METHYL (METHYL 5-ACETAMIDO-4,7,8,9-TETRA-O-ACETYL-3,5-DIDEOXY-2-THIO-D-GLYCERO-D-GALACTO-2-NONULOPYRANOSID)ONATE

Base Information

• Chemical Name: METHYL (METHYL 5-ACETAMIDO-4,7,8,9-TETRA-O-ACETYL-3,5-DIDEOXY-2-THIO-D-GLYCERO-D-GALACTO-2-NONULOPYRANOSID)ONATE
• CAS No.: 144240-36-8
• Molecular Formula: C21H31 N O12 S
• Molecular Weight: 521.543
• Mol file: 144240-36-8.mol

Synonyms:D-glycero-D-galacto-2-Nonulopyranosidonicacid, methyl 5-(acetylamino)-3,5-dideoxy-2-thio-, methyl ester,4,7,8,9-tetraacetate

Chemical Property of METHYL (METHYL 5-ACETAMIDO-4,7,8,9-TETRA-O-ACETYL-3,5-DIDEOXY-2-THIO-D-GLYCERO-D-GALACTO-2-NONULOPYRANOSID)ONATE

Chemical Property:

• PSA: 195.13000
• LogP: 0.26140
• Storage Temp.: −20°C

Purity/Quality:

97% ^*data from raw suppliers

Methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 45-46-23/24/25-36/37/38
• Safety Statements: 53-23-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of METHYL (METHYL 5-ACETAMIDO-4,7,8,9-TETRA-O-ACETYL-3,5-DIDEOXY-2-THIO-D-GLYCERO-D-GALACTO-2-NONULOPYRANOSID)ONATE

There total 5 articles about METHYL (METHYL 5-ACETAMIDO-4,7,8,9-TETRA-O-ACETYL-3,5-DIDEOXY-2-THIO-D-GLYCERO-D-GALACTO-2-NONULOPYRANOSID)ONATE 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: 96.0%

Trimethyl(methylthio)silane (3908-55-2) + methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate (6931-68-6,72690-21-2,74006-95-4,108740-37-0,108740-38-1,108740-39-2,119241-63-3,119241-64-4,119241-65-5,147129-72-4,147129-73-5,73208-82-9) → methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate (144240-36-8)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 50 ℃; for 6h;

DOI:10.1016/0008-6215(91)84066-N

Reference yield:

N-acetyl neuraminic acid (6813-81-6,14120-72-0,19342-33-7,21646-00-4,82349-00-6,99395-98-9,99395-99-0,99396-00-6,102734-10-1,489-46-3,140671-47-2,140850-42-6,140850-43-7,140850-44-8,145375-13-9) → methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate (144240-36-8)

Guidance literature:

Multi-step reaction with 3 steps

1: H⁺

2: pyridine

3: TMS-OTf

With trimethylsilyl trifluoromethanesulfonate; hydrogen cation; In pyridine;

DOI:10.1016/S0960-894X(97)00051-6

Reference yield:

N-acetylneuraminic acid methyl ester (20298-35-5,22900-11-4,100678-43-1,109121-98-4,109122-00-1,119241-60-0,119241-61-1,119241-62-2) → methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate (144240-36-8)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine

2: TMS-OTf

With trimethylsilyl trifluoromethanesulfonate; In pyridine;

DOI:10.1016/S0960-894X(97)00051-6

upstream raw materials:

Trimethyl(methylthio)silane

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

methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosyl)onate

(1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate

Downstream raw materials:

methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

2-(trimethylsilyl)ethyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-6-O-benzoyl-β-D-galactopyranoside

(2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-6-((1S,2R)-1,2,3-triacetoxy-propyl)-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzoyloxy-6-docosyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

(2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-6-((1S,2R)-1,2,3-triacetoxy-propyl)-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzoyloxy-6-docosyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Refernces

• 1、 Tsuji, Mitsuru,Sriwilaijaroen, Nongluk,Inoue, Hideo,Miki, Kazuhiko,Kinoshita, Kaoru,Koyama, Kiyotaka,Furuhata, Kimio,Suzuki, Yasuo,Takahashi, Kunio. "Synthesis and anti-influenza virus evaluation of triterpene-sialic acid conjugates". . p. 17 - 24. Retrieved 2017/12/06.
• 2、 Kuznik,Hoersch,Kretzschmar,Unverzagt. "Chemical and enzymatic synthesis of high-affinity selectin ligands". . p. 577 - 580. Retrieved 2007/10/03.