1,2,3,4,6-Penta-O-(3,4,5-tri-O-benzylgalloyl)-b-D-glucopyranose

Base Information

• Chemical Name: 1,2,3,4,6-Penta-O-(3,4,5-tri-O-benzylgalloyl)-b-D-glucopyranose
• CAS No.: 122625-60-9
• Molecular Formula: C₁₄₆H₁₂₂O₂₆
• Molecular Weight: 2292.56
• DSSTox Substance ID: DTXSID40583221
• Wikidata: Q82474750
• Mol file: 122625-60-9.mol

Synonyms:122625-60-9;1,2,3,4,6-Penta-O-(3,4,5-tri-O-benzylgalloyl)-b-D-glucopyranose;[(2R,3R,4S,5R,6S)-3,4,5,6-tetrakis[[3,4,5-tris(phenylmethoxy)benzoyl]oxy]oxan-2-yl]methyl 3,4,5-tris(phenylmethoxy)benzoate;(2S,3R,4S,5R,6R)-6-(((3,4,5-Tris(benzyloxy)benzoyl)oxy)methyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetrakis(3,4,5-tris(benzyloxy)benzoate);DXBOPZWOODFFKH-JKUAIIEZSA-N;SCHEMBL2229805;DTXSID40583221;W-200959;beta-d-glucopyranose pentakis[3,4,5-tris(phenylmethoxy)-benzoate];Pentakis[3,4,5-tris(phenylmethoxy)benzoate] beta-D-Glucopyranose;1,2,3,4,6-Penta-O-(3,4,5-tri-O-benzylgalloyl)- beta -D-glucopyranose;1,2,3,4,6-Penta-O-(3,4,5-tri-O-benzylgalloyl)-?-D-glucopyranose;1,2,3,4,6-Penta-O-(3,4,5-tri-O-benzylgalloyl)-beta-D-glucopyranose;1,2,3,4,6-Pentakis-O-[3,4,5-tris(benzyloxy)benzoyl]-beta-D-glucopyranose

Chemical Property of 1,2,3,4,6-Penta-O-(3,4,5-tri-O-benzylgalloyl)-b-D-glucopyranose

Chemical Property:

• PSA: 279.18000
• LogP: 29.78710
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly)
• XLogP3: 30
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 26
• Rotatable Bond Count: 61
• Exact Mass: 2291.82578883
• Heavy Atom Count: 172
• Complexity: 4240

Purity/Quality:

95% ^*data from raw suppliers

1,2,3,4,6-Penta-O-(3,4,5-tri-O-benzylgalloyl)-β-D-glucopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC2=CC(=CC(=C2OCC3=CC=CC=C3)OCC4=CC=CC=C4)C(=O)OCC5C(C(C(C(O5)OC(=O)C6=CC(=C(C(=C6)OCC7=CC=CC=C7)OCC8=CC=CC=C8)OCC9=CC=CC=C9)OC(=O)C1=CC(=C(C(=C1)OCC1=CC=CC=C1)OCC1=CC=CC=C1)OCC1=CC=CC=C1)OC(=O)C1=CC(=C(C(=C1)OCC1=CC=CC=C1)OCC1=CC=CC=C1)OCC1=CC=CC=C1)OC(=O)C1=CC(=C(C(=C1)OCC1=CC=CC=C1)OCC1=CC=CC=C1)OCC1=CC=CC=C1
• Isomeric SMILES: C1=CC=C(C=C1)COC2=CC(=CC(=C2OCC3=CC=CC=C3)OCC4=CC=CC=C4)C(=O)OC[C@@H]5[C@H]([C@@H]([C@H]([C@@H](O5)OC(=O)C6=CC(=C(C(=C6)OCC7=CC=CC=C7)OCC8=CC=CC=C8)OCC9=CC=CC=C9)OC(=O)C1=CC(=C(C(=C1)OCC1=CC=CC=C1)OCC1=CC=CC=C1)OCC1=CC=CC=C1)OC(=O)C1=CC(=C(C(=C1)OCC1=CC=CC=C1)OCC1=CC=CC=C1)OCC1=CC=CC=C1)OC(=O)C1=CC(=C(C(=C1)OCC1=CC=CC=C1)OCC1=CC=CC=C1)OCC1=CC=CC=C1
• General Description: **1,2,3,4,6-Penta-O-(3,4,5-tri-O-benzylgalloyl)-β-D-glucopyranose** is a synthetic derivative of β-D-glucopyranose where all five hydroxyl groups (positions 1, 2, 3, 4, and 6) are esterified with 3,4,5-tris(benzyloxy)galloyl groups. 1,2,3,4,6-Penta-O-(3,4,5-tri-O-benzylgalloyl)-b-D-glucopyranose serves as a protected intermediate in the synthesis of 1,2,3,4,6-penta-O-galloyl-β-D-glucopyranose (β-PGG), a natural product with potential biological activity. The benzyl groups provide steric protection, enabling selective deprotection to yield the desired galloylated glucose derivatives. The synthesis of such compounds is significant for exploring their antitumor and immunomodulatory properties, as seen in related galloyl- and ellagic acid-based derivatives. **Return:** 1,2,3,4,6-Penta-O-(3,4,5-tri-O-benzylgalloyl)-β-D-glucopyranose is a fully protected intermediate in the synthesis of bioactive galloylglucose derivatives, where each hydroxyl group of β-D-glucopyranose is esterified with a 3,4,5-tris(benzyloxy)galloyl moiety. This structure facilitates controlled deprotection to access natural products like penta-O-galloyl-β-D-glucose, which are studied for their antitumor and immunomodulatory effects.

Technology Process of 1,2,3,4,6-Penta-O-(3,4,5-tri-O-benzylgalloyl)-b-D-glucopyranose

There total 12 articles about 1,2,3,4,6-Penta-O-(3,4,5-tri-O-benzylgalloyl)-b-D-glucopyranose 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%

D-Glucose (2280-44-6) + 3,4,5-tris(benzyloxy)benzoyl chloride (1486-47-1) → 1,2,3,4,6-pentakis-O-(3’,4’,5’-tribenzyloxybenzoyl)-β-D-glucopyranose (70424-95-2,122625-60-9)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In acetonitrile; at 20 - 25 ℃; for 24h;

DOI:10.1002/anie.201411606

Reference yield: 96.0%

β-D-glucose (492-61-5) + 3,4,5-tris(benzyloxy)benzoyl chloride (1486-47-1) → 1,2,3,4,6-pentakis-O-(3’,4’,5’-tribenzyloxybenzoyl)-β-D-glucopyranose (70424-95-2,122625-60-9)

Guidance literature:

With dmap; In acetonitrile; at 20 ℃; for 48h;

DOI:10.1016/j.carres.2008.10.024

Reference yield: 53.0%

3,4,5-tribenzyloxybenzoic acid (1486-48-2) + 1-O-2,3,4,6-tetrakis(3,4,5-tris(benzyloxy)benzoyl)-α-D-glucopyranosyl trichloroacetimidate → 1,2,3,4,6-pentakis-O-(3’,4’,5’-tribenzyloxybenzoyl)-β-D-glucopyranose (70424-95-2,122625-60-9)

Guidance literature:

In toluene; for 18h; Heating;

DOI:10.1021/jo0010936

upstream raw materials:

D-Glucose

3,4,5-tribenzyloxybenzoic acid

3,4,5-tris(benzyloxy)benzoyl chloride

alpha-D-glucopyranose

Downstream raw materials:

tannic acid