Methyl 2,3,4,6-Tetra-O-acetyl-1-thio-beta-D-glucopyranoside

Base Information

• Chemical Name: Methyl 2,3,4,6-Tetra-O-acetyl-1-thio-beta-D-glucopyranoside
• CAS No.: 13350-45-3
• Molecular Formula: C15H22 O9 S
• Molecular Weight: 378.4
• Hs Code.: 29329990
• DSSTox Substance ID: DTXSID60457435
• Nikkaji Number: J1.033.911A
• Wikidata: Q82280278
• Mol file: 13350-45-3.mol

Synonyms:13350-45-3;Methyl 2,3,4,6-Tetra-O-acetyl-1-thio-beta-D-glucopyranoside;(2R,3R,4S,5R,6S)-2-(Acetoxymethyl)-6-(methylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate;[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-methylsulfanyloxan-2-yl]methyl acetate;SCHEMBL6764694;DTXSID60457435;XWFUCHLBRWBKGN-QMIVOQANSA-N;MFCD00080807;STL507315;AKOS015911830;AS-74420;CS-0206412;M1682;T71723;beta-D-glucopyranoside,methyl 1-thio-,tetraacetate;.beta.-D-Glucopyranoside, methyl 1-thio-, tetraacetate;1-(Methylthio)-1-deoxy-beta-D-glucopyranose tetraacetate;Glucopyranoside, methyl 1-thio-, tetraacetate, .beta.-D-;Methyl 2,3,4,6-tetra-O-acetyl- beta -D-thioglucopyranoside;Methyl 2,3,4,6-Tetra-O-acetyl-1-thio-|A-D-glucopyranoside;[(2R,3R,4S,5R,6S)-3,4,5-TRIS(ACETYLOXY)-6-(METHYLSULFANYL)OXAN-2-YL]METHYL ACETATE

Chemical Property of Methyl 2,3,4,6-Tetra-O-acetyl-1-thio-beta-D-glucopyranoside

Chemical Property:

• Vapor Pressure: 5.86E-08mmHg at 25°C
• Melting Point: 91 °C
• Boiling Point: 440.5oC at 760 mmHg
• Flash Point: 206.9oC
• PSA: 139.73000
• Density: 1.29g/cm3
• LogP: 0.43250
• Storage Temp.: −20°C
• Solubility.: soluble in Chloroform
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 10
• Exact Mass: 378.09845345
• Heavy Atom Count: 25
• Complexity: 521

Purity/Quality:

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

Methyl 2,3,4,6-tetra-O-acetyl-b-D-thioglucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)SC)OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)SC)OC(=O)C)OC(=O)C)OC(=O)C

Technology Process of Methyl 2,3,4,6-Tetra-O-acetyl-1-thio-beta-D-glucopyranoside

There total 30 articles about Methyl 2,3,4,6-Tetra-O-acetyl-1-thio-beta-D-glucopyranoside 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: 99.0%

tetraacetyl thioglucose (19879-84-6) + dimethyl sulfate (77-78-1) → methyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (13350-45-3)

Guidance literature:

With triethylamine; In acetonitrile; at 30 ℃;

DOI:10.1039/d0ra09534f

Reference yield: 98.0%

acetic anhydride (108-24-7) + methyl 1-deoxy-1-thio-β-D-glucopyranoside (30760-09-9) → methyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (13350-45-3)

Guidance literature:

With methanesulfonic acid; In neat (no solvent); at 30 - 35 ℃; for 0.166667h; Green chemistry;

DOI:10.1039/c4ra16916f

Reference yield: 95.0%

Dimethyldisulphide (624-92-0) + α-D-glucopyranose peracetylate (604-68-2) → methyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (13350-45-3)

Guidance literature:

With iodine; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane; for 1.5h; Ambient temperature;

DOI:10.1080/07328309808002346

upstream raw materials:

diazomethane

diethyl ether

O²,O³,O⁴,O⁶-Tetraacetyl-1-thio-D-glucose

methyl iodide

Downstream raw materials:

(3R)-3-Acetoxy-β-ionon

methyl 4,6-O-cyclohexylidene-2,3-di-O-(benzyl-d7)-1-thio-β-D-glucopyranoside

methyl 4,6-O-cyclohexylidene-2,3-di-O-benzyl-1-thio-β-D-glucopyranoside

methyl (2,3,4,6-tetra-O-acetyl-D-glucopyranosyl)-β-(1→6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside

Refernces

• 1、 Traverssi, Miqueas G.,Pe?é?ory, Alicia B.,Varela, Oscar,Colomer, Juan P.. "Photooxidation of thiosaccharides mediated by sensitizers in aerobic and environmentally friendly conditions". . p. 9262 - 9273. Retrieved 2021/03/16.
• 2、 Dong, Yue,Ji, Peng,Zhang, Yueteng,Wang, Changqing,Meng, Xiang,Wang, Wei. "Organophotoredox-Catalyzed Formation of Alkyl-Aryl and -Alkyl C-S/Se Bonds from Coupling of Redox-Active Esters with Thio/Selenosulfonates". supporting information. p. 9562 - 9567. Retrieved 2021/01/09.