((2R,3S,4R)-4-(Benzoyloxy)-3-hydroxy-3,4-dihydro-2H-pyran-2-yl)methyl benzoate

Base Information

• Chemical Name: ((2R,3S,4R)-4-(Benzoyloxy)-3-hydroxy-3,4-dihydro-2H-pyran-2-yl)methyl benzoate
• CAS No.: 58871-06-0
• Molecular Formula: C20H18O6
• Molecular Weight: 388.37
• Hs Code.: 2932999099
• Nikkaji Number: J1.516.323B
• Mol file: 58871-06-0.mol

Synonyms:58871-06-0;((2R,3S,4R)-4-(Benzoyloxy)-3-hydroxy-3,4-dihydro-2H-pyran-2-yl)methyl benzoate;SCHEMBL9186081;[(2R,3S,4R)-4-benzoyloxy-3-hydroxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate;[(2R,3R,4S,5R)-4-benzoyloxy-2,3,5-trihydroxy-6-oxohexyl] benzoate;AKOS015889151;CID 10861153;CS-0454028;V10109;A914247;((2R,3S,4R)-4-(Benzoyloxy)-3-hydroxy-3,4-dihydro-2H-pyran-2-yl)methylbenzoate;4alpha-(Benzoyloxy)-2alpha-(benzoyloxymethyl)-3,4-dihydro-2H-pyran-3beta-ol

Chemical Property of ((2R,3S,4R)-4-(Benzoyloxy)-3-hydroxy-3,4-dihydro-2H-pyran-2-yl)methyl benzoate

Chemical Property:

• Melting Point: 129-134 °C(lit.)
• PSA: 130.36000
• LogP: 0.35060
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 354.11033829
• Heavy Atom Count: 26
• Complexity: 504

Purity/Quality:

99%min ^*data from raw suppliers

3,6-Di-O-benzoyl-D-glucal Aldrich ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)OCC2C(C(C=CO2)OC(=O)C3=CC=CC=C3)O
• Isomeric SMILES: C1=CC=C(C=C1)C(=O)OC[C@@H]2[C@H]([C@@H](C=CO2)OC(=O)C3=CC=CC=C3)O

Technology Process of ((2R,3S,4R)-4-(Benzoyloxy)-3-hydroxy-3,4-dihydro-2H-pyran-2-yl)methyl benzoate

There total 5 articles about ((2R,3S,4R)-4-(Benzoyloxy)-3-hydroxy-3,4-dihydro-2H-pyran-2-yl)methyl benzoate 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: 91.0%

1,5-anhydro-3,4-di-O-benzoyl-6-O-t-butyldimethylsilyl-2-deoxy-D-arabino-hex-1-enitol (136573-59-6) → 1,5-anhydro-3,6-di-O-benzoyl-2-deoxy-D-arabino-hex-1-enitol (58871-06-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 15h;

DOI:10.1002/chem.200701288

Reference yield: 80.0%

C29H38O6Si → 1,5-anhydro-3,6-di-O-benzoyl-2-deoxy-D-arabino-hex-1-enitol (58871-06-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/S0040-4039(01)00611-6

Reference yield: 56.0%

benzoyl chloride (98-88-4) + D-glucal (13265-84-4) → 1,5-anhydro-3,6-di-O-benzoyl-2-deoxy-D-arabino-hex-1-enitol (58871-06-0)

Guidance literature:

With pyridine;

DOI:10.1016/S0008-6215(00)81000-9

upstream raw materials:

benzoyl chloride

D-glucal

1,5-anhydro-3,4-di-O-benzoyl-6-O-t-butyldimethylsilyl-2-deoxy-D-arabino-hex-1-enitol

Downstream raw materials:

4-azido-4-deoxy-3,6-di-O-benzoyl-D-galactal

(2R,3S,4R)-3-sulfamoyloxymethyl-3,4-dihydro-2H-pyran-2-benzoyloxymethyl-4-yl-benzoate

methyl 2-deoxy-α-D-galactopyranoside

1,4,6-tri-O-benzoyl-2,3-dideoxy-α-D-threo-hex-2-enopyranose

Refernces

• 1、 Zhong, Ming,Meng, Xiang-Bao,Li, Zhong-Jun. "Synthesis of γ-aminobutyric acid analogs based on carbohydrate scaffolds". scheme or table. p. 1099 - 1106. Retrieved 2010/09/12.
• 2、 Graziani, Andrea,Passacantilli, Pietro,Piancatelli, Giovanni,Tani, Simona. "A mild and efficient approach for the regioselective silyl-mediated protection-deprotection of C-4 hydroxyl group on carbohydrates". . p. 3857 - 3860. Retrieved 2007/10/03.