117821-07-5

Basic information

• Product Name: (2S,3S,4S,5S)-2-(hydroxymethyl)piperidine-3,4,5-triol
• Synonyms: 3,4,5-piperidinetriol, 2-(hydroxymethyl)-, (2S,3S,4S,5S)-
• CAS NO: 117821-07-5
• Molecular Formula: C₆H₁₃NO₄
• Molecular Weight: 163.1717
• Mol File: 117821-07-5.mol
• Article Data: 45

Chemical Properties

• Boiling Point: 361.1°C at 760 mmHg
• Flash Point: 197.3°C
• Density: 1.456g/cm³
• Vapor Pressure: 1.13E-06mmHg at 25°C
• Refractive Index: 1.582
• CAS DataBase Reference: (2S,3S,4S,5S)-2-(hydroxymethyl)piperidine-3,4,5-triol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S,4S,5S)-2-(hydroxymethyl)piperidine-3,4,5-triol(117821-07-5)
• EPA Substance Registry System: (2S,3S,4S,5S)-2-(hydroxymethyl)piperidine-3,4,5-triol(117821-07-5)

Safety Data

• Hazardous Substances Data: 117821-07-5(Hazardous Substances Data)

Usage

General Description

The chemical compound (2S,3S,4S,5S)-2-(hydroxymethyl)piperidine-3,4,5-triol, also known as D-Sorbose, is a sugar alcohol that is commonly found in fruits and vegetables. It is a stereoisomer of D-tagatose and is used as a sweetener in various food products. D-Sorbose has antioxidant properties and has been studied for its potential health benefits, including its ability to improve insulin sensitivity and regulate blood sugar levels. It is also being investigated for its potential role in cancer prevention and treatment. D-Sorbose has been found to have low toxicity and is generally recognized as safe for consumption.

Upstream product

• 121195-27-5 2,4-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-mannitol 
• 91364-19-1 5-amino-1-O-benzyl-5-deoxy-2,3-O-isopropylidene-α-D-mannofuranose 
• 160226-26-6 (2R,3R,4R,5R)-1,4-dideoxy-1,6-imino-3,4-O-isopropylidene-D-mannitol 
• 18006-23-0 3,6-Di-O-benzyl-1,2-O-isopropylidene-β-L-ido-furanose 
• 40984-16-5 6,6'-dichloro-6,6'-didesoxysaccharose 
• 33585-16-9 6,6'-diazido-6,6'-dideoxysucrose 
• 22529-61-9 (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 
• 226884-09-9 methyl 2,6-dideoxy-2,6-imino-D-mannonate 
• 1112338-13-2 (3R,4R,5R)-3,4,5-tris(benzyloxy)-6-benzyloxymethyl-2,3,4,5-tetrahydropyridine 1-oxide 
• 1112338-38-1 (2R,3R,4R,5R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)piperidine 
• 160147-90-0 (2S,3R,4R,5R)-methyl 2,6-dideoxy-2,6-imino-3,4-O-isopropylidene-D-mannonate 
• 151428-17-0 methyl 2,3-O-isopropylidene-α-D-lyxo-hexofuranosid-5-ulose 
• 27954-10-5 methyl 2,3-O-isopropylidene-α-D-mannofuranoside 
• 176209-07-7 1-(2-Furyl)-2-methoxy-N-tosylethylamine 

Downstream Products

• 679404-77-4 N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-mannitol 
• 155501-85-2 N-butyl-1-deoxygalactonojirimycin 
• 223771-83-3 N-nonyl 1-deoxymannojirimycin 
• 216758-20-2 (2R,3R,4R,5R)-1-(5-(((3R,5R,7R)-adamantan-1-yl)methoxy)pentyl)-2-(hydroxymethyl)piperidine-3,4,5-triol 
• 679404-78-5 2,6-di-O-pivaloyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-mannitol 
• 117821-08-6 1,5-dideoxy-1,5-(methyliminiumyl)-D-mannitol 

Relevant articles and documents

Asymmetric total syntheses of (+)-2,5-dideoxy-2,5-imino-D-glucitol [(+)-DGDP] and (?)-1-deoxymannojirimycin [(?)-DMJ] via an extended chiral 1,3-oxazine

The asymmetric total syntheses of (+)-2,5-dideoxy-2,5-imino-D-glucitol [(+)-DGDP] 1 and (?)-1-deoxymannojirimycin [(?)-DMJ] 2 were achieved using an extended chiral 1,3-oxazine. The key synthetic strategies included extension of the chirality of anti,syn-oxazine 3 using diastereoselective dihydroxylation, and piperidine and pyrrolidine ring formation. Starting from readily available anti,syn-oxazine 3, (+)-DGDP 1 was synthesized in 5 steps with 31.6% overall yield and (?)-DMJ 2 was synthesized in 4 steps with 60.6% overall yield.

Transforming flask reaction into cell-based synthesis: Production of polyhydroxylated molecules via engineered Escherichia coli

Dihydroxyacetone phosphate (DHAP)-dependent aldolases have been intensively studied and widely used in the synthesis of carbohydrates and complex polyhydroxylated molecules. However, strict specificity toward donor substrate DHAP greatly hampers their synthetic utility. Here, we transformed DHAP-dependent aldolases-mediated by in vitro reactions into bioengineered Escherichia coli (E. coli). Such flask-to-cell transformation addressed several key issues plaguing in vitro enzymatic synthesis: (1) it solves the problem of DHAP availability by in vivo-hijacking DHAP from the glycolysis pathway of the bacterial system, (2) it circumvents purification of recombinant aldolases and phosphatase, and (3) it dephosphorylates the resultant aldol adducts in vivo, thus eliminating the additional step for phosphate removal and achieving in vivo phosphate recycling. The engineered E. coli strains tolerate a wide variety of aldehydes as acceptor and provide a set of biologically relevant polyhydroxylated molecules in gram scale.

Asymmetric synthesis of 1-deoxyazasugars from chiral aziridines

A general and facile synthesis of enantiopure 1-deoxyazasugars was achieved from stereoselective dihydroxylation of a common synthetic intermediate, piperidine ring fused oxazolidin-2-one, originating from a commercially available starting substrate, chiral aziridine-2-carboxylate, in high yields. The Royal Society of Chemistry 2011.