80338-90-5

Upstream product

• 80226-74-0 (-)-(1R,2S,3S,4R)-1,2,3,4-tetraacetoxy-5-cyclohexene 
• 252316-80-6 (2S,3S)-diacetoxy-(1R,4R)-dihydroxycyclohex-5-ene 
• 4381-96-8 (+/-)-(1,3/2,4)-1,2,3,4-tetra-O-acetyl-5-cyclohexene-1,2,3,4-tetrol 
• 129829-60-3 (+)-Tetra-O-acetylconduritol F 
• 371155-83-8 (3aS,4S,7R,7aS)-3a,4,7,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,7-diol dibenzoate 
• 38643-30-0 (±)-1,2:5,6-di-O-isopropylidene-myo-inositol 
• 13035-65-9 (±)-1,6-di-O-benzyl-myo-inositol 
• 120679-73-4 (+/-)-3,4-di-O-benzyl-1,2:5,6-di-O-isopropylidene-myo-inositol 
• 115072-66-7 (±)-3,4-di-O-benzoyl-1,2:5,6-di-O-isopropylidene-myo-inositol 
• 64288-00-2 trans-cyclohexa-3,5-diene-1,2-diyl diacetate 
• 17793-95-2 cis-1,2-dihydrocatechol 
• 99756-37-3 (±)-3,6-di-O-benzoyl-1,2:4,5-di-O-isopropylidene-myo-inositol 
• 69945-44-4 (1RS,2SR,3RS,4RS)-2,3-dibromocyclohex-5-ene-1,4-diol 
• 5273-61-0 (5RS,6RS)-5,6-dibromocyclohex-2-ene-1,4-dione 

Downstream Products

• 78147-99-6 (-)-1L-Cyclohexane-1,3/2,4-tetrol 
• 18779-57-2 1,2,3,4,5,6-hexa-O-acetyl-muco-inositol 
• 2975-92-0 (+/-)-1L-cyclohexane-1,3/2,4-tetrol 
• 61825-76-1 (+/-)-1-bromo-1-deoxyconduritol F 
• 61825-76-1 (+/-)-1-bromo-1-deoxyconduritol B 
• 4381-96-8 (+/-)-tetraacetylconduritol C 
• 4381-96-8 (+/-)-1,2,3,4-tetra-O-acetylconduritol E 
• 2975-92-0 d,l-(1,2,3/4)-cyclohexanetetrol 

Relevant academic research and scientific papers

Concise synthesis of (+)-conduritol F and inositol analogues from naturally available (+)-proto-quercitol and their glucosidase inhibitory activity

An effective synthesis of (+)-conduritol F, (+)-chiro- and (+)-epi-inositols from naturally available (+)- proto-quercitol is described. This synthetic method provides a concise synthesis of cyclitols in enantiomerically pure form. Of the synthesized cyclitols, (+)-conduritol F potently inhibits type I α-glucosidase with an IC50 value of 86.1 lM, which is five times greater than the standard antidiabetic drug, acarbose.

Common-intermediate strategy for synthesis of conduritols and inositols via beta-hydroxy cyclohexenylsilanes.

[reaction: see text] Syntheses of conduritols B-D and F and d-(+)-chiro- and neo-inositols from cyclohexenylsilane intermediates are described. The key cyclohexylsilane intermediates 5 and 14 were synthesized by stereoselective olefin dihydroxylation of t

Directed dihydroxylation of cyclic allylic alcohols and trichloroacetamides using OsO4/TMEDA

The oxidation of a range of cyclic allylic alcohols and amides with OsO4/TMEDA is presented. Under these conditions, hydrogen bonding control leads to the (contrasteric) formation of the syn isomer in almost every example that was examined. Evidence for the bidentate binding of TMEDA to OsO4 is presented and a plausible mechanism described.

Facile syntheses of all possible diastereomers of conduritol and various derivatives of inositol stereoisomers in high enantiopurity from myo-inositol

Phosphoinositide-based signaling processes are crucially important in intracellular signal transduction events. Inositol phosphate analogues have been useful in probing the structure-activity relationships between inositol phosphates and biomacromolecules, and in studying biological functions of newly found inositol phosphates. Thus, a systematic and ready access to inositol stereoisomers is highly desirable. And practical and convenient syntheses of conduritols and related compounds are also important because of their biological activities and their synthetic utilities in the preparation of other bioactive molecules. We herein report the first syntheses of all possible diastereomers of conduritol and various derivatives of eight inositol stereoisomers in high enantiopurity from myo-inositol, which involve efficient enzymatic resolution of the intermediates conduritol B and C derivatives, followed by oxidation-reduction or the Mitsunobu reaction, and cis-dihydroxylation in stereo- and regioselective manners.

Catalytic behaviour of chloroperoxidase from Caldariomyces fumago in the oxidation of cyclic conjugated dienes

Chloroperoxidase from Caldariomyces fumago has been investigated as a catalyst for the oxidation of cyclic conjugated dienes. The nature of the substituents and the size of the carbocycle affect the enantioselectivity of the enzyme. An unexpected course o

Asymmetric induction of conduritols via AAA reactions: Synthesis of the aminocyclohexitol of hygromycin A

Two synthetic routes towards the construction of the aminocyclohexitol moiety of hygromycin A have been developed based on palladium-catalyzed asymmetric alkylation of conduritol derivatives. A protocol has been established whereby this biologically relev

Facile synthetic routes to all possible enantiomeric pairs of conduritol stereoisomers via efficient enzymatic resolution of conduritol B and C derivatives

matrix presented The first synthesis of all possible enantiomeric pairs of conduritol stereoisomers has been accomplished by efficient enzymatic resolution of conduritol B and C derivatives, followed by oxidation/reduction and the Mitsunobu reaction in st

A norbornyl route to cyclohexitols: Stereoselective synthesis of conduritol-E, allo-inositol, MK 7607 and gabosines

A novel fragmentation sequence within the norbornane system, involving C1-C7 bond scission, provides convenient access to a highly functionalized and versatile cyclohexenoid building block which has been further elaborated to a range of cyclohexitols such as, conduritol E, allo-inositol and gabosine B. Our synthesis of the structure corresponding to gabosine K indicates that the structure of this natural product needs to be revised. (C) 2000 Elsevier Science Ltd.

Enzymatic resolution of (±)-conduritol-B, a key intermediate for the synthesis of glycosidase inhibitors

Lipases from porcine pancreas, Candida cylindracea and Mucor miehei (adsorbed on support, Lipozyme IM) catalysed in t-butylmethylether the alcoholysis of rac-conduritol-B peracetate, (±)-1, by n-butanol to give enantiopure (2S,3S)-diacetoxy-(1R,4R)-dihydroxycyclohex-5-ene, (-)-3, and (1S,2R,3R,4S)-tetraacetoxy-cyclohex-5-ene, (+)-1. The enantioforms (+)- and (-)-conduritol-B, obtained after chemical hydrolysis of (-)-3 and (+)-1, respectively, may be employed to prepare both the enantiomers of conduritol-B epoxide and cyclophellitol, powerful inhibitors of glycosidases.

Practical synthesis of all inositol stereoisomers from myo-inositol

Synthesis of six inositol stereoisomers was successfully carried out via conduritol intermediates prepared from myo-inositol. Dihydroxylation and epoxidation followed by ring opening of the conduritol B, C and F derivatives gave epi-, allo-, muco-, neo-, DL-chiro- and scyllo-inositol. The cis- inositol derivative, which may not be prepared by this approach, was synthesized in 5 steps via 2-O-benzoyl-myo-inositol orthoformate as the key intermediate.