102822-56-0

Basic information

• Product Name: MANNOSTATIN A, HYDROCHLORIDE
• Synonyms: 1,2,3-cyclopentanetriol,4-amino-5-(methylthio)-,(1r-(1-alpha,2-alpha,3-alpha,;5-beta))-4-alph;mannostatin;mannostatina;MANNOSTATIN A HCL;MANNOSTATIN A, HYDROCHLORIDE;(1R)-4α-Amino-5β-(methylthio)-1α,2α,3α-cyclopentanetriol;(1R)-4α-Methylthio-5β-aminocyclopentane-1β,2β,3β-triol
• CAS NO: 102822-56-0
• Molecular Formula: C6H14ClNO3S
• Molecular Weight: 215.7
• Mol File: 102822-56-0.mol

Chemical Properties

• Boiling Point: 329.4°Cat760mmHg
• Flash Point: 153°C
• Appearance: /
• Density: 1.45g/cm³
• Vapor Pressure: 1.32E-05mmHg at 25°C
• Refractive Index: 1.631
• PKA: 13.51±0.70(Predicted)
• CAS DataBase Reference: MANNOSTATIN A, HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: MANNOSTATIN A, HYDROCHLORIDE(102822-56-0)
• EPA Substance Registry System: MANNOSTATIN A, HYDROCHLORIDE(102822-56-0)

Safety Data

• Hazardous Substances Data: 102822-56-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H13NO3S/c1-11-6-2(7)3(8)4(9)5(6)10/h2-6,8-10H,7H2,1H3/t2-,3+,4+,5+,6+/m0/s1

Upstream product

• 135105-77-0 (3aS,4R,5R,6S,6aR)-6-Amino-2,2-dimethyl-5-methylsulfanyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol 
• 560132-71-0 5-deoxy-5-hydrazino-2,3-O-isopropylidene-D-ribono-1,5-lactam 
• 560132-81-2 1D-(1,2,3/4,5)-1,2-O-isopropylidene-5-(methylsulfanyl)-4-O-(methylsulfonyl)cyclopentane-1,2,3,4-tetrol 
• 560132-75-4 1D-(1,2,3,4/5)-4-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidenecyclopentane-1,2,3,4,5-pentol 
• 560132-72-1 4-O-[(tert-butyl)dimethylsilyl]-5-deoxy-5-hydrazino-2,3-O-isopropylidene-D-ribono-1,5-lactam 
• 560132-74-3 2D-(1,5/1,2,3,4)-1-O-acetyl-1,5-anhydro-4-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidenecyclopentane-1,1,2,3,4,5-hexol 
• 560132-80-1 1D-(1,2,3/4,5)-3-O-[(tert-butyl)dimethylsilyl]-1,2-O-isopropylidene-5-(methylsulfanyl)-4-O-(methylsulfonyl)cyclopentane-1,2,3,4-tetrol 
• 560132-82-3 1D-(1,2,3/4,5)-1,2-O-isopropylidene-5-(methylsulfanyl)-4-O-(methylsulfonyl)-3-O-(2,2,2-trichloro-1-iminoethyl)cyclopentane-1,2,3,4-tetrol 
• 560132-78-7 1D-(1,2,3,4/5)-4-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidene-1-O-[(trifluoromethyl)sulfonyl]cyclopentane-1,2,3,4,5-pentol 
• 560132-79-8 1D-(1,2,3,4/5)-4-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidene-5-O-(methylsulfonyl)-1-O-[(trifluoromethyl)sulfonyl]cyclopentane-1,2,3,4,5-pentol 
• 29783-26-4 cis-4-cyclopentene-1,3-diol 
• 135075-44-4 (3aR,6aR)-3-(Toluene-4-sulfonyl)-3a,6a-dihydro-3H-cyclopentaoxazole-2,6-dione 
• 135075-49-9 N-((3aR,4R,6aS)-2,2-Dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-4-methyl-benzenesulfonamide 
• 147695-83-8 (3aR,6S,6aR)-6-Hydroxy-3-(toluene-4-sulfonyl)-3,3a,6,6a-tetrahydro-cyclopentaoxazol-2-one 

Relevant articles and documents

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.