14187-81-6

Basic information

• Product Name: (1α,2β,3α,4β,6β)-4,6-Diamino-1,2,3-cyclohexantriol
• Synonyms: (1α,2β,3α,4β,6β)-4,6-Diamino-1,2,3-cyclohexantriol
• CAS NO: 14187-81-6
• Molecular Weight: 246.263
• Mol File: 14187-81-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (1α,2β,3α,4β,6β)-4,6-Diamino-1,2,3-cyclohexantriol(CAS DataBase Reference)
• NIST Chemistry Reference: (1α,2β,3α,4β,6β)-4,6-Diamino-1,2,3-cyclohexantriol(14187-81-6)
• EPA Substance Registry System: (1α,2β,3α,4β,6β)-4,6-Diamino-1,2,3-cyclohexantriol(14187-81-6)

Safety Data

• Hazardous Substances Data: 14187-81-6(Hazardous Substances Data)

Upstream product

• 42756-57-0 methyl 2-acetamido-2-deoxy-6-O-trityl-D-glucopyranoside 
• 20183-98-6 N,N'-Diacetyl-all-cis-1,3-diamino-4,5,6-trihydroxy-cyclohexan 
• 110085-90-0 1,2-dideoxy-4,5;6,7-di-O-isopropylidene-3-O-methylsulfonyl-1-nitro-D-manno-heptitol 
• 112929-32-5 1L-(1,2,4/3,5)-2,3-O-isopropylidene-1-O-(methylsulfonyl)-5-nitro-1,2,3,4-cyclohexanetetrol 
• 112929-33-6 1L-(1,2,4/3,5)-1-O-(methylsulfonyl)-5-nitro-1,2,3,4-cyclohexanetetrol 
• 112952-02-0 1,2-dideoxy-4,5;6,7-di-O-isopropylidene-1-nitro-3-O-(trifluoromethylsulfonyl)-D-manno-heptitol 
• 112929-30-3 1,2-dideoxy-4,5-O-isopropylidene-3-O-methylsulfonyl-1-nitro-D-manno-heptitol 
• 112929-31-4 5,6-dideoxy-3,4-O-isopropylidene-4-O-methylsulfonyl-6-nitro-al-D-arabino-hexose 
• 112929-29-0 1,2-dideoxy-4,5;6,7-di-O-isopropylidene-1-nitro-D-manno-heptitol 
• 112929-37-0 (4S,5R)-5-((S)-1-Azido-3-nitro-propyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde 
• 35988-91-1 1,2-dideoxy-1-nitro-D-manno-heptitol 
• 62774-78-1 (1α,2α,6α)-2-(2,4-Dinitrophenoxy)-7-oxabicyclo<4.1.0>hept-3-en 
• 62774-79-2 (1α,2α,3α,5α,7α)-2-(2,4-Dinitrophenoxy)-4,8-dioxatricyclo<5.1.0.0^3,5>octan 
• 55990-88-0 (1α,2α,3α,5α,7α)-4,8-Dioxatricyclo<5.1.0.0^3,5>octan-2-ol-acetat 

Downstream Products

• 6216-31-5 2-deoxystreptamine pentaacetate 
• 2037-48-1 rac.-1r,3c-Diamino-4t,5c,6c-trihydroxy-cyclohexan 

Relevant articles and documents

Efficient preparation of a 1,3-diazidocyclitol as a versatile 2-deoxystreptamine precursor

A synthesis route toward 2-deoxystreptamine, a common structure in many of the clinically important aminoglycosides, is presented. Starting from p-benzoquinone and cyclopentadiene, 2-deoxystreptamine is synthesized with key steps involving Pd(0)-catalyzed

Polyfunctionalised Cyclohexanes from Dianhydrodeoxyinositols. cis-Deoxy-1,3(1,4)-inosadiamines from Benzene

A ca. 9 : 1 mixture (yield 87 - 90percent) of the stereoisomeric (1α,2α,6α)-/(1α,2β,6α)-2-bromo-7-oxa-bicyclohept-3-enes (7a/8a) is obtained via controlled NBS bromination of 4,5-epoxycyclohexene (5). 7a/8a are quantitatively equilibrated in the presence of tetraalkylammonium bromides (the equilibrium being controlled by the polarity of the solvent (3 : 7 in acetonitrile) and are isolated pure by chromatography.Through selective halogen substitution (7b/8b, 9b - d/10b - d) and ammonolysis the allylic epoxy alcohols 9a/10a are obtained in high yields.Stereospecific epoxidation of 7a/8a yields the (1α,2α,3α,5α,7α)-/(1α,2β,3α,5α,7α)-diepoxy bromides 12a/14a.The latter are equilibrated quantitatively to mixtures favoring either one in the ratio of ca. 9 : 1 (CCl4) and 1 : 9 (CH3CN), respectively.Upon SN2 substitution with ammonium acylates (-> 13b, c/15b, c) and ammonolysis the naturally not occurring dianhydrodeoxyinositols 13a/15a are isolated in practically quantitative yields.The usefulness of 13a/15a and of various derivatives for the stereoselective synthesis of cis-1,4- and cis-1,3-disubstituted cyclohexanetriols is exemplified by reactions with monovalent (H2O, HI, NaN3) and divalent nucleophiles (NH2NH2, CH3NHNH2).I.a. the cis-deoxy-1,3-inosadiamines 1 (2-deoxystreptamine)/2 and the cis-deoxy-1,4-inosadiamines 3/4 become available in high yields.

REDUCTIVE ONE-STEP ELIMINATION OF AN ACETOXYL RESIDUE AT β-POSITION OF A NITRO GROUP: SYNTHESES OF (-)-SHIKIMIC ACID FROM D-MANNOSE AND 2-DEOXYSTREPTAMINE PENTAACETATE FROM N-ACETYL-D-GLUCOSAMINE

By utilizing a reductive one-step elimination reaction of an acetoxyl residue at β-position of the nitro group in cyclitols, a synthesis of the ketocyclitol triacetate (15a), which was already converted to (-)-shikimic acid (16) and (-)-guinic acid (17), from D-mannose (4) and a conversion from N-acetyl-D-glucosamine (18) to 2-deoxystreptamine pentaacetate (22) have been accomplished.