Methyl4,5,7,8,9-penta-O-acetyl-2,6-anhydro-3-deoxy-D-glycero-D-galacto-non-2-enonate

Base Information

• Chemical Name: Methyl4,5,7,8,9-penta-O-acetyl-2,6-anhydro-3-deoxy-D-glycero-D-galacto-non-2-enonate
• CAS No.: 136737-07-0
• Molecular Formula: C20H26O13
• Molecular Weight: 474.41
• Mol file: 136737-07-0.mol

Synonyms:Methyl4,5,7,8,9-penta-O-acetyl-2,6-anhydro-3-deoxy-D-glycero-D-galacto-non-2-enonate

Chemical Property of Methyl4,5,7,8,9-penta-O-acetyl-2,6-anhydro-3-deoxy-D-glycero-D-galacto-non-2-enonate

Chemical Property:

• Boiling Point: 503.5±50.0 °C(Predicted)
• PSA: 167.03000
• Density: 1.32±0.1 g/cm3(Predicted)
• LogP: -0.26800
• Solubility.: Chloroform, Dichloromethane

Purity/Quality:

98% ^*data from raw suppliers

Methyl 4,5,7,8,9-penta-O-acetyl-2,6-anhydro-3-deoxy-D-glycero-D-galacto-non-2-enonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl 4,5,7,8,9-Penta-O-acetyl-2,6-anhydro-3-deoxy-D-glycero-D-galacto-non-2-enonate (cas# 136737-07-0) is a compound useful in organic synthesis.

Technology Process of Methyl4,5,7,8,9-penta-O-acetyl-2,6-anhydro-3-deoxy-D-glycero-D-galacto-non-2-enonate

There total 19 articles about Methyl4,5,7,8,9-penta-O-acetyl-2,6-anhydro-3-deoxy-D-glycero-D-galacto-non-2-enonate 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: 97.0%

methyl 4,5,7,8,9-penta-O-acetyl-2,6-anhydro-2-chloro-2,3-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate (139110-77-3) → methyl 4,5,7,8,9-penta-O-acetyl-2,3,5-trideoxy-D-glycero-D-galacto-non-2-eno-pyranosonate (136737-07-0)

Guidance literature:

With pyridine; at 50 ℃; for 1h;

DOI:10.1080/07328309908544060

Reference yield: 96.0%

C26H32O13S → methyl 4,5,7,8,9-penta-O-acetyl-2,3,5-trideoxy-D-glycero-D-galacto-non-2-eno-pyranosonate (136737-07-0)

Guidance literature:

methyl (phenyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-2-thio-D-glycero-α-D-galactonon-2-ulopyranosid)onate; With bromine; In dichloromethane; at 0 - 20 ℃; for 1h;

With triethylamine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1039/d1ob00877c

Reference yield: 63.0%

methyl (2,4,5,7,8,9-hexa-O-acetyl-3-deoxy-D-glycero-β-D-galacto-2-nonulopyranosid)onate (123843-50-5) → methyl 4,5,7,8,9-penta-O-acetyl-2,3,5-trideoxy-D-glycero-D-galacto-non-2-eno-pyranosonate (136737-07-0)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 0 ℃;

DOI:10.1016/0008-6215(92)84150-Q

upstream raw materials:

methyl (2,4,5,7,8,9-hexa-O-acetyl-3-deoxy-D-glycero-β-D-galacto-2-nonulopyranosid)onate

acetic anhydride

3-deoxy-D-glycero-β-D-galacto-non-2-ulopyranosonic acid methyl ester

methyl 4,5,7,8,9-penta-O-acetyl-2,6-anhydro-2-chloro-2,3-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

Downstream raw materials:

4-amino-2,6-anhydro-3,4-dideoxy-D-glycero-D-galacto-non-2-enonic acid

4-amino-2,6-anhydro-3,4-dideoxy-D-glycero-D-talo-non-2-enonic acid

methyl 2,6-anhydro-3-deoxy-9-O-p-toluenesulfonyl-D-glycero-D-galacto-non-2-enoate

methyl 5,7,8,9-tetra-O-acetyl-4-acetylamino-2,6-anhydro-3,4-dideoxy-D-glycero-D-talo-non-2-enonate

Refernces

• 1、 Sun, Xue-Long,Kai, Toshitsugu,Sato, Noriko,Takayanagi, Hiroaki,Furuhata, Kimio. "Synthesis of 4-oxo and 4-hydroxyimino-4-deoxy-Kdn2en derivatives". . p. 1131 - 1138. Retrieved 1999.
• 2、 Nejatie, Ali,Akintola, Oluwafemi,Steves, Elizabeth,Shamsi Kazem Abadi, Saeideh,Moore, Margo M.,Bennet, Andrew J.. "Structurally homologous sialidases exhibit a commonality in reactivity: Glycoside hydrolase-catalyzed hydrolysis of Kdn-thioglycosides". . . Retrieved 2020/12/07.
• 3、 Crich, David,Navuluri, Chandrasekhar. "Stereoselective synthesis of α-Keto-deoxy-D-glycero-D- galactononulosonic acid glycosides by means of the 4,5-O-carbonate protecting group". supporting information; experimental part. p. 3049 - 3052. Retrieved 2010/07/05.