2,3,4,6-Tetra-O-acetyl-a-D-mannopyranosyltrichloroacetimidate

Base Information

• Chemical Name: 2,3,4,6-Tetra-O-acetyl-a-D-mannopyranosyltrichloroacetimidate
• CAS No.: 121238-27-5
• Molecular Formula: C16H20 Cl3 N O10
• Molecular Weight: 492.695
• Mol file: 121238-27-5.mol

Synonyms:2,3,4,6-Tetra-O-acetyl-a-D-mannopyranosyltrichloroacetimidate

Chemical Property of 2,3,4,6-Tetra-O-acetyl-a-D-mannopyranosyltrichloroacetimidate

Chemical Property:

• Melting Point: 62-64℃
• Boiling Point: 463.3±55.0 °C(Predicted)
• PKA: 1.39±0.70(Predicted)
• PSA: 143.53000
• Density: 1.55±0.1 g/cm3(Predicted)
• LogP: 0.94680
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

Purity/Quality:

98%,99%, ^*data from raw suppliers

2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosylTrichloroacetimidateTechnicalgrade>80% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyl Trichloroacetimidate_x000D_Technical grade >80% (cas# 121238-27-5) is a compound useful in organic synthesis.

Technology Process of 2,3,4,6-Tetra-O-acetyl-a-D-mannopyranosyltrichloroacetimidate

There total 44 articles about 2,3,4,6-Tetra-O-acetyl-a-D-mannopyranosyltrichloroacetimidate 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: 100.0%

2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose (3947-62-4,6207-76-7,10343-06-3,19235-21-3,22554-70-7,22860-22-6,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,47339-09-3) + trichloroacetonitrile (545-06-2) → 2,3,4,6-tetra-O-acetyl-D-galactopyranosyl trichloroacetimidate (74808-10-9,86520-63-0,87119-53-7,92052-29-4,121238-27-5,142831-80-9,127061-80-7)

Guidance literature:

With potassium carbonate; In dichloromethane; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1039/c7ob01388d

Reference yield: 99.0%

2,3,4,6-tetra-O-acetyl-D-mannopyranose (3947-62-4,6207-76-7,10343-06-3,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1) + trichloroacetonitrile (545-06-2) → 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate (121238-27-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 2h;

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

Reference yield: 99.0%

2,3,4,6-tetra-O-acetyl-α-D-mannopyranose (22860-22-6) + trichloroacetonitrile (545-06-2) → 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate (121238-27-5)

Guidance literature:

With 4 A molecular sieve; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 1.5h;

DOI:10.1021/ja055891v

upstream raw materials:

2,3,4,6-tetra-O-acetyl-D-mannopyranose

trichloroacetonitrile

2,3,4,6-tetra-O-acetyl-α-D-mannopyranose

per-O-acetyl-α-D-mannopyranose

Downstream raw materials:

benzyl O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->2)-O-(4,6-di-O-benzyl-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

benzyl O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->3)-O-(4,6-di-O-benzyl-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Octyl-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->6)-2,4-di-O-benzyl-β-D-mannopyranosid

Octyl-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->6)-2-O-benzyl-4-desoxy-β-D-lyxopyranosid

Refernces

• 1、 Twibanire, Jean-D'Amour K.,Paul, Nawal K.,Grindley, T. Bruce. "Synthesis of novel types of polyester glycodendrimers as potential inhibitors of urinary tract infections". . p. 4115 - 4127. Retrieved 2015.
• 2、 Woller, Eric K.,Cloninger, Mary J.. "The lectin-binding properties of six generations of mannose-functionalized dendrimers". . p. 7 - 10. Retrieved 2002.
• 3、 Bauer, Sebastian,Becker, Miriam,Giesler, Markus,Hartmann, Laura,Janus, Kevin,Materlik, Jennifer,Pierzyna, Patrick,Schelhaas, Mario,Schelhaas, Sonja,Snyder, Nicole L.,Soria-Martinez, Laura. "Prophylactic Antiviral Activity of Sulfated Glycomimetic Oligomers and Polymers". . . Retrieved 2020.
• 4、 Ikuta, Akiko,Tanimoto, Toshiko,Koizumi, Kyoko. "Efficient chemical syntheses of branched cyclomalto-oligosaccharides using the trichloroacetimidate method". . p. 297 - 308. Retrieved 2003.
• 5、 -. "PROCESS OF SYNTHESIS OF β-6'SULFOQUINOVOSYL DIACYLGLYCEROLS". Page/Page column 11; 12. . Retrieved 2022/02/28.
• 6、 Andreana, Peter R.,Hossain, Farzana,Nishat, Sharmeen. "Synthesis of malformin-A1, C, a glycan, and an aglycon analog: Potential scaffolds for targeted cancer therapy". . . Retrieved 2022/02/21.