Methyl (Phenyl 2,3,4-Tri-O-acetyl-1-thio-beta-D-glucopyranosid)uronate

Base Information

• Chemical Name: Methyl (Phenyl 2,3,4-Tri-O-acetyl-1-thio-beta-D-glucopyranosid)uronate
• CAS No.: 62812-42-4
• Molecular Formula: C19H22O9S
• Molecular Weight: 426.444
• Nikkaji Number: J1.429.331K
• Mol file: 62812-42-4.mol

Synonyms:62812-42-4;Methyl (Phenyl 2,3,4-Tri-O-acetyl-1-thio-beta-D-glucopyranosid)uronate;(2S,3S,4S,5R,6S)-2-(Methoxycarbonyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate;.beta.-D-Glucopyranosiduronic acid, phenyl 1-thio-, methyl ester, triacetate;AXUXNCRKZCBMKR-CWLGOENISA-N;Phenyl 1-thio-beta-D-glucopyranosiduronic Acid Methyl Ester 2,3,4-Triacetate;methyl(phenyl2,3,4-tri-o-acetyl-1-thio-beta-d-glucopyranosid)uronate;CS-0226036;T72732;Methyl (Phenyl 2,3,4-Tri-O-acetyl-1-thio-|A-D-glucopyranosid)uronate;Methyl(phenyl 2,3,4-tri-O-acetyl-1-thio-beta-D-glucopyranosid)uronate

Chemical Property of Methyl (Phenyl 2,3,4-Tri-O-acetyl-1-thio-beta-D-glucopyranosid)uronate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 120 °C
• Boiling Point: 494.289°C at 760 mmHg
• Flash Point: 236.669°C
• PSA: 139.73000
• Density: 1.336g/cm³
• LogP: 1.47170
• Storage Temp.: Freezer
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 10
• Exact Mass: 426.09845345
• Heavy Atom Count: 29
• Complexity: 617

Purity/Quality:

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

Phenyl1-thio-β-D-glucopyranosiduronicAcidMethylEster2,3,4-Triacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1C(C(OC(C1OC(=O)C)SC2=CC=CC=C2)C(=O)OC)OC(=O)C
• Isomeric SMILES: CC(=O)O[C@H]1[C@@H]([C@H](O[C@H]([C@@H]1OC(=O)C)SC2=CC=CC=C2)C(=O)OC)OC(=O)C
• Uses: Phenyl 1-thio-β-D-glucopyranosiduronic Acid Methyl Ester 2,3,4-Triacetate is a useful synthetic intermediate. It can be used as an intermeidate to synthesize L-ascorbic acid (vitamin C, A786990).

Technology Process of Methyl (Phenyl 2,3,4-Tri-O-acetyl-1-thio-beta-D-glucopyranosid)uronate

There total 6 articles about Methyl (Phenyl 2,3,4-Tri-O-acetyl-1-thio-beta-D-glucopyranosid)uronate 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: 78.0%

thiophenol (108-98-5) + 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester (21085-72-3) → methyl (phenyl 2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranosid)uronate (62812-42-4)

Guidance literature:

With tetrabutylammomium bromide; sodium carbonate; In ethyl acetate; at 20 ℃; for 2h;

DOI:10.1021/ja209067v

Reference yield: 61.0%

phenylthiotrimethylsilane (4551-15-9) + (2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester (7355-18-2) → methyl (phenyl 2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranosid)uronate (62812-42-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 55 ℃; for 24h;

DOI:10.1016/0008-6215(95)00304-5

Reference yield:

methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate (3082-96-0,5432-32-6,7355-18-2,19231-41-5,30628-06-9,30628-07-0,40268-90-4,40268-95-9,40269-24-7,104195-05-3,108032-41-3) → methyl (phenyl 2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranosid)uronate (62812-42-4)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen bromide; acetic anhydride / dichloromethane; acetic acid / 0 - 4 °C

2: tetrabutylammomium bromide; sodium carbonate / ethyl acetate / 2 h / 20 °C

With tetrabutylammomium bromide; hydrogen bromide; acetic anhydride; sodium carbonate; In dichloromethane; acetic acid; ethyl acetate;

DOI:10.1021/ja209067v

upstream raw materials:

potassium thiophenolate

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

phenylthiotrimethylsilane

(2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Downstream raw materials:

phenyl 1-thio-β-D-glucopyranosiduronic acid

(2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-((2S,3R,4S,5S,6R)-2-acetoxy-3,5-bis-benzoyloxy-6-benzoyloxymethyl-tetrahydro-pyran-4-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

methyl (phenyl 2,3-di-O-acetyl-4-deoxy-1-thio-α-L-threo-hex-4-enopyranosid)uronate

phenyl 4-deoxy-1-thio-α-L-threo-hex-4-enopyranosiduronic acid

Refernces

• 1、 Sarkar, Arun K.,Esko, Jeffrey D.. "Synthesis and glycosaminoglycan priming activity of three disaccharides related to the linkage region tetrasaccharide of proteoglycans". . p. 161 - 172. Retrieved 2007/10/03.