(2S,3R,4S,5R)-2-methylpiperidine-3,4,5-triol

Base Information

• Chemical Name: (2S,3R,4S,5R)-2-methylpiperidine-3,4,5-triol
• CAS No.: 99212-30-3
• Molecular Formula: C6H14ClNO3
• Molecular Weight: 147.17
• Hs Code.: 29329990
• DSSTox Substance ID: DTXSID60912837
• Nikkaji Number: J653.804E
• Wikidata: Q27459214
• Pharos Ligand ID: 7JPS6GBSFJYZ
• Metabolomics Workbench ID: 130581
• ChEMBL ID: CHEMBL314772
• Mol file: 99212-30-3.mol

Synonyms:1,5-dideoxy-1,5-iminofucitol;deoxyfuco-nojirimycin;deoxyfuconojirimycin

Chemical Property of (2S,3R,4S,5R)-2-methylpiperidine-3,4,5-triol

Chemical Property:

• Appearance/Colour: Tan Crystalline Solid
• Vapor Pressure: 0.000462mmHg at 25°C
• Melting Point: 155-157 °C
• Refractive Index: 1.545
• Boiling Point: 311.7 °C at 760 mmHg
• Flash Point: 142.3 °C
• PSA: 72.72000
• Density: 1.297 g/cm³
• LogP: -1.61040
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility.: Methanol (Slightly, Sonicated), Water (Slightly)
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 147.08954328
• Heavy Atom Count: 10
• Complexity: 120

Purity/Quality:

99% ^*data from raw suppliers

Deoxyfuconojirimycin Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1C(C(C(CN1)O)O)O
• Isomeric SMILES: C[C@H]1[C@H]([C@H]([C@@H](CN1)O)O)O
• Uses: A powerful and specific inhibitor of several alpha-L-fucosidases selective inhibitor of a-D-galactosidase

Technology Process of (2S,3R,4S,5R)-2-methylpiperidine-3,4,5-triol

There total 80 articles about (2S,3R,4S,5R)-2-methylpiperidine-3,4,5-triol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

1,5-dideoxy-1,5-imino-3, 4-O-isopropylidene-L-fucitol (122194-06-3) → deoxyfuconojirimycin (99212-30-3,449729-69-5,528593-83-1)

Guidance literature:

With trifluoroacetic acid;

DOI:10.1016/j.carres.2005.10.002

Reference yield: 95.0%

(2S,3R,4S,5R)-1-Benzhydryl-2-methyl-piperidine-3,4,5-triol (243663-16-3) → deoxyfuconojirimycin (99212-30-3,449729-69-5,528593-83-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; ethyl acetate; at 20 ℃; for 3h;

DOI:10.1021/jo9820115

Reference yield: 91.0%

N-benzyl-2,3,4-tri-O-benzyl-1,5-dideoxy-1,5-imino-L-fucitol → deoxyfuconojirimycin (99212-30-3,449729-69-5,528593-83-1)

Guidance literature:

With hydrogenchloride; palladium 10% on activated carbon; hydrogen; In methanol; water; for 24h;

DOI:10.1016/j.bioorg.2018.12.003

upstream raw materials:

1,5-dideoxy-1,5-imino-3, 4-O-isopropylidene-L-fucitol

2,3,4-Tri-O-benzoyl-1,5-didesoxy-1,5-imino-L-fucit

(2S,3R,4S,5R)-4-Benzyloxy-2-methyl-piperidine-3,5-diol

(2S,3R,4S,5R)-1-Benzhydryl-2-methyl-piperidine-3,4,5-triol

Downstream raw materials:

1,5-Didesoxy-1,5-imino-N-<5-(methoxycarbonyl)pentyl>-L-fucit

1,5-Didesoxy-1,5-imino-N-methyl-L-fucit

N-Benzyl-1,5-didesoxy-1,5-imino-L-fucit

Refernces

• 1、 Jiang, Jianbing,Kallemeijn, Wouter W.,Wright, Daniel W.,Van Den Nieuwendijk, Adrianus M. C. H.,Rohde, Veronica Coco,Folch, Elisa Colomina,Van Den Elst, Hans,Florea, Bogdan I.,Scheij, Saskia,Donker-Koopman, Wilma E.,Verhoek, Marri,Li, Nan,Schürmann, Martin,Mink, Daniel,Boot, Rolf G.,Codée, Jeroen D. C.,Van Der Marel, Gijsbert A.,Davies, Gideon J.,Aerts, Johannes M. F. G.,Overkleeft, Herman S.. "In vitro and in vivo comparative and competitive activity-based protein profiling of GH29 α-L-fucosidases". . p. 2782 - 2789. Retrieved 2015/09/02.
• 2、 Dubernet, Mathieu,Defoin, Albert,Tarnus, Celine. "Asymmetric synthesis of the L-fuco-nojirimycin, a nanomolar α-L-fucosidase inhibitor". . p. 1172 - 1174. Retrieved 2007/10/03.