4-Methoxyphenyl 2,3,4,6-Tetra-O-acetyl-alpha-D-mannopyranoside

Base Information

• Chemical Name: 4-Methoxyphenyl 2,3,4,6-Tetra-O-acetyl-alpha-D-mannopyranoside
• CAS No.: 17042-40-9
• Molecular Formula: C21H26 O11
• Molecular Weight: 454.431
• Hs Code.: 29389090
• DSSTox Substance ID: DTXSID30536903
• Nikkaji Number: J1.519.113I
• Wikidata: Q72517715
• Mol file: 17042-40-9.mol

Synonyms:17042-40-9;4-Methoxyphenyl 2,3,4,6-Tetra-O-acetyl-alpha-D-mannopyranoside;(2R,3R,4S,5S,6R)-2-(Acetoxymethyl)-6-(4-methoxyphenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate;4-Methoxyphenyl 2,3,4,6-tetra-O-acetyl-a-D-mannopyranoside;[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(4-methoxyphenoxy)oxan-2-yl]methyl acetate;4-Methoxyphenyl 2,3,4,6-tetra-O-acetyl-|A-D-mannopyranoside;[(2R,3R,4S,5S,6R)-3,4,5-TRIS(ACETYLOXY)-6-(4-METHOXYPHENOXY)OXAN-2-YL]METHYL ACETATE;DTXSID30536903;4-Methoxyphenyl-2,3,4,6-tetra-O-acetyl-b-D-mannopyranoside;AKOS027257508;AS-74654;CS-0214557;M1647;T71910;A882021;4-Methoxyphenyl 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranoside, 97%;(2R,3R,4S,5S,6R)-2-(Acetoxymethyl)-6-(4-methoxyphenoxy)tetrahydro-2H-pyran-3,4,5-triyltriacetate

Chemical Property of 4-Methoxyphenyl 2,3,4,6-Tetra-O-acetyl-alpha-D-mannopyranoside

Chemical Property:

• Melting Point: 102 °C
• Refractive Index: 1.523
• PSA: 132.89000
• LogP: 1.15710
• Storage Temp.: Freezer
• Solubility.: slightly sol. in Chloroform
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 12
• Exact Mass: 454.14751164
• Heavy Atom Count: 32
• Complexity: 671

Purity/Quality:

98% ^*data from raw suppliers

4-Methoxyphenyl 2,3,4,6-tetra-O-acetyl-a-D-mannopyranoside ^*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)OC2=CC=C(C=C2)OC)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)OC2=CC=C(C=C2)OC)OC(=O)C)OC(=O)C)OC(=O)C

Technology Process of 4-Methoxyphenyl 2,3,4,6-Tetra-O-acetyl-alpha-D-mannopyranoside

There total 55 articles about 4-Methoxyphenyl 2,3,4,6-Tetra-O-acetyl-alpha-D-mannopyranoside 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-d-glucopyranosyl trichloroacetimidate (74808-10-9,86520-63-0,87119-53-7,92052-29-4,121238-27-5,127061-80-7,142831-80-9) + 4-methoxy-phenol (150-76-5) → p-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (2872-65-3,14581-81-8,17042-40-9,84380-06-3,105260-62-6)

Guidance literature:

2,3,4,6-tetra-O-acetyl-d-glucopyranosyl trichloroacetimidate; 4-methoxy-phenol; In dichloromethane; at 0 ℃; Molecular sieve; Inert atmosphere;

With boron trifluoride diethyl etherate; In dichloromethane; for 3h; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.carres.2012.09.025

Reference yield: 99.0%

4-methoxy-phenol (150-76-5) + β-D-glucose pentaacetate (604-69-3) → p-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (2872-65-3,14581-81-8,17042-40-9,84380-06-3,105260-62-6)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 16h; Inert atmosphere;

Reference yield: 98.0%

4-methoxy-phenol (150-76-5) + β-D-galactose peracetate (4163-60-4) → 4-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (2872-65-3,14581-81-8,17042-40-9,84380-06-3,105260-62-6)

Guidance literature:

With boron trifluoride diethyl etherate; triethylamine; In dichloromethane; at 0 - 20 ℃; for 16h; Inert atmosphere;

DOI:10.1002/chem.201704379

upstream raw materials:

4-methoxy-phenol

β-D-glucose pentaacetate

(4-methoxyphenoxy)trimethylsilane

1-O-trimethylsilyl-2,3,4,6-tetra-O-acetyl-D-glucoside

Downstream raw materials:

4-methoxyphenyl β-D-glucopyranoside

4-methoxyphenyl β-D-galactopyranoside

4-methoxyphenyl 4,6-O-benzylidene-β-D-galactopyranoside

p-methoxyphenyl 3-O-allyl-β-D-galactopyranoside

Refernces

• 1、 Song, Wei,Sun, Yong,Xu, Lintao,Sun, Yajing,Li, Tianlu,Peng, Peng,Lou, Hongxiang. "Synthesis of nature product kinsenoside analogues with anti-inflammatory activity". supporting information. . Retrieved 2020/12/02.
• 2、 Chen, Xi,Diaz, Sandra,Kooner, Anoopjit Singh,Santra, Abhishek,Varki, Ajit,Yu, Hai. "Chemoenzymatic Synthesis of Sialosides Containing 7- N- or 7,9-Di- N-acetyl Sialic Acid as Stable O-Acetyl Analogues for Probing Sialic Acid-Binding Proteins". . p. 14381 - 14397. Retrieved 2021/11/01.