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Cas Database

92051-23-5

92051-23-5

92051-23-5

Identification

  • Product Name:TATM

  • CAS Number: 92051-23-5

  • EINECS:

  • Molecular Weight:480.37

  • Molecular Formula: C15H19F3O12S

  • HS Code:29329990

  • Mol File:92051-23-5.mol

Synonyms:1,3,4,6-Tetra-O-acetyl-2-(trifluoromethylsulfonyl)-b-D-mannopyranose;1,3,4,6-Tetra-O-acetyl-2-O-trifluoromethanesulfonyl-b-D-mannopyranose;Mannose triflate;1,3,4,6-Tetra-O-acetyl-2-O-trifluoromethanesulfonyl-beta-D-mannopyranose;β-D-Mannopyranose 1,3,4,6-tetra-O-acetate 2-O-trifluoromethanesulfonate;

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Chemical Properties

  • Appearance/Colour:Beige crystal

  • Melting Point: 118-122 °C

  • Boiling Point: 481.597 °C at 760 mmHg

  • Flash Point:245.061 °C

  • Density: 1.505 g/cm3

  • Solubility:Chloroform (Slightly), Ethyl Acetate (Slightly)

  • Storage Temp.:−20°C

  • Vapor Pressure: 0mmHg at 25°C

  • Refractive Index: -16 ° (C=1, CHCl3)

  • BRN: 4341413

  • PSA: 166.18000

  • LogP: 1.01650

Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price view more

  • Manufacture/Brand
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  • Manufacture/Brand:AK Scientific
  • Product Description:1,3,4,6-tetra-O-Acetyl-2-O-(trifluoromethanesulfonyl)-beta-D-mannopyranose
  • Packaging:5g
  • Price:$ 728
  • Delivery:In stock
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  • Manufacture/Brand:Alichem
  • Product Description:1,3,4,6-Tetra-O-acetyl-2-O-trifluoromethanesulfonyl-b-D-mannopyranose
  • Packaging:5g
  • Price:$ 557.94
  • Delivery:In stock
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  • Manufacture/Brand:Alichem
  • Product Description:1,3,4,6-Tetra-O-acetyl-2-O-trifluoromethanesulfonyl-b-D-mannopyranose
  • Packaging:1g
  • Price:$ 198.38
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:TATM 95.00%
  • Packaging:1G
  • Price:$ 1065.03
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  • Manufacture/Brand:Apolloscientific
  • Product Description:1,3,4,6-Tetra-O-acetyl-2-O-[(trifluoromethyl)sulphonyl]-beta-D-mannopyranose
  • Packaging:100mg
  • Price:$ 95
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  • Manufacture/Brand:Arctom
  • Product Description:1,3,4,6-Tetra-O-acetyl-2-O-trifluoromethanesulfonyl-beta-D-mannopyranose
  • Packaging:1g
  • Price:$ 200
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:1,3,4,6-Tetra-O-acetyl-2-O-trifluoromethanesulfonyl-b-D-mannopyranose
  • Packaging:500 mg
  • Price:$ 200
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:1,3,4,6-Tetra-O-acetyl-2-O-trifluoromethanesulfonyl-b-D-mannopyranose
  • Packaging:1 g
  • Price:$ 350
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:1,3,4,6-Tetra-O-acetyl-2-O-trifluoromethanesulfonyl-b-D-mannopyranose
  • Packaging:2 g
  • Price:$ 550
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:1,3,4,6-Tetra-O-acetyl-2-O-trifluoromethanesulfonyl-b-D-mannopyranose
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Relevant articles and documentsAll total 11 Articles be found

Design and synthesis of substrate-mimic inhibitors of mycothiol-S-conjugate amidase from Mycobacterium tuberculosis

Metaferia, Belhu B.,Ray, Satyajit,Smith, Jeremy A.,Bewley, Carole A.

, p. 444 - 447 (2007)

The Staudinger reaction between a polymer-supported triphenylphosphine reagent and pseudo-disaccharide azides is successfully applied to synthesize a variety of substrate-mimic mycothiol analogs. Screening of this new group of analogs against the mycobacterial detoxification enzyme mycothiol-S-conjugate amidase (MCA) yielded several modest inhibitors (IC50 values around 50 μM) and provided additional structure-activity relationships for future optimization of inhibitors of MCA and its homologs.

3,4,6-Tri-O-acetyl-1,2-O-[1-(exo-ethoxy)ethyl-idene]-Β-d-manno- pyranose 0.11-hydrate

Liu, Ya-Ling,Zou, Pei,Wu, Hao,Xie, Min-Hao,Luo, Shi-Neng

, p. o338-o340 (2012/11/13)

The title compound, C16H24O10·0. 11H2O, is a key inter-mediate in the synthesis of 2-de-oxy-2-[ 18F]fluoro-d-glucose (18F-FDG), which is the most widely used mol-ecular-imaging probe for positron emission tomography (PET). The crystal structure has two independent mol-ecules (A and B) in the asymmetric unit, with closely comparable geometries. The pyran-ose ring adopts a 4 C 1 conformation [Cremer-Pople puckering parameters: Q = 0.553 (2) A?, = 16.2 (2)° and = 290.4 (8)° for mol-ecule A, and Q = 0.529 (2) A?, =15.3 (3)° and = 268.2 (9)° for mol-ecule B], and the dioxolane ring adopts an envelope conformation. The chiral centre in the dioxolane ring, introduced during the synthesis of the compound, has an R configuration, with the eth-oxy group exo to the manno-pyran-ose ring. The asymmetric unit also contains one water mol-ecule with a refined site-occupancy factor of 0.222 (8), which bridges between mol-ecules A and B via O - H?O hydrogen bonds.

Synthesis of the positron-emitting radiotracer [18F]-2-fluoro-2- deoxy-d-glucose from resin-bound perfluoroalkylsulfonates

Brown, Lynda J.,Ma, Nianchun,Bouvet, Denis R.,Champion, Sue,Gibson, Alex M.,Hu, Yulai,Jackson, Alex,Khan, Imtiaz,Millot, Nicolas,Topley, Amy C.,Wadsworth, Harry,Wynn, Duncan,Brown, Richard C. D.

scheme or table, p. 564 - 575 (2009/07/18)

A new approach to the synthesis of 2-fluoro-2-deoxy-d-glucose (FDG, [ 19/18F]-3) is described, which employs supported perfluoroalkylsulfonate precursors 33-36, where the support consists of insoluble polystyrene resin beads. Treatment of these resins with [ 19F]fluoride ion afforded protected FDG [19F]-18 as the major product, and the identities of the main byproducts were determined. Acidic removal of the acetal protecting groups from [19F]-18 was shown to produce [19F]FDG. The method has been applied to the efficient radiosynthesis of the imaging agent [18F]FDG, and was shown to produce the radiochemical tracer in good radiochemical yield (average 73%, decay corrected). The Royal Society of Chemistry 2009.

Process route upstream and downstream products

Process route

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

1,3,4,6-tetra-O-acetyl-β-D-mannopyranose
18968-05-3

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

1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose
92051-23-5

1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose

Conditions
Conditions Yield
With pyridine; In dichloromethane; -15 deg C to 5 deg C;
97.5%
With pyridine; In dichloromethane; at -20 - 20 ℃; for 2h; Inert atmosphere;
96%
With pyridine; In dichloromethane; at -20 - -10 ℃;
93%
With pyridine; In dichloromethane; at -15 - 20 ℃; Inert atmosphere;
90%
In pyridine; dichloromethane; for 1h; Ambient temperature;
60%
With pyridine; In dichloromethane; at -15 - 20 ℃; Inert atmosphere;
56%
With pyridine;
With pyridine; In dichloromethane;
With pyridine;
1,3,4,6-tetra-O-acetyl-β-D-mannopyranose
18968-05-3

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

1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose
92051-23-5

1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose

Conditions
Conditions Yield
With pyridine; trifluoromethanesulfonic acid anhydride; In dichloromethane;
1.59 g (77%)
3,4,6-tri-O-acetyl-1,2-O-(1-ethoxyethylidene)-β-D-mannopyranoside
28140-37-6

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

1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose
92051-23-5

1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose

Conditions
Conditions Yield
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;
Multi-step reaction with 2 steps
1: hydrogenchloride / water; acetone / 0.08 h / 18 - 20 °C
2: pyridine / dichloromethane / -15 - 20 °C / Inert atmosphere
With pyridine; hydrogenchloride; In dichloromethane; water; acetone;
D-Mannose
530-26-7

D-Mannose

1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose
92051-23-5

1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1: iodine / 2 h / 18 - 20 °C
2: acetic anhydride; acetic acid; hydrogen bromide / 0 - 20 °C / Inert atmosphere
3: 2,4,6-trimethyl-pyridine / acetonitrile / 20 °C / Darkness
4: hydrogenchloride / water; acetone / 0.08 h / 18 - 20 °C
5: pyridine / dichloromethane / -15 - 20 °C / Inert atmosphere
With pyridine; 2,4,6-trimethyl-pyridine; hydrogenchloride; hydrogen bromide; iodine; acetic anhydride; acetic acid; In dichloromethane; water; acetone; acetonitrile;
acetobromomannose
13242-53-0

acetobromomannose

1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose
92051-23-5

1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 2,4,6-trimethyl-pyridine / acetonitrile / 20 °C / Darkness
2: hydrogenchloride / water; acetone / 0.08 h / 18 - 20 °C
3: pyridine / dichloromethane / -15 - 20 °C / Inert atmosphere
With pyridine; 2,4,6-trimethyl-pyridine; hydrogenchloride; In dichloromethane; water; acetone; acetonitrile;
D-Mannose pentaacetate
83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5

D-Mannose pentaacetate

1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose
92051-23-5

1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 1) glacial AcOH, Ac2O, 30percent HBr/AcOH, 2) 2,4,6-trimethylpyridine / 1) 0 deg C to r.t., 4 h, 2) 14 h, r.t.
2: 32.4 percent / 1N aq. HCl / acetone / 0.08 h / 20 °C
3: 97.5 percent / pyridine / CH2Cl2 / -15 deg C to 5 deg C
With pyridine; 2,4,6-trimethyl-pyridine; hydrogenchloride; hydrogen bromide; acetic anhydride; acetic acid; In dichloromethane; acetone;
Multi-step reaction with 4 steps
1: acetic anhydride; acetic acid; hydrogen bromide / 0 - 20 °C / Inert atmosphere
2: 2,4,6-trimethyl-pyridine / acetonitrile / 20 °C / Darkness
3: hydrogenchloride / water; acetone / 0.08 h / 18 - 20 °C
4: pyridine / dichloromethane / -15 - 20 °C / Inert atmosphere
With pyridine; 2,4,6-trimethyl-pyridine; hydrogenchloride; hydrogen bromide; acetic anhydride; acetic acid; In dichloromethane; water; acetone; acetonitrile;
1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose
92051-23-5

1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose

C<sub>32</sub>H<sub>42</sub>N<sub>2</sub>O<sub>15</sub>

C32H42N2O15

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1.1: NaN3 / dimethylformamide
2.1: α,α-dichloromethyl methyl ether; ZnCl2 / CHCl3 / 60 °C
3.1: 71 percent / silver triflate; 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 14 h / -40 °C
4.1: polymer-supported Ph3P / CH2Cl2 / 0.08 h / 20 °C
4.2: CH2Cl2 / 12 h / 40 °C
With sodium azide; 2,6-di-tert-butyl-4-methylpyridine; PS-triphenylphosphine; Dichloromethyl methyl ether; silver trifluoromethanesulfonate; zinc(II) chloride; In dichloromethane; chloroform; N,N-dimethyl-formamide; 4.1: Staudinger reaction;
1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose
92051-23-5

1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose

C<sub>34</sub>H<sub>48</sub>N<sub>2</sub>O<sub>13</sub>

C34H48N2O13

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1.1: NaN3 / dimethylformamide
2.1: α,α-dichloromethyl methyl ether; ZnCl2 / CHCl3 / 60 °C
3.1: 71 percent / silver triflate; 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 14 h / -40 °C
4.1: polymer-supported Ph3P / CH2Cl2 / 0.08 h / 20 °C
4.2: CH2Cl2 / 12 h / 40 °C
With sodium azide; 2,6-di-tert-butyl-4-methylpyridine; PS-triphenylphosphine; Dichloromethyl methyl ether; silver trifluoromethanesulfonate; zinc(II) chloride; In dichloromethane; chloroform; N,N-dimethyl-formamide; 4.1: Staudinger reaction;
1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose
92051-23-5

1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose

Benzo[b]thiophene-6-carboxylic acid [(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-2-((1R,2R,3R,5S)-2,3,5-trihydroxy-5-hydroxymethyl-cyclohexyloxy)-tetrahydro-pyran-3-yl]-amide

Benzo[b]thiophene-6-carboxylic acid [(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-2-((1R,2R,3R,5S)-2,3,5-trihydroxy-5-hydroxymethyl-cyclohexyloxy)-tetrahydro-pyran-3-yl]-amide

Conditions
Conditions Yield
Multi-step reaction with 6 steps
1.1: NaN3 / dimethylformamide
2.1: α,α-dichloromethyl methyl ether; ZnCl2 / CHCl3 / 60 °C
3.1: 71 percent / silver triflate; 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 14 h / -40 °C
4.1: polymer-supported Ph3P / CH2Cl2 / 0.08 h / 20 °C
4.2: CH2Cl2 / 12 h / 40 °C
5.1: NaOMe; MeOH
6.1: TFA; water / CH2Cl2
With methanol; sodium azide; 2,6-di-tert-butyl-4-methylpyridine; PS-triphenylphosphine; Dichloromethyl methyl ether; water; sodium methylate; silver trifluoromethanesulfonate; trifluoroacetic acid; zinc(II) chloride; In dichloromethane; chloroform; N,N-dimethyl-formamide; 4.1: Staudinger reaction;
1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose
92051-23-5

1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose

C<sub>30</sub>H<sub>38</sub>ClFN<sub>2</sub>O<sub>11</sub>

C30H38ClFN2O11

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1.1: NaN3 / dimethylformamide
2.1: α,α-dichloromethyl methyl ether; ZnCl2 / CHCl3 / 60 °C
3.1: 71 percent / silver triflate; 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 14 h / -40 °C
4.1: polymer-supported Ph3P / CH2Cl2 / 0.08 h / 20 °C
4.2: CH2Cl2 / 12 h / 40 °C
5.1: NaOMe; MeOH
With methanol; sodium azide; 2,6-di-tert-butyl-4-methylpyridine; PS-triphenylphosphine; Dichloromethyl methyl ether; sodium methylate; silver trifluoromethanesulfonate; zinc(II) chloride; In dichloromethane; chloroform; N,N-dimethyl-formamide; 4.1: Staudinger reaction;

92051-23-5 Upstream products

92051-23-5 Downstream products

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