(2R,6S)-(+)-4-Benzoyloxy-2-benzoyloxymethyl-6-methoxy-2H-pyran-3(6H)-one

Base Information

• Chemical Name: (2R,6S)-(+)-4-Benzoyloxy-2-benzoyloxymethyl-6-methoxy-2H-pyran-3(6H)-one
• CAS No.: 25552-06-1
• Molecular Formula: C21H18 O7
• Molecular Weight: 382.36
• European Community (EC) Number: 675-683-7
• DSSTox Substance ID: DTXSID70455604
• Wikidata: Q76416663
• Mol file: 25552-06-1.mol

Synonyms:25552-06-1;(2R,6S)-(+)-4-Benzoyloxy-2-benzoyloxymethyl-6-methoxy-2H-pyran-3(6H)-one;[(2S,6R)-4-benzoyloxy-2-methoxy-5-oxo-2H-pyran-6-yl]methyl benzoate;((2R,6S)-4-(Benzoyloxy)-6-methoxy-3-oxo-3,6-dihydro-2H-pyran-2-yl)methyl benzoate;[(2R,6S)-4-(Benzoyloxy)-6-methoxy-3-oxo-3,6-dihydro-2H-pyran-2-yl]methyl benzoate;ETHYL2-BENZYLACETOACETATE;DTXSID70455604;2H-Pyran-3(6H)-one, 4-(benzoyloxy)-2-[(benzoyloxy)methyl]-6-methoxy-, (2R,6S)-

Chemical Property of (2R,6S)-(+)-4-Benzoyloxy-2-benzoyloxymethyl-6-methoxy-2H-pyran-3(6H)-one

Chemical Property:

• Boiling Point: 558.8±50.0 °C(Predicted)
• PSA: 88.13000
• Density: 1.32±0.1 g/cm3(Predicted)
• LogP: 2.52470
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 382.10525291
• Heavy Atom Count: 28
• Complexity: 600

Purity/Quality:

97% ^*data from raw suppliers

(2R,6S)-(+)-4-Benzoyloxy-2-benzoyloxymethyl-6-methoxy- 2H-pyran-3(6H)-one for synthesis ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C=C(C(=O)C(O1)COC(=O)C2=CC=CC=C2)OC(=O)C3=CC=CC=C3
• Isomeric SMILES: CO[C@@H]1C=C(C(=O)[C@H](O1)COC(=O)C2=CC=CC=C2)OC(=O)C3=CC=CC=C3

Technology Process of (2R,6S)-(+)-4-Benzoyloxy-2-benzoyloxymethyl-6-methoxy-2H-pyran-3(6H)-one

There total 2 articles about (2R,6S)-(+)-4-Benzoyloxy-2-benzoyloxymethyl-6-methoxy-2H-pyran-3(6H)-one 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: 75.0%

(E)-4-styrylbenzyl acetate (1081852-38-1) → ((2R,6S)-4-(benzoyloxy)-6-methoxy-3-oxo-3,6-dihydro-2H-pyran-2-yl)methyl benzoate (25552-06-1) + (-)-trans-2-acetoxymethyl-3-phenyloxirane + acetic acid 2,3-epoxy-3-phenyl-propyl ester

Guidance literature:

With Na₂EDTA; oxone; methyl 2,3,6-tri-O-benzoyl-α-D-lyxo-hexapyranoside-4-ulose; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; In water; acetonitrile; at 28 ℃; for 22h; pH=7 - 8; optical yield given as %ee;

DOI:10.1002/adsc.201100735

Reference yield:

→ ((2R,6S)-4-(benzoyloxy)-6-methoxy-3-oxo-3,6-dihydro-2H-pyran-2-yl)methyl benzoate (25552-06-1)

Guidance literature:

aus 3 mit Ac2O in DMSO;

Reference yield: 86.0%

((2R,6S)-4-(benzoyloxy)-6-methoxy-3-oxo-3,6-dihydro-2H-pyran-2-yl)methyl benzoate (25552-06-1) + N-(3,7-dimethyloct-6-enyl)hydroxylamine (129192-82-1) → methyl 3,6-di-O-benzoyl-2-deoxy-2-(N-hydroxy-N-3,7-dimethyloct-6-enylamino)-α-D-arabino-hexopyranosid-4-ulose (129192-81-0)

Guidance literature:

In tetrahydrofuran; at 25 ℃; for 2h;

DOI:10.1016/0008-6215(90)84212-D

upstream raw materials:

(E)-4-styrylbenzyl acetate

Downstream raw materials:

methyl 3,6-di-O-benzoyl-2-deoxy-2-(N-hydroxy-N-methylamino)-α-D-arabino-hexopyranosid-4-ulose

methyl 3,6-di-O-benzoyl-2-deoxy-2-(N-hydroxy-N-3,7-dimethyloct-6-enylamino)-α-D-arabino-hexopyranosid-4-ulose

methyl 3,6-di-O-benzoyl-2-deoxy-2-(N-hydroxy-N-phenylamino)-α-D-arabino-hexopyranosid-4-ulose

methyl 3,6-di-O-benzoyl-2-deoxy-2-(N-benzyl-N-hydroxyamino)-α-D-arabino-hexopyranosid-4-ulose