3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl 2,2,2-Trichloroacetimidate

Base Information

• Chemical Name: 3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl 2,2,2-Trichloroacetimidate
• CAS No.: 87190-67-8
• Molecular Formula: C22H21Cl3N2O10
• Molecular Weight: 579.775
• Hs Code.: 2940000080
• DSSTox Substance ID: DTXSID70693706
• Wikidata: Q82622727
• Mol file: 87190-67-8.mol

Synonyms:87190-67-8;3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl 2,2,2-Trichloroacetimidate;[(2S,3S,4R,5S,6S)-3,4-diacetyloxy-5-(1,3-dioxoisoindol-2-yl)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl acetate;DTXSID70693706;T2615;3,4,6-Tri-O-acetyl-2-deoxy-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-O-(2,2,2-trichloroethanimidoyl)-alpha-L-gulopyranose

Chemical Property of 3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl 2,2,2-Trichloroacetimidate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 146°C(lit.)
• Boiling Point: 596.073°C at 760 mmHg
• Flash Point: 314.294°C
• PSA: 158.59000
• Density: 1.62g/cm³
• LogP: 2.20430
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 10
• Exact Mass: 578.026178
• Heavy Atom Count: 37
• Complexity: 947

Purity/Quality:

97% ^*data from raw suppliers

3-4-6-Tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyltrichloroacetimidate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)OC(=N)C(Cl)(Cl)Cl)N2C(=O)C3=CC=CC=C3C2=O)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@H]1[C@H]([C@@H]([C@@H]([C@@H](O1)OC(=N)C(Cl)(Cl)Cl)N2C(=O)C3=CC=CC=C3C2=O)OC(=O)C)OC(=O)C

Technology Process of 3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl 2,2,2-Trichloroacetimidate

There total 2 articles about 3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl 2,2,2-Trichloroacetimidate 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:

phthalic anhydride (85-44-9) → 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-O-trichloroacetimidate (87190-67-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: NaOMe / methanol / 0.17 h / 20 °C

1.2: Et₃N / methanol / 0.67 h / 20 - 50 °C

1.3: 40 percent / pyridine / 16 h / 20 °C

2.1: 78.9 percent / SnCl₄ / CH₂Cl₂ / 16 h / 20 °C

3.1: 90.3 percent / N-bromosuccinamide / acetone; H₂O / 1 h / 20 °C

4.1: 57 percent / K₂CO₃ / CH₂Cl₂ / 18 h / 20 °C

With N-bromosuccinamide; sodium methylate; tin(IV) chloride; potassium carbonate; In methanol; dichloromethane; water; acetone;

DOI:10.1021/ol025627w

Reference yield:

phthalic anhydride (85-44-9) → 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-O-trichloroacetimidate (87190-67-8)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium hydrogencarbonate; sodium hydroxide / methanol; water; acetone / 0 - 21 °C

2: pyridine / 16 h / 21 °C

3: acetic acid; ethylenediamine / tetrahydrofuran / 16 h / 21 °C / Inert atmosphere

4: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

With pyridine; sodium hydrogencarbonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; ethylenediamine; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; acetone;

DOI:10.1021/ol2013704

Reference yield: 99.0%

C25H25NO10 (947730-14-5) + 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-O-trichloroacetimidate (87190-67-8) → p-methoxyphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->6)-3,4-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (1225290-07-2)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -40 - 20 ℃; Molecular sieve;

DOI:10.1016/j.carres.2010.01.002

upstream raw materials:

phthalic anhydride

Downstream raw materials:

methyl 2-O-benzyl-6-deoxy-4-O-methyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-D-galactopyranoside

tert-Butyldimethylsilyl-O-(3,4,6-tri-O-acetyl-2-desoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2-azido-4,6-O-benzyliden-2-desoxy-β-D-galactopyranosid

2-O-benzyl-N-benzyloxycarbonyl-3-O-(benzyloxycarbonylmethyl)-6 O-(tert-butyldimethylsilyl)-1,5-dideoxy-1,5-imino-4-O-(3',4',6'-tri-O-acetyl-2'-deoxy-2'-phthalimido-β-D-glucopyranosyl)-D-mannitol

methyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phtalimido-β-D-glucopyranosyl)-(1-3)-O-<(3,4,6-tri-O-acetyl-2-deoxy-2-phtalimido-β-D-glucopyranosyl)-(1-6)>-O-(2-O-benzoyl-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside

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