methyl (2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxane-2-carboxylate

Base Information

• Chemical Name: methyl (2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxane-2-carboxylate
• CAS No.: 197895-54-8
• Molecular Formula: C15H18Cl3NO10
• Molecular Weight: 478.668
• DSSTox Substance ID: DTXSID70561077
• Nikkaji Number: J1.852.180F
• Wikidata: Q82444736
• Mol file: 197895-54-8.mol

Synonyms:197895-54-8;methyl (2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxane-2-carboxylate;Methyl-(2,3,4-tri-O-acetyl-beta-D-glucopyranosyl trichloroacetimidate)uronate;(2S,3S,4S,5R,6S)-2-(Methoxycarbonyl)-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate;SCHEMBL4450526;DTXSID70561077;2,3,4-Tri-O-acetyl-b-D-glucuronic Acid Methyl Ester, Trichloroacetimidate;J-012781;2,3,4-Tri-O-acetyl-?-D-glucuronic Acid Methyl Ester, Trichloroacetimidate;2,3,4-Tri-O-acetyl- beta -D-glucuronic Acid Methyl Ester, Trichloroacetimidate;methyl 2,3,4-tri-o-acetyl-1-o-(2,2,2-trichloroethanimidoyl)-beta-d-glucopyranuronate

Chemical Property of methyl (2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxane-2-carboxylate

Chemical Property:

• Melting Point: 134-138°C
• Boiling Point: 442.1±55.0 °C(Predicted)
• PKA: 1.39±0.70(Predicted)
• PSA: 147.51000
• Density: 1.59±0.1 g/cm3(Predicted)
• LogP: 1.14320
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly, Sonicated), Ethyl Acetate (Slightly)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 10
• Exact Mass: 476.999629
• Heavy Atom Count: 29
• Complexity: 680

Purity/Quality:

99%, ^*data from raw suppliers

2,3,4-Tri-O-acetyl-β-D-glucuronic Acid Methyl Ester, Trichloroacetimidate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1C(C(OC(C1OC(=O)C)OC(=N)C(Cl)(Cl)Cl)C(=O)OC)OC(=O)C
• Isomeric SMILES: CC(=O)O[C@H]1[C@@H]([C@H](O[C@H]([C@@H]1OC(=O)C)OC(=N)C(Cl)(Cl)Cl)C(=O)OC)OC(=O)C
• Uses: Intermediate for the synthesis of various glucuronide derivatives

Technology Process of methyl (2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxane-2-carboxylate

There total 8 articles about methyl (2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxane-2-carboxylate 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: 81.0%

methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate (72692-06-9,73464-50-3,3082-95-9) + trichloroacetonitrile (545-06-2) → methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetoxy)-6-[(trichloroethanimidoyl)oxy]oxane-2-carboxylate (197895-54-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 16h; Inert atmosphere;

Reference yield:

methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate (3082-96-0,5432-32-6,7355-18-2,19231-41-5,30628-06-9,30628-07-0,40268-90-4,40268-95-9,40269-24-7,104195-05-3,108032-41-3) → methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetoxy)-6-[(trichloroethanimidoyl)oxy]oxane-2-carboxylate (197895-54-8)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrazine acetate / dimethylformamide / 20 h / 55 °C

2: Cs₂CO₃ / CH₂Cl₂ / 3 h

With hydrazinium monoacetate; caesium carbonate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/anie.200460348

Reference yield:

methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate (72692-06-9,73464-50-3,3082-95-9) + trichloroacetonitrile (545-06-2) → methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate (92420-89-8) + methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetoxy)-6-[(trichloroethanimidoyl)oxy]oxane-2-carboxylate (197895-54-8)

Guidance literature:

With caesium carbonate; In dichloromethane; for 3h;

DOI:10.1002/anie.200460348

upstream raw materials:

methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate

trichloroacetonitrile

methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate

D-glucurono-6,3-lactone

Downstream raw materials:

pent-4-enyl 2-azido 4,6-O-benzylidene 2-deoxy-3-O-(methyl 2,3,4-tri-O-acetyl β-D-glucopyranosyluronate)-β-D-glucopyranoside

(2S,3R,4S,5R,6S)-6-(4-{(2R,3R)-3-[(2R)-2-acetyloxy-2-(4-fluorophenyl)ethylthio]-4-oxo-1-[4-(pyridin-3-yl)phenyl]azetidin-2-yl}phenoxy)-4,5-diacetyloxy-2-(methoxycarbonyl)-2H-3,4,5,6-tetrahydropyran-3-yl acetate

methyl (phenyl 4-deoxy-5-C-methoxy-β-D-glucopyranosid)uronate

phenyl 4-deoxy-5-C-methoxy-β-D-glucopyranosiduronic acid