2,3,4-Triacetate a-D-Xylopyranose 1-(2,2,2-Trichloroethanimidate)

Base Information

• Chemical Name: 2,3,4-Triacetate a-D-Xylopyranose 1-(2,2,2-Trichloroethanimidate)
• CAS No.: 128376-91-0
• Molecular Formula: C13H16Cl3NO8
• Molecular Weight: 420.631
• Mol file: 128376-91-0.mol

Synonyms:2,3,4-Triacetate a-D-Xylopyranose 1-(2,2,2-Trichloroethanimidate);2,3,4-Tri-O-acetyl-a-D-xylopyranosyl Trichloroacetimidate;2,3,4-Tri-O-acetyl-α-D-xylopyranosyl Trichloroacetimidate ;2,3,4-Triacetate

Chemical Property of 2,3,4-Triacetate a-D-Xylopyranose 1-(2,2,2-Trichloroethanimidate)

Chemical Property:

• Melting Point: 100-102°°
• Boiling Point: 395.3±52.0 °C(Predicted)
• PKA: 1.39±0.70(Predicted)
• Density: 1.58±0.1 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol

Purity/Quality:

97% ^*data from raw suppliers

2,3,4-Tri-O-acetyl-a-D-xylopyranosyl trichloroacetimidate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A xylose derivative for the treatment of proliferative disorders.

Technology Process of 2,3,4-Triacetate a-D-Xylopyranose 1-(2,2,2-Trichloroethanimidate)

There total 5 articles about 2,3,4-Triacetate a-D-Xylopyranose 1-(2,2,2-Trichloroethanimidate) 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: 91.0%

2,3,4-Tri-O-acetyl-D-xylopyranose (106820-14-8) + trichloroacetonitrile (545-06-2) → 2,3,4-tri-O-acetyl-α-D-xylopyranosyl trichloroacetimidate (128376-91-0,869848-87-3)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 4h; Inert atmosphere; Cooling with ice;

Reference yield: 82.0%

2,3,4-Tri-O-acetyl-D-xylopyranose (106820-14-8) + trichloroacetonitrile (545-06-2) → 2,3,4-tri-O-acetyl-β-D-xylopyranoside trichloroacetimidate (128377-34-4,869848-87-3) + 2,3,4-tri-O-acetyl-α-D-xylopyranosyl trichloroacetimidate (128376-91-0,869848-87-3)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at -20 ℃; for 4h;

DOI:10.1016/0008-6215(90)84167-S

Reference yield: 80.0%

trichloroacetonitrile (545-06-2) + α-D-xylopyranose tetraacetate (1233-03-0,2595-11-1,4026-34-0,4049-33-6,4049-34-7,4257-95-8,4257-98-1,4258-00-8,4627-30-9,17080-99-8,19186-37-9,25227-11-6,25243-38-3,62446-93-9,62929-49-1,67226-03-3,78087-60-2,78088-17-2,82890-16-2,86782-34-5,86782-35-6,92218-63-8,99880-95-2,108646-05-5,115939-79-2,123163-97-3,142130-89-0) → 2,3,4-tri-O-acetyl-α-D-xylopyranosyl trichloroacetimidate (128376-91-0,869848-87-3)

Guidance literature:

α-D-xylopyranose tetraacetate; With hydrazinium monoacetate; In N,N-dimethyl-formamide; at 20 ℃;

trichloroacetonitrile; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; Further stages.;

DOI:10.1021/ol0269042

upstream raw materials:

2,3,4-Tri-O-acetyl-D-xylopyranose

trichloroacetonitrile

α-D-xylopyranose tetraacetate

1,2,3,4-tetra-O-acetyl-D-xylopyranose

Downstream raw materials:

benzyl 2,3,2',3',4'-penta-O-acetyl-β-xylobioside

2''-iodobenzyl 2,3,2',3',4'-penta-O-acetyl-1-thio-β-xylobioside

2-nitrophenyl O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1<*>4)-2,3-di-O-acetyl-β-D-xylopyranoside

4-nitrophenyl tri-O-acetyl-β-D-xylopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xyloside

Refernces

• 1、 Movahhed, Sohajl,Westphal, Julia,Kempa, Alexander,Schumacher, Christian Eric,Sperlich, Julia,Neud?rfl, J?rg-Martin,Teusch, Nicole,Hochgürtel, Matthias,Schmalz, Hans-Günther. "Total Synthesis of (+)-Erogorgiaene and the Pseudopterosin A?F Aglycone via Enantioselective Cobalt-Catalyzed Hydrovinylation". . p. 11574 - 11579. Retrieved 2021/07/02.
• 2、 Liu, Han,Zhang, Yanfeng,Wei, Ruohan,Andolina, Gloria,Li, Xuechen. "Total Synthesis of Pseudomonas aeruginosa 1244 Pilin Glycan via de Novo Synthesis of Pseudaminic Acid". . p. 13420 - 13428. Retrieved 2017/10/05.