72075-06-0

Basic information

• Product Name: 2-deoxy-scyllo-inosamine
• Synonyms: 2-deoxy-scyllo-inosamine
• CAS NO: 72075-06-0
• Molecular Formula: C6H13NO4
• Molecular Weight: 0
• Mol File: 72075-06-0.mol

Chemical Properties

• Boiling Point: 301.9°C at 760 mmHg
• Flash Point: 136.4°C
• Appearance: /
• Density: 1.6g/cm³
• Vapor Pressure: 9.96E-05mmHg at 25°C
• Refractive Index: 1.658
• CAS DataBase Reference: 2-deoxy-scyllo-inosamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-deoxy-scyllo-inosamine(72075-06-0)
• EPA Substance Registry System: 2-deoxy-scyllo-inosamine(72075-06-0)

Safety Data

• Hazardous Substances Data: 72075-06-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-deoxy-scyllo-inosamine is used as a pharmaceutical compound for its potential therapeutic properties. It can be utilized in the development of drugs targeting various diseases due to its unique structure and functional groups.
Used in Chemical Synthesis:
2-deoxy-scyllo-inosamine is used as a key intermediate in the synthesis of complex organic compounds and pharmaceuticals. Its unique structure allows for the formation of new chemical entities with potential applications in various fields.
Used in Research and Development:
2-deoxy-scyllo-inosamine is used as a research compound for studying its properties and potential applications. It can be employed in academic and industrial research to explore its chemical reactivity, biological activity, and other characteristics.

InChI:InChI=1/C6H13NO4/c7-2-1-3(8)5(10)6(11)4(2)9/h2-6,8-11H,1,7H2/t2-,3+,4+,5-,6-/m0/s1

Upstream product

• 66065-95-0 1-deamino-1-epi-hydroxysisomicin 
• 66567-31-5 N-[(1S,2R,3S,4S)-2-[(2S,3R)-3-Acetylamino-6-(acetylamino-methyl)-3,4-dihydro-2H-pyran-2-yloxy]-4-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-methylamino-tetrahydro-pyran-2-yloxy)-5-ethylamino-3-hydroxy-cyclohexyl]-acetamide 
• 66065-91-6 3,2',6'-tri-N-acetyl-1-deamino-1-oxosisomicin 
• 66065-86-9 N-[(1S,2R,3R,4S)-2-[(2S,3R)-3-Acetylamino-6-(acetylamino-methyl)-3,4-dihydro-2H-pyran-2-yloxy]-5-amino-4-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-methylamino-tetrahydro-pyran-2-yloxy)-3-hydroxy-cyclohexyl]-acetamide 
• 66065-86-9 3,2',6'-tri-N-acetylsisomicin 
• 76548-06-6 (1R,2S,3S,4R,5S)-5-acetamidocyclohexane-1,2,3,4-tetrayl tetraacetate 
• 78963-40-3 2L-(2,4/3,5)-2,3,4,5-tetrahydroxycyclohexan-1-one 
• 87-89-8 D-myo-inositol 
• 4969-33-9 3-O-acetyl-5,6-dideoxy-1,2-O-isopropylidene-6-C-nitro-α-D-xylo-hex-5-enofuranose 
• 108311-24-6 2,3-dideoxy-3-nitro-D-myo-inositol-1,4,5,6-tetraacetate 
• 108392-22-9 3-acetamido-2,3-dideoxy-D-epi-inositol 
• 108311-24-6 2,3-dideoxy-3-nitro-D-epi-inositol-1,4,5,6-tetraacetate 
• 108391-64-6 3-acetamido-2,3-dideoxy-D-epi-inositol-1,4,5,6-tetraacetate 
• 1157852-12-4 5S-amino-5-deoxy-1,2:3,4-di-O-isopropylidene-(+)-proto-quercitol 

Downstream Products

• 890653-91-5 (2R,3S,4R,5S)-5-amino-2,3,4-trihydroxycyclohexanone 

Relevant articles and documents

Biosynthesis of aminoglycoside antibiotics: Cloning, expression and characterisation of an aminotransferase involved in the pathway to 2-deoxystreptamine

The gene btrR from Bacillus circulans has been cloned and expressed and shown to produce a protein which catalyses the transamination of 2-deoxy-scyllo-inosose to give 2-deoxy-scyllo-inosamine, an intermediate in the biosynthesis of 2-deoxystreptamine.

Isolation of nabscessin C from nocardia abscessus IFM 10029T and A study on biosynthetic pathway for nabscessins

A new aminocyclitol derivative, designated nabscessin C (1), was isolated from Nocardia abscessus IFM 10029T. Nabcessin C is an isomer of nabscessins A (2) and B (3) with different positioning of the acyl group. Absolute configuration of nabscessin A was determined by conversion into the 2-deoxy-scyllo-inosamine pentaacetyl derivative (4) by hydrolysis and acetylation of 2. The biosynthetic pathway of nabscessins is proposed based on gene expression analysis.

Characterization of l-glutamine:2-deoxy-scyllo-inosose aminotransferase (tbmB) from Streptomyces tenebrarius

2-Deoxystreptamine (DOS)-containing aminoglycoside-aminocyclitol (AmAc) antibiotics represent the majority of clinically important AmAcs. Biosynthetic investigations of formation of DOS in actinomycetes are limited to the characterization of 2-deoxy-scyllo-inosose synthase, the first step enzyme of the DOS biosynthetic pathway. A gene encoding l-glutamine:2-deoxy-scyllo-inosose aminotransferase (tbmB) from the tobramycin producer Streptomyces tenebrarius was expressed heterologously in Escherichia coli. The conversions of 2-deoxy-scyllo-inosose to 2-deoxy-scyllo-inosamine and scyllo-inosose to scyllo-inosamine with the activity of TbmB were determined in vitro. The results indicate that tbmB catalyzes the second step of the DOS biosynthetic pathway during the biosynthesis of 2-deoxystreptamine, a subunit of tobramycin, in S. tenebrarius.

N-arylmethylaminoquercitols, a new series of effective antidiabetic agents having α-glucosidase inhibition and antioxidant activity

Abstract A new series of N-arylalkylaminoquercitols were synthesized by reductive amination of aminoquercitol bisacetonide 5 and a variety of aryl aldehydes. The targeted N-substituted aminoquercitols having phenolic moiety (7a-7c) displayed significantly enhanced α-glucosidase inhibition, which is 26-32 times more potent than that of the unmodified aminoquercitol 6. In addition, compounds 7a-7c also retained antioxidant activity with relatively more pronounced potency than their original phenolics. This recent finding suggests an approach to develop effective antidiabetic agents by incorporating antioxidative moiety into aminocyclitol core structure.

(+)-proto-Quercitol, a natural versatile chiral building block for the synthesis of the α-glucosidase inhibitors, 5-amino-1,2,3,4-cyclohexanetetrols

An efficient synthesis of diastereomerically pure 5-amino-1,2,3,4-cyclohexanetetrols (6 and 11) and quercitol derivatives from naturally available (+)-proto-quercitol (1) is described. The stereochemistry of 1 is perfectly set up for regioselective protec

Synthesis of a new family of aminocyclitols from D-(-)-quinic acid

In continuation of our interest in the synthesis of glycosidase inhibitors, we report herein an efficient synthesis of three new polyhydroxylated amino cyclohexane derivatives (aminocyclitols) that may potentially possess important biological activities. The key step involved the highly stereoselective dihydroxylation of protected azido cyclohexene derivatives 5, 9, and 15, which were easily red from D-(-)-quinic acid. The subsequent hydrogenation step was conducted under acidic conditions to provide the target molecules in an efficient manner with high overall yields. Copyright Taylor & Francis Group, LLC.

Stereodivergent syntheses of conduramines and aminocyclitols

The diastereomers of 6-amino-cyclohex-3-ene-1,2-diols 1 (4-deoxy-3-conduramines), key building blocks for the syntheses of a large range of natural products, have been enantioselectively prepared. Diastereoselective dihydroxylation of the compounds provid

Design and synthesis of glycosidase inhibitor 5-amino-1,2,3,4- cyclohexanetetrol derivatives from (-)-vibo-quercitol

In continuation of development of bioactive inositol derivatives, a 1-O-methyl derivative of 5-amino-5-deoxy-l-talo-quercitol was designed and synthesized as an analogue of the strong α-fucosidase inhibitor, 5a-carba-α-l-fucopyranosylamine, the methyl bra

Convenient synthesis of 2-deoxy-scyllo-inosose and 2-deoxy-scyllo-inosamine: Two key intermediates on the biosynthetic pathway to aminoglycoside antibiotics

2-Deoxy-scyllo-inosose 1 and 2-deoxy-scyllo-inosamine 2 are two of the key intermediates on the biosynthetic pathway to 2-deoxystreptamine-containing aminoglycoside antibiotics. Convenient syntheses of 1, 2 and tritium-labelled 2 via stereoselective deoxy

6-Exo Free Radical Cyclization of Acyclic Carbohydrate Intermediates: A New Synthetic Route to Enantiomerically Pure Polyhydroxylated Cyclohexane Derivatives

The 6-exo free radical cyclization of conveniently functionalized acyclic carbohydrate derivatives is a new and efficient method for the asymmetric synthesis of polyhydroxylated cyclohexane compounds (aminocyclitols, pseudosugars).The scope and versatilit