3,5-Diacetoxy-2-acetoxymethyl-6-phenethyl-tetrahydro-pyran-4-ylester

Base Information

• Chemical Name: 3,5-Diacetoxy-2-acetoxymethyl-6-phenethyl-tetrahydro-pyran-4-ylester
• CAS No.: 85422-91-9
• Molecular Formula: C22H28 O9
• Molecular Weight: 436.459
• DSSTox Substance ID: DTXSID50705351
• Nikkaji Number: J2.671.873B
• Wikidata: Q82638193
• Mol file: 85422-91-9.mol

Synonyms:85422-91-9;3,5-diacetoxy-2-acetoxymethyl-6-phenethyl-tetrahydro-pyran-4-ylester;[(2R,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-(2-phenylethyl)oxan-2-yl]methyl acetate;DTXSID50705351;1-Phenethyl-2-O,3-O,4-O,6-O-tetraacetyl-1-deoxy-beta-D-glucopyranose;4,5,6,8-Tetra-O-acetyl-3,7-anhydro-1,2-dideoxy-1-phenyl-D-glycero-D-gulo-octitol

Chemical Property of 3,5-Diacetoxy-2-acetoxymethyl-6-phenethyl-tetrahydro-pyran-4-ylester

Chemical Property:

• PSA: 226.33000
• LogP: 0.20990
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 12
• Exact Mass: 436.17333247
• Heavy Atom Count: 31
• Complexity: 641

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)CCC2=CC=CC=C2)OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)CCC2=CC=CC=C2)OC(=O)C)OC(=O)C)OC(=O)C

Technology Process of 3,5-Diacetoxy-2-acetoxymethyl-6-phenethyl-tetrahydro-pyran-4-ylester

There total 6 articles about 3,5-Diacetoxy-2-acetoxymethyl-6-phenethyl-tetrahydro-pyran-4-ylester 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: 85.0%

1-deoxy-1-(C-2',4',6'-trimethoxyphenyl)-2,3,4,6-tetra-O-benzyl-D-glucopyranose → α-1-deoxy-1-(C-1'-phenethyl)-2,3,4,6-tetra-O-acetyl-D-glucopyranose (85422-91-9,114421-40-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; at 25 ℃; for 12h;

DOI:10.1021/ja00300a036

Reference yield: 52.0%

acetic anhydride (108-24-7) + α-1-deoxy-1-(C-1'-phenethyl)-2,3,4,6-tetra-O-acetyl-D-glucopyranose (96689-92-8) → α-1-deoxy-1-(C-1'-phenethyl)-2,3,4,6-tetra-O-acetyl-D-glucopyranose (85422-91-9,114421-40-8)

Guidance literature:

With pyridine; dmap; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1021/ja00300a036

Reference yield:

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 2,3,4,5-tetra-O-acetyl-D-glucopyranose (3947-62-4,6207-76-7,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,10343-06-3) + α-1-deoxy-1-(C-1'-phenethyl)-2,3,4,6-tetra-O-acetyl-D-glucopyranose (85422-91-9,114421-40-8)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; ammonium bromide; 2,6-bis[(4R)-5,5-dihydro-4-phenyl-2-oxazolyl]pyridine; zinc; In N,N-dimethyl acetamide; at 25 ℃; for 12h; Inert atmosphere;

DOI:10.1021/ol8028737

upstream raw materials:

acetic anhydride

α-1-deoxy-1-(C-1'-phenethyl)-2,3,4,6-tetra-O-acetyl-D-glucopyranose

2-(2,3,4,6-Tetra-O-benzyl-α,β-D-glucopyranosyl)acetophenon

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

Refernces

• 1、 Hoffmann, Michael G.,Schmidt, Richard R.. "O-Glycosyl Imidates, 19. - Reactions of Glycosyl Trichloroacetimidates with Silylated C-Nucleophiles". . p. 2403 - 2419. Retrieved 2007/10/02.