(2S,3R,4S,5S,6S)-6-(methoxycarbonyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate

Base Information

• Chemical Name: (2S,3R,4S,5S,6S)-6-(methoxycarbonyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate
• CAS No.: 7355-18-2
• Molecular Formula: C15H20 O11
• Molecular Weight: 376.317
• Hs Code.: 29329990
• European Community (EC) Number: 230-880-3
• DSSTox Substance ID: DTXSID501224723
• Nikkaji Number: J212.351G
• ChEMBL ID: CHEMBL490224
• Mol file: 7355-18-2.mol

Synonyms:7355-18-2;(2S,3R,4S,5S,6S)-6-(methoxycarbonyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate;Methyl 1,2,3,4-tetra-O-acetyl-beta-D-glucuronate;C15H20O11;MFCD00069834;Methyl O-tetraacetyl-beta-D-glucopyranuronate;methyl (2S,3S,4S,5R,6S)-3,4,5,6-tetraacetyloxyoxane-2-carboxylate;EINECS 230-880-3;Methyl 1,2,3,4-Tetra-O-acetyl-beta-D-glucopyranuronate;C15-H20-O11;NSC 16925;NSC 82042;SCHEMBL185606;1,2,3,4-Tetra-O-acetyl-beta-D-glucopyranuronic Acid Methyl Ester;CHEMBL490224;beta-D-Glucopyranuronic acid, methyl ester, tetraacetate;1,2,3,4-Tetra-O-acetyl-?-D-glucuronic Acid Methyl Ester;DTXSID501224723;AKOS015999785;AKOS016015698;methyl (2S,3S,4S,5R,6S)-3,4,5,6-tetraacetoxytetrahydropyran-2-carboxylate;CCG-249840;DS-17901;methyl 1,2,3,4-tetra-o-acetyl-d-glucuronate;Methyl 1234-tetra-O-acetyl-beta-D-glucuronate;1,2,3,4-Tetra-o-acetyl-ss-D-glucopyranuronate;EN300-6477762;Methyl 1,2,3,4-tetra-O-acetyl-ss-D-glucuronate;W-202276;Methyl 1,2,3,4-tetra-O-acetyl- beta -D-glucuronate;.beta.-D-Glucopyranuronic acid, methyl ester, tetraacetate;Glucopyranuronic acid, methyl ester, tetraacetate, .beta.-D-;1-O,2-O,3-O,4-O-Tetraacetyl-beta-D-glucopyranuronic acid methyl ester;METHYL (2S,3S,4S,5R,6S)-3,4,5,6-TETRAKIS(ACETYLOXY)OXANE-2-CARBOXYLATE;533934-74-6

Chemical Property of (2S,3R,4S,5S,6S)-6-(methoxycarbonyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate

Chemical Property:

• Appearance/Colour: White Powder
• Vapor Pressure: 5.25E-07mmHg at 25°C
• Melting Point: 179 °C
• Refractive Index: 8.0 ° (C=1, CHCl3)
• Boiling Point: 412.3 °C at 760 mmHg
• Flash Point: 178.4 °C
• PSA: 140.73000
• Density: 1.33 g/cm³
• LogP: -0.75750
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 10
• Exact Mass: 376.10056145
• Heavy Atom Count: 26
• Complexity: 584

Purity/Quality:

98% ^*data from raw suppliers

1,2,3,4-Tetra-O-acetyl-b-D-glucuronide methyl ester ^*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)OC(=O)C)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)OC(=O)C)C(=O)OC)OC(=O)C
• Uses: 1,2,3,4-Tetra-O-acetyl-β-D-glucuronic Acid Methyl Ester (cas# 7355-18-2) is a compound useful in organic synthesis.

Technology Process of (2S,3R,4S,5S,6S)-6-(methoxycarbonyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate

There total 58 articles about (2S,3R,4S,5S,6S)-6-(methoxycarbonyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate 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: 96.2%

methyl iodide (74-88-4) + 1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronic acid (62133-77-1,67919-37-3,83023-73-8,85165-61-3,95722-13-7,98301-58-7,103730-05-8,104195-04-2) → (2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester (7355-18-2)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; for 2h; Inert atmosphere;

Reference yield: 90.0%

methyl D-glucopyranuronate (82228-14-6) + acetyl chloride (75-36-5) → (2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester (7355-18-2)

Guidance literature:

With aluminum oxide; In acetonitrile; at 20 ℃; for 2h;

DOI:10.1016/j.carres.2005.11.035

Reference yield: 84.31%

acetic anhydride (108-24-7) + (+)-D-glucuronic acid γ-lactone → (2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester (7355-18-2)

Guidance literature:

(+)-D-glucuronic acid γ-lactone; With sodium hydroxide; In methanol; at 0 - 28 ℃; for 2h;

acetic anhydride; With triethylamine; for 0.416667h; Time; Reagent/catalyst; Temperature;

upstream raw materials:

pyridine

glucuronic acid methyl ester

acetic anhydride

sodium acetate

Downstream raw materials:

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

(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-{2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-6-yloxy}-tetrahydro-pyran-2-carboxylic acid methyl ester

methyl {(17-oxo-1,3,5[10]-estratrien-3-yl)-2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate

methyl {(17β-acetoxy-1,3,5[10]-estratrien-3-yl)-2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate

Refernces

• 1、 Izmest’ev,Andreeva,Sharipova,Kravchenko,Garifullin,Strobykina, I. Yu.,Kataev,Mironov. "Synthesis and antitubercular activity of first glucuronosyl phosphates and amidophosphates containing polymethylene chains". . p. 51 - 56. Retrieved 2017.
• 2、 Alharthi, Fahad Ayesh,Whitehead, George F.S.,Vitórica-Yrezábal, I?igo J.,Gardiner, John M.. "Solid state structure of sodium β-1-thiophenyl glucuronate identifies 5-coordinate sodium with three independent glucoronates". . . Retrieved 2021/03/29.
• 3、 Wang, Bi,Van Herck, Simon,Chen, Yong,Bai, Xiangyang,Zhong, Zifu,Deswarte, Kim,Lambrecht, Bart N.,Sanders, Niek N.,Lienenklaus, Stefan,Scheeren, Hans W.,David, Sunil A.,Kiessling, Fabian,Lammers, Twan,De Geest, Bruno G.,Shi, Yang. "Potent and Prolonged Innate Immune Activation by Enzyme-Responsive Imidazoquinoline TLR7/8 Agonist Prodrug Vesicles". supporting information. p. 12133 - 12139. Retrieved 2020/08/06.