134235-13-5

Usage

Uses

Used in Pharmaceutical Industry:
Mannostatin A, Hydrochloride is used as a pharmaceutical agent for its inhibitory effects on Golgi processing mannosidase II. This makes it a valuable compound in the development of treatments for various diseases and conditions related to the malfunctioning or overactivity of this enzyme.
Used in Research Applications:
In the field of research, Mannostatin A, Hydrochloride serves as a valuable tool for studying the role of Golgi processing mannosidase II in cellular processes and its potential involvement in disease progression. Its use as a potent inhibitor allows researchers to gain a deeper understanding of the enzyme's function and its potential as a therapeutic target.
Used in Drug Development:
Mannostatin A, Hydrochloride is utilized in the development of new drugs targeting Golgi processing mannosidase II. Its effectiveness in inhibiting this enzyme makes it a promising candidate for the creation of novel therapeutics that can potentially treat a range of diseases and conditions associated with the enzyme's dysregulation.

Upstream product

• 134153-74-5 (1R,2R,3R,4R,5S)-1-(methylthio)-2,3,4-triacetoxy-5-(N-((R)-acetoxyphenylacetyl)amino)cyclopentane 
• 134566-76-0 C₁₂H₂₁NO₃S 
• 171032-11-4 1D-(1,2,3,4/5)-4-acetamido-1,2,3-tri-O-acetyl-5-(methylsulfanyl)cyclopentane-1,2,3-triol 
• 560132-83-4 1D-(1,2,3,4/5)-4-amino-1,2-O-isopropylidene-5-(methylsulfanyl)-3-O,4-N-(2,2,2-trichloroethylidene)cyclopentane-1,2,3-triol 
• 134566-75-9 C₁₃H₁₉NO₄S 
• 134677-23-9 (3′aR,4′R,6′aS)-4′,6′a-dihydro-3′aH-spiro[cyclohexane-1,2′-cyclopenta[d][1,3]dioxole]-4′-ol 
• 134566-74-8 C₂₀H₂₄INO₅ 
• 134593-75-2 C₂₁H₂₇NO₄S 
• 134566-77-1 C₁₂H₁₆INO₄ 
• 134153-71-2 (1R,4S,7R)-3-(2-(R)-hydroxy-2-phenylacetyl)-7-(methylthio)-2-oxa-3-azabicyclo<2.2.1>hept-5-ene 
• 134153-73-4 (1R,2R,5S)-1-(methylthio)-2-acetoxy-5-(N-((R)-acetoxyphenylacetyl)amino)cyclopent-3-ene 
• 134153-75-6 (1R,2R,5S)-1-(methylthio)-2-hydroxy-5-(N-((R)-hydroxyphenylacetyl)amino)cyclopent-3-ene 
• 124412-11-9 1-(methylthio)cyclopenta-2,4-diene 
• 213406-10-1 (3S,4R,5S)-4-acetylamino-3-tert-butyldimethylsilyloxy-5-ethoxycarbonyloxy-1-cyclopentene 

Downstream Products

• 102822-56-0 mannostatin A 
• 912281-48-2 4-[4-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)-benzyloxycarbonyl]amino-5-(methylsulfanyl)cyclopentane-1,2,3-triol 

Relevant academic research and scientific papers

Methanesulfenyl Triflate Promoted Iminosulfenylation of an Allylic Trichloroacetimidate. An Efficient and Stereospecific Total Synthesis of (+) Mannostatin A.

The stereospecific synthesis of glycoprotein processing enzyme inhibitor (+) mannostatin A 1 was achieved in ten steps from D-ribonolactone 9 (ca. 39percent overall yield).The strategy featured methanesulfenyl triflate mediated intramolecular cyclization of allylic N-sulfenylimidate 12.

Cyclopentanes from N-amino-glyconolactams. A synthesis of mannostatin A

Oxidation of a N-amino-ribonolactam with lead tetraacetate yields two cyclopentanes; the major one was transformed into the α-mannosidase inhibitor mannostatin A.

Synthesis and oxidation of N-aminoglyconolactams: A synthesis of mannostatin A

The N-amino-ribono-1,5-lactam 4 was prepared in two high-yielding steps from the known methanesulfonate 2. Oxidation of 4 with t-BuOCl in the presence of 2,6-lutidine afforded the tetrazene 6 (63%). Oxidation with MnO2 gave the deaminated lactam 7 (40%), which was also obtained, together with the lactone 8, upon oxidation of 4 with PhSeO2H. Oxidation with Mn(OAc)3/Cu(OAc)2 provided the lactam 7 as the major and the dimer 9 as the minor product. Oxidation of 4 with 3 equiv. of Pb(OAc)4 in toluene at room temperature gave two cyclopentanes, viz. the acetoxy epoxide 10 and the diazo ketone 11 in a combined yield of 78%. Oxidation with Pb(OBz) 4 provided 11 and the crystalline benzoyloxy epoxide 12. The crystal structure of 12 was established by X-ray analysis. The N-amino-glyconolactams 41, 46, and 51 were prepared similarly to 4. Their oxidation with Pb(OAc)4 provided the diazo ketones 56, 57, and 58 as the only isolable products. Oxidation of the N-amino-mannono-1,5-lactam 55 with Pb(OAc)4 in the presence of DMSO gave the sulfoximine 59. Mannostatin A, a strong α-mannosidase inhibitor, was synthesized from the acetoxy epoxide 10 (obtained in 48% from 4) in seven steps and in an overall yield of 45%.

Preparation of optically active derivatives of (1,4/2,3,5)- and (1,2,3,4,5/0)-5-aminocyclopentane-1,2,3,4-tetraols: synthesis of mannostatin A and its enantiomer

Diastereoselective acylation of the 2,3-O-cyclohexanediyl derivatives of (1,4/2,3,5)- and (1,2,3,4,5/0)-5-acetamidocyclopentane-1,2,3,4-tetraols with some optically active chiral acids afforded, with moderate diastereoselectivity, the chiral monoesters useful as synthetic intermediates, from which mannostatin A and its enantiomer were synthesized.

Synthetic studies on mannostatin A and its derivatives: A new family of glycoprotein processing inhibitors

Mannostatin A (1) is a naturally-occurring α-mannosidase inhibitor whose carbocyclic structure represents a significant departure from known alkaloid-based glycosidase inhibitors. The total synthesis of 1 [(1R,2R,3R,4R,5S)-1-(methylthio)-2,3,4-trihydroxy-

Synthesis of the Mannosidase II Inhibitor Mannostatin A

The synthesis of mannostatin A (1), a new inhibitor of glycoprotein processing, has been accomplished in stereocontrolled fashion starting from D-ribonolactone, 7 (ca. 32percent overall yield).