139626-80-5

Basic information

• Product Name: 4-Cyclohexene-1,2,3-triol,6-amino-,[1R-(1alpha,2beta,3beta,6beta)]-(9CI)
• Synonyms: 4-Cyclohexene-1,2,3-triol,6-amino-,[1R-(1alpha,2beta,3beta,6beta)]-(9CI)
• CAS NO: 139626-80-5
• Molecular Formula: C₆H₁₁NO₃
• Molecular Weight: 0
• Product Categories: AMINEPRIMARY
• Mol File: 139626-80-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-Cyclohexene-1,2,3-triol,6-amino-,[1R-(1alpha,2beta,3beta,6beta)]-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Cyclohexene-1,2,3-triol,6-amino-,[1R-(1alpha,2beta,3beta,6beta)]-(9CI)(139626-80-5)
• EPA Substance Registry System: 4-Cyclohexene-1,2,3-triol,6-amino-,[1R-(1alpha,2beta,3beta,6beta)]-(9CI)(139626-80-5)

Safety Data

• Hazardous Substances Data: 139626-80-5(Hazardous Substances Data)

Upstream product

• 144705-48-6 (+/-)-(1,3,4/2)- and (+/-)-(1,3/2,4)-1,2,3-Tri-O-acetyl-4-bromo-5-cyclohexene-1,2,3-triol 
• 129745-62-6 (+/-)-(4R,5S,6R)-4,5,6-tris([(tert-butyl)dimethylsilyl]oxy)cyclohex-2-en-1-one 
• 80178-07-0 1D-(1N,2,4/3)-1-Azido-2,3,4-tris(acetoxy)-5-cyclohexen 
• 155148-88-2 (+/-)-1-p-toluenesulfonyl-5-tert-butoxycarbonylamino-1,3-cyclohexadiene 

Downstream Products

• 78776-00-8 (+/-)-(1RS,2SR,3SR,4RS)-4-(acetylamino)cyclohex-5-ene-1,2,3-triyl triacetate 

Relevant articles and documents

Conduramine F-1 epoxides: synthesis and their glycosidase inhibitory activities

Starting from (±)-7-oxanorbornenone ((±)-14), (±)-(1RS,2RS,3SR,6SR)-6-azidocyclohex-4-en-1,2,3-triol ((±)-24) and (±)-(1RS,2RS,3SR,6RS)-6-azidocyclohex-4-en-1,2,3-triol ((±)-26) were obtained. Epoxidation of the latter cyclohexene derivative gave two epox

Search for α-glucosidase inhibitors: New N-substituted valienamine and conduramine F-1 derivatives

A solid-phase synthesis of new N-substituted valienamines has been developed and new synthesis of (±)-conduramine F-1, (-)-conduramine F-1, and (+)-ent-conduramine F-1 is presented, together with the preparation of N-benzylated conduramines F-1. N-Benzylation of both valienamine and (+)-ent-conduramine F-1 improves their inhibitory activity toward α-glucosidases significantly. The additional hydroxymethyl group makes valienamine derivatives more active than their (+)-ent-conduramine F-1 analogues.

Total asymmetric synthesis of (-)-conduramine B-1 and of its enantiomer. N-Benzyl derivatives of conduramine B-1 are β-glucosidase inhibitors

The 'naked sugars' (+)- and (-)-7-oxabicyclo[2.2.1]hept-5-en-2-one have been converted into (-)-conduramine B-1 ((-)-3) and its enantiomer (+)-3, respectively. They have been condensed with a variety of aldehydes in the presence of NaBH(OAc)3.

(1S,2S,3R,6R)-6-aminocyclohex-4-ene-1,2,3-triol (=(-)-conduramine B-1) is a selective inhibitor of α-mannosidases. Its inhibitory activity is enhanced by N-benzylation

(-)- and (+)-Conduramine B-1 ((-)- and (+)-5, resp.) have been derived from (+)- and (-)-7-oxabicyclo[2.2.1]hept-5-en-2-one ('naked sugars' of the first generation). Although (-)-5 imitates the structure of β-glucosides, it does not inhibit β-glucosidases

Synthesis of conduramines from N-tert-butoxycarbonylpyrrole

Two related synthetic strategies were devised to convert the Diels- Alder adduct 3c of Boc-pyrrole and p-toluenesulfonylacetylene into various racemic and optically pure conduramines. One process consists of the regio- and stereoselective hydroxylation of 3c to the tri- and dihydroxylated azabicyclo-[2.2.1]heptane derivatives 10b (Scheme 2) and the exo-endo mixture 13-14 (Scheme 3). Anionic fragmentation of 10b (methylmagnesium bromide) and of the 13-14 sulfone mixture (lithium bis-(trimethylsilyl)amide) generated the corresponding tri- and dihyroxylated aminocyclohexenes 17 and 16 (Scheme 3). Compound 17 is an aminocyclitol with a stereochemistry and partial aminotriol sequence identical to that found in neoinosamine. Compound 16 served as a source of the protected and free aminodiols 35b and 35a (Scheme 6), which were stereospecifically epoxidized to 36 (Scheme 6) and 40 (Scheme 7). Phenylselenide cleavage of these epoxides provided 37 (Scheme 6) and 41a (Scheme 7), which after selenoxide cycloelimination and protecting group manipulation were converted into (±)-conduramine C-1 (39a, Scheme 6) and the previously unreported, all-cis-conduramine D-1 (43a, Scheme 7). In a second process, anionic fragmentation of the bicyclic system is effected prior to introduction of the hydroxyl groups, as exemplified by the high-yielding conversion of the exo-endo mixture of azabicycloheptenes 11 and 12 into the aminocyclohexadiene 15 (Scheme 3). Osmate catalyzed cis-dihydroxylation of the derived bis-Boc derivative 20 (Scheme 4) led stereospecifically to the α-cis-diol 21 which was transformed into (±)-conduramine A-1 (27a) and its tetraacetyl derivative 27b via the epoxy compound 24. On the other hand, peracid oxidation of the diene 15 gave the β-epoxide 28 (Scheme 5) which was cleaved to the trans-diol 29 with aqueous sulfuric acid. This diol was converted into (±)-conduramine F-1 (34a) and its tetraacetyl derivative (34b) by a reaction sequence similar to that used for the other conduramine syntheses. Fractional crystallization of the diastereomeric mixture of Michael adducts obtained from (±)-3c and (-)-methyl lactate gave (-)-44a and (-)-45a both in ≤47% yield (Scheme 8). Both the carboxylic acid (+)-44b and the primary alcohol (+)-46 derived from (-)-44a were converted into (-)-3c with excess methylmagnesium bromide (ca. 40% overall yield). In the same way (-)-45a was transformed into optically pure (+)-3c. (-)-3c and (+)-3c were then converted into (-)-conduramine C-1 [(-)-39a] and (+)-conduramine D-1 [(+)-43a] by procedures identical to those used for the racemic compounds.

Synthesis of (+/-)-Conduramines from Pyrrole

The Diels-Alder product 1b, of tosylacetylene and N-tert-Boc-pyrrole, was converted into (+/-)-conduramine C-1 (22) and the tetraacetates of (+/-)-conduramine A-1 (9b) and F-1 (15b).

(±)-6-acetamido-1,2-anhydro-6-deoxy-myo-inositol: A tight-binding inhibitor and pseudosubstrate for N-acetyl-β-glucosaminidases

A five-step procedure is described for the synthesis of the title compound (N-acetylconduramine B trans-epoxide, 14) from tetra-O-acetylconduritol B [(±)-(1,3/2,4)-1,2,3,4-tetra-O-acetyl-5-cyclohexene-1,2,3,4-tetrol]. Inhibition studies with N-acetyl-β-gl

Cyclitol Reactions, IV. Synthesis of Enantiomeric Conduritols and Amino-Conduritols

The key-intermediate for all syntheses described in this paper is the 1-O-tosylate 7 of quebrachitol (1).This leads, via 8, to the 1L-conduritol B (5) and, via 13, to the 1L-conduritol F (17).Selective displacement of the equatorial tosyloxy group in comp