-5

Basic information

• Product Name: 1-Deoxy-D-glucitol
• Synonyms: 1-Deoxy-D-glucitol;1-Deoxyglucitol
• CAS NO: 18545-96-5
• Molecular Formula: C6H14O5
• Molecular Weight: 166.17
• Mol File: 18545-96-5.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Deoxy-D-glucitol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Deoxy-D-glucitol(18545-96-5)
• EPA Substance Registry System: 1-Deoxy-D-glucitol(18545-96-5)

Safety Data

• Hazardous Substances Data: 18545-96-5(Hazardous Substances Data)

Usage

General Description

1-Deoxy-D-glucitol, also known as Fagomine, is a naturally occurring sugar alcohol found in certain fruits and vegetables. It is a derivative of glucose and is similar in structure to sorbitol. 1-Deoxy-D-glucitol has been studied for its potential health benefits, including its ability to lower blood sugar levels and improve insulin sensitivity. It has also been investigated for its anti-inflammatory and antibacterial properties. Additionally, 1-Deoxy-D-glucitol is used as a sugar substitute in some food products and as a sweetener in pharmaceuticals and dietary supplements. Overall, 1-Deoxy-D-glucitol has shown promise as a potential therapeutic agent for managing diabetes and related complications.

Upstream product

• 7333-29-1 1-deoxy-D-glucitol penta-acetate 
• 1941-52-2 D-glucose diethyl dithioacetal 
• 2438-80-4 L-Fucose 
• 488-28-8 hexane-1,2,3,4,5-pentaol 
• 13074-06-1 L-fucitol 
• 1941-52-2 D-glucose diethyl mercaptal 
• 1109-15-5 tris(pentafluorophenyl)borate 
• 29217-83-2 6-deoxy-L-gulono-1,4-lactone 
• 149056-73-5 (S)-1-[(4R,4'R,5'R)-2,2,2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl]ethanol 
• 94284-20-5 1-deoxy-3,4:5,6-di-O-isopropylidene-D-arabino-hex-2-ulose 
• 4435-02-3 3,4:5,6-di-O-isopropylidene-D-glucose diethyl dithioacetal 
• 50-99-7 D-glucose 
• 84985-25-1 6-deoxy-L-mannose 
• 3615-37-0 D-Fucose 

Downstream Products

• 488-28-8 racemic rhodeitol 
• 123594-91-2 Anthracene-9-carboxylic acid (2R,3R,4R,5S)-2,3,4,5-tetrakis-[(E)-3-(4-methoxy-phenyl)-acryloyloxy]-hexyl ester 

Relevant articles and documents

New and Efficient Synthesis of 6-Deoxy-L-gulose

An efficient synthetic procedure for the transformation of D-glucurono-γ-lactone to 6-deoxy-L-gulose (20) in five steps and 52 percent yield is described.The scheme relies on the selective blocking of the 2-(silyl ether) and 3,5-(isopropylidene) hydroxyl groups and then diisobutylaluminum hydride reduction of the lactone carbonyl.An alternate route that relies on the more standard sodium amalgam reduction of the lactone triol was found to be technically inefficient and to result in a poor overall yield.

Modulating Electrostatic Interactions in Ion Pair Intermediates To Alter Site Selectivity in the C?O Deoxygenation of Sugars

Controlling which products one can access from the predefined biomass-derived sugars is challenging. Changing from CH2Cl2 to the greener alternative toluene alters which C?O bonds in a sugar are cleaved by the tris(pentafluorophenyl)borane/HSiR3 catalyst system. This increases the diversity of high-value products that can be obtained through one-step, high-yielding, catalytic transformations of the mono-, di-, and oligosaccharides. Computational methods helped identify this non-intuitive outcome in low dielectric solvents to non-isotropic electrostatic enhancements in the key ion pair intermediates, which influence the reaction coordinate in the reactivity-/selectivity-determining step. Molecular-level models for these effects have far-reaching consequences in stereoselective ion pair catalysis.

HYDRAZINOLYSIS OF MONOSACCHARIDES: A TWO-STEP SYNTHESIS OF CHIRAL PENTANE-1,2,3-TRIOLS FROM PENTOSES AND OBSERVATIONS ON THE HYDRAZINOLYSIS OF GLYCOPROTEINS AND GLYCOPEPTIDES

1,2-Dideoxyalditols, the corresponding 1-alkenes, and 1-deoxyalditols are formed in various proportions from D-glucose, D-mannose, L-arabinose, and D-xylose by the action of refluxing hydrazine.Sequential hydrazinolysis, catalytic hydrogenation, and chromatography afford a route to 1,2-dideoxyalditols.For example, 1,2-dideoxy-L-erythro-pentitol is formed from L-arabinose in 42percent yield, and D-xylose is a source of 1,2-dideoxy-D-threo-pentitol (50percent).Under the conditions (anhydrous hydrazine at 100 deg C for 30 h in the absence of air) used Montreuil for the hydrazinolysis of glycoproteins and glycopeptides, no 1,2-dideoxialditol was formed; degradation was incomplete, there being some aldose hydrazone present.Under Kochetkov's hydrazinolysis conditions (105 deg C for 10 h with hydrazinium sulphate), less degradation occured and product from D-galactose was identified as 1-deoxy-D-tagatose hydrazone.