Mannose triflate

Base Information

• Chemical Name: Mannose triflate
• CAS No.: 92051-23-5
• Molecular Formula: C15H19F3O12S
• Molecular Weight: 480.37
• Hs Code.: 29329990
• UNII: 0KI8FFQ6TT
• DSSTox Substance ID: DTXSID00238841
• Nikkaji Number: J209.267K
• Wikidata: Q27236900
• Mol file: 92051-23-5.mol

Synonyms:92051-23-5;Mannose triflate;TATM;1,3,4,6-Tetra-O-acetyl-2-O-(trifluoromethanesulfonyl)-beta-D-mannopyranose;1,3,4,6-Tetra-O-acetyl-2-O-trifluoromethanesulfonyl-b-D-mannopyranose;1,3,4,6-Tetra-O-acetyl-2-O-trifluoromethanesulfonyl-beta-D-mannopyranose;UNII-0KI8FFQ6TT;0KI8FFQ6TT;beta-D-Mannopyranose 1,3,4,6-tetra-O-acetate 2-O-trifluoromethanesulfonate;[(2R,3R,4S,5S,6S)-3,4,6-triacetyloxy-5-(trifluoromethylsulfonyloxy)oxan-2-yl]methyl acetate;1,3,4,6-Tetra-o-acetyl-2-o-trifluoro-methanesulfonyl-beta-D-mannopyranose;(2S,3S,4S,5R,6R)-6-(Acetoxymethyl)-3-(((trifluoromethyl)sulfonyl)oxy)tetrahydro-2H-pyran-2,4,5-triyl triacetate;1,3,4,6-Tetra-O-acetyl-2-(trifluoromethylsulfonyl)betad-mannopyranose;1,3,4,6-Tetra-O-acetyl-2-O-trifluoromethanesulfonylbetad-mannopyranose;beta-D-Mannopyranose, 1,3,4,6-tetraacetate 2-(trifluoromethanesulfonate);SCHEMBL543667;DTXSID00238841;1,3,4,6-Tetra-O-acetyl-2-O-trifluoromethylsulfonyl-b-D-mannopyranose;AKOS016010527;AKOS024418732;AS-15940;CS-0017907;T2307;Mannose triflate, For PET imaging, >=98% (TLC);W-204068;Q27236900;1,3,4,6-Tetra-O-acetyl-2-O-trifluormethanesulfonyl-beta-D-mannopyranose;1,3,4,6-Tetra-O-acetyl-2-O-trifluoromethanesulfonyl-?-D-mannopyranose;1,3,4,6-tetraacetate-2-(trifluoromethane-sulphonate)-beta-D-mannopyranose;b-D-Mannopyranose, 1,3,4,6-tetraacetate 2-(trifluoromethanesulfonate);b-D-Mannopyranose,1,3,4,6-tetraacetate 2-(trifluoromethanesulfonate);.BETA.-D-MANNOPYRANOSE 1,3,4,6-TETRA-O-ACETATE 2-O-TRIFLUOROMETHANESULFONATE;.BETA.-D-MANNOPYRANOSE, 1,3,4,6-TETRAACETATE 2-(TRIFLUOROMETHANESULFONATE);1,3,4,6-TETRA-O-ACETYL-2-(TRIFLUOROMETHYLSULFONYL)-.BETA.-D-MANNOPYRANOSE;1,3,4,6-TETRA-O-ACETYL-2-O-TRIFLUOROMETHANESULFONYL-.BETA.-D-MANNOPYRANOSE;beta-D-Mannopyranose 1,3,4,6-tetra-O-acetate 2-O-trifluoromethanesulfonate, 98%;Tetra-O-acetyl-mannose triflate, European Pharmacopoeia (EP) Reference Standard;(2S,3S,4S,5R,6R)-6-(Acetoxymethyl)-3-(((trifluoromethyl)sulfonyl)oxy)tetrahydro-2H-pyran-2,4,5-triyltriacetate;(2S,3S,4S,5R,6R)-6-(acetoxymethyl)-3-(trifluoromethylsulfonyloxy)tetrahydro-2H-pyran-2,4,5-triyl triacetate

Chemical Property of Mannose triflate

Chemical Property:

• Appearance/Colour: Beige crystal
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 118-122 °C
• Refractive Index: -16 ° (C=1, CHCl3)
• Boiling Point: 481.597 °C at 760 mmHg
• Flash Point: 245.061 °C
• PSA: 166.18000
• Density: 1.505 g/cm³
• LogP: 1.01650
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 11
• Exact Mass: 480.05493170
• Heavy Atom Count: 31
• Complexity: 803

Purity/Quality:

98% ^*data from raw suppliers

1,3,4,6-Tetra-O-acetyl-2-O-trifluoromethanesulfonyl-b-D-mannopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)OC(=O)C)OS(=O)(=O)C(F)(F)F)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@@H]([C@@H](O1)OC(=O)C)OS(=O)(=O)C(F)(F)F)OC(=O)C)OC(=O)C
• Physical properties: White to off-white powder or crystal
• Uses: 1,3,4,6-Tetra-O-acetyl-2-O-trifluoromethanesulfonyl-beta-D-mannopyranose is a radiolabelled pharmaceutical preparation for diagnostic aims used in positron emission tomography.

Technology Process of Mannose triflate

There total 6 articles about Mannose triflate 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: 97.5%

trifluoromethylsulfonic anhydride (358-23-6) + 1,3,4,6-tetra-O-acetyl-β-D-mannopyranose (18968-05-3) → 1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose (92051-23-5)

Guidance literature:

With pyridine; In dichloromethane; -15 deg C to 5 deg C;

DOI:10.1016/S0040-4020(01)88331-9

Reference yield:

1,3,4,6-tetra-O-acetyl-β-D-mannopyranose (18968-05-3) → 1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose (92051-23-5)

Guidance literature:

With pyridine; trifluoromethanesulfonic acid anhydride; In dichloromethane;

Reference yield:

3,4,6-tri-O-acetyl-1,2-O-(1-ethoxyethylidene)-β-D-mannopyranoside (28140-37-6) → 1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose (92051-23-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 32.4 percent / 1N aq. HCl / acetone / 0.08 h / 20 °C

2: 97.5 percent / pyridine / CH₂Cl₂ / -15 deg C to 5 deg C

With pyridine; hydrogenchloride; In dichloromethane; acetone;

DOI:10.1016/S0040-4020(01)88331-9

upstream raw materials:

trifluoromethylsulfonic anhydride

1,3,4,6-tetra-O-acetyl-β-D-mannopyranose

D-Mannose pentaacetate

3,4,6-tri-O-acetyl-1,2-O-(1-ethoxyethylidene)-β-D-mannopyranoside

Refernces

• 1、 Fadlan, Arif,Tanimoto, Hiroki,Ito, Tatsuya,Aritomi, Yusuke,Ueno, Maho,Tokuda, Masaya,Hirohara, Shiho,Obata, Makoto,Morimoto, Tsumoru,Kakiuchi, Kiyomi. "Synthesis, photophysical properties, and photodynamic activity of positional isomers of TFPP-glucose conjugates". supporting information. p. 1848 - 1858. Retrieved 2018/03/06.
• 2、 Sasaki, Eita,Ogasawara, Yasushi,Liu, Hung-Wen. "A biosynthetic pathway for BE-7585A, a 2-thiosugar-containing angucycline-type natural product". experimental part. p. 7405 - 7417. Retrieved 2010/08/05.