89955-60-2

Usage

Chemical class

Indolizine-based tetrols
1,6,7,8-Indolizinetetrol, octahydro-, (1R,6S,7R,8R,8aR)- belongs to a class of chemical compounds that are derived from indolizine, a bicyclic organic compound.

Hydroxyl groups

Four
The molecule contains four hydroxyl (OH) groups, which contribute to its chemical properties and potential applications.

Optical activity

Yes
The compound is optically active, meaning it can rotate plane-polarized light. This is an important characteristic for pharmaceutical applications.

Configuration

(1R,6S,7R,8R,8aR)
The configuration indicates the orientation of the hydroxyl groups on the molecule. This specific arrangement of chiral centers is crucial for the compound's properties and potential applications.

Potential applications

Pharmaceutical industry
The compound has potential applications in the development of novel drugs and medical treatments, although further research and exploration are needed to fully understand its properties and uses.

Research and exploration

Ongoing
The precise properties and potential uses of this chemical compound may require additional research to fully understand its capabilities and limitations in the pharmaceutical industry.

Upstream product

• 89651-37-6 (1R,6S,7R,8R,8aR)-1,6,7,8-tetrahydroxyhexahydroindolizin-3-one 
• 102518-71-8 (3aS,8R,8aS,9R,9aS)-8-(tert-Butyl-dimethyl-silanyloxy)-9-hydroxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-f]indolizin-6-one 
• 145679-63-6 <1R,6S,7S,8R,8aR>-1-Hydroxy-6,7-(isopropylidenedioxy)-8-(methoxymethoxy)indolizidine 
• 299409-50-0 (R)-N-benzyl-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)prop-2-en-1-amine 
• 299409-44-2 N-benzyl-3-O-benzyl-5-deoxy-5-(hydroxylamino)-5-vinyl-1,2-O-isopropylidene-α-D-gluco-1,4-pentofuranoside 
• 89651-42-3 (2S,3R,4R,5S)-1-Benzyl-3,4,5-tris-benzyloxy-piperidine-2-carbaldehyde 
• 136632-69-4 5-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-β-L-idofuranurono-6,3-lactone 
• 108818-01-5 (2S,3R,4S,5S)-6-<(tert-butyldimethylsilyl)oxy>-2,3-epoxy-4,5-(isopropylidenedioxy)hexan-1-ol 
• 3969-61-7 2,3,5,6-di-isopropyIidene-1,4-dihydroxy-D-mannitol 
• 7115-22-2 1-O-benzoyl-2,3:5,6-di-O-isopropylidene-D-mannitol 
• 102487-51-4 Benzoic acid (4R,5R)-5-[(tert-butyl-dimethyl-silanyloxy)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 
• 102487-52-5 {(4R,5R)-5-[(R)-(tert-Butyl-dimethyl-silanyloxy)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-methanol 
• 102487-53-6 4-O-(tert-butyldimethylsilyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-mannose 
• 128878-75-1 ((3aR,3bS,6S,6aR,7aR)-2,2-Dimethyl-5-oxo-hexahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxol-6-yl)-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Stereoselective allylation reactions of acyclic and chiral α-amino-β-hydroxy aldehydes 3: Total synthesis of (+)-1-epi-castanospermine

Stereoselective allylation reactions of acyclic, chiral α-amino-β-hydroxy aldehydes containing four contiguous stereocenters were conducted. Allylation mediated by MgBr2?OEt2 afforded the anti-product. A plausible mechanism of the allylation reaction is also described. The resulting allylation product was used for the total synthesis of (+)-1-epi-castanospermine.

Concise synthesis of 1-epi-castanospermine

1-epi-Castanospermine (5) was synthesized from readily available 2,3,4,6-tetra-O-benzyl-1-deoxynojirimycin (11) in 9 steps and 21% overall yield, with selective debenzylation, Barbier reaction and reductive amination as the main reaction steps.

Synthesis of C1- and C8a-epimers of (+)-castanospermine from d-glucose derived γ,δ-epoxyazide: Intramolecular 5-endo epoxide opening approach

A concise synthesis of two diastereomers of (+)-castanospermine namely 1- and 8a-epi-castanospermine 1b and 1c, respectively, is reported from d-glucose. The methodology involves stereoselective cross metathesis of d-glucose derived alkene 2 with 4-bromo-

Synthesis of polyhydroxylated pyrrolizidine and indolizidine compounds and their glycosidase inhibitory activities

The synthesis of the natural product 3-epi-casuarine and two tricyclic ether bridged analogues, plus 7-deoxy-3,6-diepi-casuarine, 7-epi-australine, 1-epi-castanospermine and 1,6-diepi-castanospermine is described. The glycosidase inhibitory activities of

A flexible approach to azasugars: asymmetric total syntheses of (+)-castanospermine, (+)-7-deoxy-6-epi-castanospermine, and (+)-1-epi- castanospermine

The asymmetric total synthesis of natural azasugars (+)-castanospermine, (+)-7-deoxy-6-epI-castanospermine, and synthetic (+)-1-epi-castanospermine has been accomplished in nine to ten steps from a common chiral building block (S)-8. The method features a powerful chiral relay strategy consisting of a highly diastereoselective vinylogous Mukaiyama-type reaction with either chiral or achiral aldehydes (≥ 95% de; de = diastereomeric excess) and a diastereodivergent reduction of tetramic acids, which allows formation of three continuous stereogenic centers with high diastereo-selectivities. The method also provides a flexible access to structural arrays of 5-(α-hydroxyalkyl) tetramic acids, such as 17/34, and 5-(α-hydroxyalkyl)-4-hydroxyl-2- pyrrolidinones, such as 18 and 25/35 a. The method constitutes the first realization of the challenging chiral synthons A and D and thus of the conceptually attractive retrosynthetic analysis shown in Scheme 1 in a highly enantioselective manner.

Synthesis of (+)-1-epi-castanospermine from l-sorbose

Diastereoselective synthesis of 1-epi-castanospermine (2) from l-sorbose is described. The successful approach involved the use of 8-azido-2,8-dideoxy-α-l-gulo-oct-4-ulo-4,7-furanosononitrile intermediate (17). This compound was easily made in five steps

A concise approach to (+)-1-epi-castanospermine

A concise enantioselective synthesis of (+)-1-epi-castanospermine (2) is described, which featured the use of chiral non-racemic tetramic acid derivative 5 as a synthetic equivalent of the challenging synthon A through a highly diastereoselective vinylogo

Intramolecular 5-endo-trig aminomercuration of β-hydroxy-γ- alkenylamines: Efficient route to a pyrrolidine ring and its application for the synthesis of (+)-castanospermine and analogues

The intramolecular aminomercuration reaction of sugar-derived β-hydroxy-γ-alkenylamines 8a-c undergoes 5-endo-trig cyclization in high yield. The sugar-substituted pyrrolidines thus obtained were elaborated to the synthesis of polyhydroxylated indolizidin

Novel synthesis of castanospermine and 1-epicastanospermine

(Chemical Equation Presented) Polyhydroxylated indolizidines have potential for treatment of HIV, hepatitis C and HSV infection, multiple sclerosis, angiogenesis, cancer, and diabetes. A new synthetic approach to the title compounds from a 5-C-methoxypyra

Synthesis of (-)-7-Epiaustraline and (-)-1-Epicastanospermine

Highly efficient and selective syntheses of the title compounds are described. The cornerstone of the synthetic plan is the tandem inter [4 + 2]/inter [3 + 2] cycloaddition process. These syntheses differ from previous applications of this strategy in that they incorporate an alkylation in the hydrogenolysis step to close the second ring of the azabicyclic systems. Notable features of the sequence are (1) the highly regio- and stereoselective [3 + 2] cycloaddition of nitronate 15 with siloxymethyl (Z)-β-silylvinyl ketone (Z)-22b and (2) the highly selective reduction of the resulting ketone 24a with L-Selectride. A single-crystal X-ray structure analysis of synthetic (-)-7-epiaustraline confirmed that the targeted structure was successfully synthesized. This stimulated a reexamination of the structural assignment of the natural product. (-)-1-Epicastanospermine was synthesized in four steps from the common intermediate 27a. The absolute configuration of (-)-1-epicastanospermine was assured by single-crystal X-ray structure analysis of intermediate (-)-27a. Thus, the sign of the optical rotation had to be revised. The overall efficiency of these syntheses were 9 steps and 23% yield for (-)-7-epiaustraline and 10 steps and 20% yield for (-)-1-epicastanospermine.