62776-30-1

Basic information

• Product Name: 1,2:4,5-cis-Dianhydrodesoxyinosit
• Synonyms: 1,2:4,5-cis-Dianhydrodesoxyinosit
• CAS NO: 62776-30-1
• Molecular Weight: 128.128
• Mol File: 62776-30-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1,2:4,5-cis-Dianhydrodesoxyinosit(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2:4,5-cis-Dianhydrodesoxyinosit(62776-30-1)
• EPA Substance Registry System: 1,2:4,5-cis-Dianhydrodesoxyinosit(62776-30-1)

Safety Data

• Hazardous Substances Data: 62776-30-1(Hazardous Substances Data)

Upstream product

• 55990-90-4 (1α,2α,3α,5α,7α)-2-Brom-4,8-dioxatricyclo<5.1.0.0^3,5>octan 
• 72598-62-0 2-bromo-7-oxabicyclo<4.1.0>hept-3-ene 
• 55990-88-0 (1α,2β,3α,5α,7α)-4,8-Dioxatricyclo<5.1.0.0^3,5>octan-2-ol-acetat 

Downstream Products

• 73488-13-8 (1α,2α,3β,4α,6β)-3,6-Diamino-1,2,4-cyclohexantriol 
• 90852-02-1 (1α,2α,3α,4β,6β)-4,6-Diiod-1,2,3-cyclohexantriol 
• 90852-03-2 (1α,2α,3β,4α,6β)-3,6-Diiod-1,2,4-cyclohexantriol 
• 90852-14-5 (1α,2α,3α,4β,6β)-4,6-Dihydrazino-1,2,3-cyclohexantriol 
• 57232-44-7 (1α,2α,3α,4α,5α)-6,7-Diazabicyclo<3.2.1>octan-2,3,4-triol 
• 90852-15-6 (1α,2α,3β,4α,6β)-3,6-Dihydrazino-1,2,4-cyclohexantriol 
• 2037-48-1 (1α,2α,3α,4β,6β)-4,6-Diamino-1,2,3-cyclohexantriol 
• 26671-58-9 (1α,2β,3β,4β,5α)-1,2,3,4,5-Cyclohexanpentol 
• 488-73-3 (1α,2β,3α,4α,5β)-1,2,3,4,5-Cyclohexanpentol 
• 112882-02-7 2,2,2-Trifluoro-1,1-diphenyl-ethanesulfinic acid (1R,2S,3S,5S,7R)-(4,8-dioxa-tricyclo[5.1.0.0^3,5]oct-2-yl) ester 

Relevant articles and documents

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.