4-Methoxyphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-b-D-glucopyranoside

Base Information

• Chemical Name: 4-Methoxyphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-b-D-glucopyranoside
• CAS No.: 138906-41-9
• Molecular Formula: C27H27NO11
• Molecular Weight: 541.511
• Hs Code.: 29389090
• DSSTox Substance ID: DTXSID60458947
• Nikkaji Number: J2.184.329F
• Wikidata: Q82282519
• Mol file: 138906-41-9.mol

Synonyms:138906-41-9;4-Methoxyphenyl 3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside;4-Methoxyphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-b-D-glucopyranoside;(2R,3S,4R,5R,6S)-2-(Acetoxymethyl)-5-(1,3-dioxoisoindolin-2-yl)-6-(4-methoxyphenoxy)tetrahydro-2H-pyran-3,4-diyl diacetate;[(2R,3S,4R,5R,6S)-3,4-diacetyloxy-5-(1,3-dioxoisoindol-2-yl)-6-(4-methoxyphenoxy)oxan-2-yl]methyl acetate;SCHEMBL2058839;DTXSID60458947;YKSPBIYKEHIGHE-XMPCBSOPSA-N;AS-74882;M1480;D91510;(2R,3S,4R,5R,6S)-2-(Acetoxymethyl)-5-(1,3-dioxoisoindolin-2-yl)-6-(4-methoxyphenoxy)tetrahydro-2H-pyran-3,4-diyldiacetate;[(2R,3S,4R,5R,6S)-3,4-bis(acetyloxy)-5-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)-6-(4-methoxyphenoxy)oxan-2-yl]methyl acetate;4-Methoxyphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-beta-D-glucopyranoside;4-Methoxyphenyl 3-O,4-O,6-O-triacetyl-2-(1,3-dioxo-1,3-dihydro-2H-isoindole-2-yl)-2-deoxy-beta-D-glucopyranoside;beta-D-Glucopyranoside, 4-methoxyphenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-, 3,4,6-triacetate

Chemical Property of 4-Methoxyphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-b-D-glucopyranoside

Chemical Property:

• Vapor Pressure: 3.97E-17mmHg at 25°C
• Melting Point: 149 °C
• Refractive Index: 1.598
• Boiling Point: 656.8oC at 760 mmHg
• Flash Point: 351oC
• PSA: 143.97000
• Density: 1.4g/cm3
• LogP: 1.82810
• Storage Temp.: Freezer
• Solubility.: almost transparency in Chloroform
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 11
• Exact Mass: 541.15841068
• Heavy Atom Count: 39
• Complexity: 922

Purity/Quality:

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

4-Methoxyphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-b-D-glucopyranoside ^*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)N3C(=O)C4=CC=CC=C4C3=O)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)N3C(=O)C4=CC=CC=C4C3=O)OC(=O)C)OC(=O)C

Technology Process of 4-Methoxyphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-b-D-glucopyranoside

There total 11 articles about 4-Methoxyphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-b-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: 93.0%

2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranosyl N-tosyl benzimidate (1393471-68-5) + 4-methoxy-phenol (150-76-5) → 4-methoxylphenzyl 2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranoside (138906-41-9)

Guidance literature:

2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranosyl N-tosyl benzimidate; 4-methoxy-phenol; In dichloromethane; for 0.5h; Molecular sieve; Inert atmosphere;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 2h; Molecular sieve; Inert atmosphere;

DOI:10.1055/s-0031-1290920

Reference yield: 91.0%

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) + 4-methoxy-phenol (150-76-5) → 4-methoxylphenzyl 2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranoside (138906-41-9)

Guidance literature:

With boron trifluoride diethyl etherate; In 1,2-dichloro-ethane; at 0 - 50 ℃; for 3.5h; Molecular sieve; Inert atmosphere;

DOI:10.1055/s-0037-1609719

Reference yield: 89.0%

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose (10022-13-6,31505-44-9,81704-02-1,116347-84-3,131234-07-6,144300-04-9,79733-86-1) + 4-methoxy-phenol (150-76-5) → 4-methoxylphenzyl 2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranoside (138906-41-9)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20 ℃; for 25h; Molecular sieve;

upstream raw materials:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

4-methoxy-phenol

p-Methoxyphenyl 2-deoxy-2-phthalimido-β-D-glucopyranoside

acetic anhydride

Downstream raw materials:

4-methoxyphenyl 2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranoside

2-[(4aR,6S,7R,8R,8aS)-6-(4-Methoxy-phenoxy)-2,2-dimethyl-8-prop-2-ynyloxy-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-isoindole-1,3-dione

p-methoxyphenyl 4,6-O-diacetyl-2-deoxy-2-phthalimido-3-O-propargyl-β-D-glucopyranoside

2-[(4aR,6S,7R,8R,8aS)-6-(4-Methoxy-phenoxy)-2,2-dimethyl-8-(3-triisopropylsilanyl-prop-2-ynyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-isoindole-1,3-dione

Refernces

• 1、 -. "NOVEL INTERMEDIATES FOR THE PREPARATION OF GBS POLYSACCHARIDE ANTIGENS". Paragraph 0066-0068. . Retrieved 2019/01/30.
• 2、 Li, Wei,Gao, Yu,Li, Qing,Li, Zhong-Jun. "Ionic-liquid supported rapid synthesis of an: N -glycan core pentasaccharide on a 10 g scale". supporting information. p. 4720 - 4727. Retrieved 2018/07/06.