(3,4,5-Triacetyloxy-6-sulfanyloxan-2-yl)methyl acetate

Base Information

• Chemical Name: (3,4,5-Triacetyloxy-6-sulfanyloxan-2-yl)methyl acetate
• CAS No.: 19879-84-6
• Molecular Formula: C14H20O9S
• Molecular Weight: 364.373
• Hs Code.: 29329990
• NSC Number: 97032
• Mol file: 19879-84-6.mol

Synonyms:(3,4,5-triacetyloxy-6-sulfanyloxan-2-yl)methyl acetate;(3,4,5-triacetyloxy-6-sulfanyl-oxan-2-yl)methyl ethanoate;1-Thio-beta-D-Glucopyranose 2,3,4,6-Tetraacetate;SCHEMBL2353098;NSC97032;NSC-97032;PD131294;SY063541;FT-0608317;2,3,4,6-Tetra-O-acetyl-beta-D-thioglucopyranose

Chemical Property of (3,4,5-Triacetyloxy-6-sulfanyloxan-2-yl)methyl acetate

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 1.9E-07mmHg at 25°C
• Melting Point: 115-117 °C(lit.)
• Refractive Index: 1.502
• Boiling Point: 425.5 °C at 760 mmHg
• PKA: 8.42±0.70(Predicted)
• Flash Point: 298 °C
• PSA: 153.23000
• Density: 1.32 g/cm³
• LogP: -0.00070
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate
• Water Solubility.: Soluble in water and chloroform (50 mg/ml).
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 9
• Exact Mass: 364.08280338
• Heavy Atom Count: 24
• Complexity: 507

Purity/Quality:

98% ^*data from raw suppliers

2,3,4,6-Tetra-O-acetyl-b-D-thioglucopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)S)OC(=O)C)OC(=O)C)OC(=O)C
• Uses: A synthetic intermediate. 1-Thio-beta-D-glucose tetraacetate is used as an inhibitor of the Maillard reaction between glucose and glycine.

Technology Process of (3,4,5-Triacetyloxy-6-sulfanyloxan-2-yl)methyl acetate

There total 72 articles about (3,4,5-Triacetyloxy-6-sulfanyloxan-2-yl)methyl acetate 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-β-D-glucopyranosyl isothiouronium bromide (40591-65-9) → tetraacetyl thioglucose (19879-84-6)

Guidance literature:

With sodium hydrogensulfite; In water; at 0 ℃; for 2h;

Reference yield: 98.0%

O2,O3,O4,O6,S-Pentaacetyl-1-thio-β-D-glucopyranose (6806-56-0,13639-50-4,51898-27-2,62860-10-0,63783-77-7,92217-67-9,92217-68-0,130796-15-5) → tetraacetyl thioglucose (19879-84-6)

Guidance literature:

With 1,4-dithio-L-threitol; In N,N-dimethyl acetamide; at 20 ℃; for 1h; Reagent/catalyst; Solvent; chemoselective reaction; Alkaline conditions;

DOI:10.1039/c5gc00084j

Reference yield: 92.0%

C15H21BrN2O9S → tetraacetyl thioglucose (19879-84-6)

Guidance literature:

With sodium metabisulfite; In dichloromethane; water; at 60 ℃; for 3h; Inert atmosphere;

DOI:10.1039/c2cc30510k

upstream raw materials:

2-S-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-2-thiopseudourea hydrobromide

2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl chloride

acetobromomannose

1-S-acetyl-2,3,4,6-tetra-O-acetyl-1-deoxy-1-thio-α-D-mannopyranoside

Downstream raw materials:

O²,O³,O⁴,O⁶,S-Pentaacetyl-1-thio-β-D-glucopyranose

benzyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside

1-(4-bromo-phenyl)-2-(tetra-O-acetyl-β-D-glucopyranosylmercapto)-ethanone

6-(benzyloxycarbonylamino)hexyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside

Refernces

• 1、 Fujihira, Takayoshi,Arakawa, Gen,Kamijo, Haruo,Takido, Toshio,Seno, Manabu. "Synthesis of tetra-O-acetyl-1-thio-α-D-glucopyranose by reaction of tetra-O-acetyl-α-D-glucopyranosyl bromide with N,N-dimethylthioformamide". . p. 73 - 78. Retrieved 2003.
• 2、 Wang, Cang,Ren, Peng-Fei,Huang, Xiao-Jun,Wu, Jian,Xu, Zhi-Kang. "Surface glycosylation of polymer membrane by thiol-yne click chemistry for affinity adsorption of lectin". . p. 3930 - 3932. Retrieved 2011.
• 3、 Dong, Hai,Feng, Guang-Jing,Luo, tao,Lv, Jian,Wang, Shuang-Shuang,Wu, Yuzhou. "Improved Synthesis of 1-Glycosyl Thioacetates and Its Application in the Synthesis of Thioglucoside Gliflozin Analogues". . p. 2940 - 2949. Retrieved 2021/07/26.
• 4、 -. "Preparation method and application of peracetyl-protected 1-thioglucose and glucose 1-mercaptan". Paragraph 0060-0062. . Retrieved 2021/03/24.