(2R,3R,4S,5R,6R)-6-((Benzoyloxy)methyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetrabenzoate

Base Information

• Chemical Name: (2R,3R,4S,5R,6R)-6-((Benzoyloxy)methyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetrabenzoate
• CAS No.: 22415-91-4
• Molecular Formula: C41H32O11
• Molecular Weight: 700.698
• Hs Code.: 29400090
• DSSTox Substance ID: DTXSID90448654
• Nikkaji Number: J1.498.598K
• Wikidata: Q82267742
• ChEMBL ID: CHEMBL380323
• Mol file: 22415-91-4.mol

Synonyms:22415-91-4;(2R,3R,4S,5R,6R)-6-((Benzoyloxy)methyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetrabenzoate;alpha-D-Glucopyranose pentabenzoate;a-D-Glucopyranose, pentabenzoate;C41H32O11;1,2,3,4,6-PENTA-O-BENZOYL-A-D-GLUCOPYRANOSE;1,2,3,4,6-Penta-O-benzoyl-alpha-D-glucopyranose;CHEMBL380323;SCHEMBL7251000;DTXSID90448654;alpha -D-Glucopyranose pentabenzoate;a-D-Glucopyranose,pentabenzoate(9ci);MFCD00010695;AKOS015919017;CS-W013786;1,2,3,4,6-Penta-O-benzoyl-alpha-D-glucose;A816185;W-201932;(2R,3R,4S,5R,6R)-6-(benzoyloxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetrabenzoate

Chemical Property of (2R,3R,4S,5R,6R)-6-((Benzoyloxy)methyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetrabenzoate

Chemical Property:

• Vapor Pressure: 7.33E-26mmHg at 25°C
• Melting Point: 185-188 °C(lit.)
• Refractive Index: 1.649
• Boiling Point: 803.729 °C at 760 mmHg
• Flash Point: 325.931 °C
• PSA: 140.73000
• Density: 1.377 g/cm³
• LogP: 6.10210
• XLogP3: 8.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 16
• Exact Mass: 700.19446183
• Heavy Atom Count: 52
• Complexity: 1190

Purity/Quality:

98%, ^*data from raw suppliers

1,2,3,4,6-Penta-O-benzoyl-a-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)C(=O)OCC2C(C(C(C(O2)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4)OC(=O)C5=CC=CC=C5)OC(=O)C6=CC=CC=C6
• Isomeric SMILES: C1=CC=C(C=C1)C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](O2)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4)OC(=O)C5=CC=CC=C5)OC(=O)C6=CC=CC=C6

Technology Process of (2R,3R,4S,5R,6R)-6-((Benzoyloxy)methyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetrabenzoate

There total 84 articles about (2R,3R,4S,5R,6R)-6-((Benzoyloxy)methyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetrabenzoate 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%

D-Glucose (2280-44-6) + benzoyl chloride (98-88-4) → 1,2,3,4,6-penta-O-benzoyl-D-glucopyranoside (2592-58-7,3006-48-2,3006-49-3,13526-09-5,14679-57-3,22415-91-4,29884-70-6,41545-55-5,41545-56-6,41569-33-9,96996-90-6,121570-85-2,121570-86-3)

Guidance literature:

dmap; In pyridine; at 0 ℃; for 20h;

DOI:10.1002/chem.200204544

Reference yield: 100.0%

D-Galactose (59-23-4) + benzoyl chloride (98-88-4) → 1,2,3,4,6-penta-O-benzoyl-α-D-galactopyranoside (2592-58-7,3006-48-2,3006-49-3,13526-09-5,14679-57-3,22415-91-4,29884-70-6,41545-55-5,41545-56-6,41569-33-9,96996-90-6,121570-85-2,121570-86-3)

Guidance literature:

D-Galactose; With pyridine; for 0.5h; Molecular sieve; Inert atmosphere;

benzoyl chloride; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1016/j.carres.2013.06.019

Reference yield: 99.5%

D-Galactose (10257-28-0) + benzoyl chloride (98-88-4) → 1,2,3,4,6-Penta-O-benzoyl-α-D-galactopyranose (2592-58-7,3006-48-2,3006-49-3,13526-09-5,14679-57-3,22415-91-4,29884-70-6,41545-55-5,41545-56-6,41569-33-9,96996-90-6,121570-85-2,121570-86-3)

Guidance literature:

With pyridine; In dichloromethane; at 0 - 20 ℃; for 16h; Inert atmosphere;

DOI:10.1080/10286020.2012.670220

upstream raw materials:

D-Mannose

benzoyl chloride

D-Mannose

benzoic acid anhydride

Downstream raw materials:

2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl chloride

2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl bromide

2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl iodide

1,1-bis-benzoylamino-1-deoxy-D-mannitol

Refernces

• 1、 Zhang, Wei,Wang, He-Ying,Wang, Huai-Xu,Zhu, Zhen-Yuan. "Synthesis and inhibition of α-glucosidase of methyl glycyrrhetinate glycosides". supporting information. p. 1874 - 1880. Retrieved 2019/07/22.
• 2、 -. "N-aryl sulfanilamide-N-beta-D-glucopyranose diamide compound and application thereof". Paragraph 0029-0030. . Retrieved 2021/06/26.