[(2S,3R)-3-Methyl-3-acetyloxiranyl]2-O,3-O,4-O,6-O-tetraacetyl-beta-D-glucopyranoside

Base Information

• Chemical Name: [(2S,3R)-3-Methyl-3-acetyloxiranyl]2-O,3-O,4-O,6-O-tetraacetyl-beta-D-glucopyranoside
• CAS No.: 199481-19-1
• Molecular Formula: C₁₉H₂₆O₁₂
• Molecular Weight: 446.408
• DSSTox Substance ID: DTXSID101122145
• Nikkaji Number: J911.341J
• Mol file: 199481-19-1.mol

Synonyms:DTXSID101122145;[(2S,3R)-3-Methyl-3-acetyloxiranyl]2-O,3-O,4-O,6-O-tetraacetyl-beta-D-glucopyranoside;199481-19-1;Ethanone, 1-[(2R,3S)-2-methyl-3-[(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)oxy]oxiranyl]-

Chemical Property of [(2S,3R)-3-Methyl-3-acetyloxiranyl]2-O,3-O,4-O,6-O-tetraacetyl-beta-D-glucopyranoside

Chemical Property:

• XLogP3: -0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 12
• Exact Mass: 446.14242626
• Heavy Atom Count: 31
• Complexity: 748

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)C1(C(O1)OC2C(C(C(C(O2)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)C
• Isomeric SMILES: CC(=O)[C@]1([C@@H](O1)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)C

Technology Process of [(2S,3R)-3-Methyl-3-acetyloxiranyl]2-O,3-O,4-O,6-O-tetraacetyl-beta-D-glucopyranoside

There total 1 articles about [(2S,3R)-3-Methyl-3-acetyloxiranyl]2-O,3-O,4-O,6-O-tetraacetyl-beta-D-glucopyranoside 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: 73.0%

(E)-3-methyl-4-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)but-3-en-2-one (122080-17-5) → Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S)-3-acetyl-3-methyl-oxiranyloxy)-tetrahydro-pyran-3-yl ester + Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2S,3R)-3-acetyl-3-methyl-oxiranyloxy)-tetrahydro-pyran-3-yl ester (199481-19-1)

Guidance literature:

With 3,3-dimethyldioxirane; In acetone; Title compound not separated from byproducts;

Reference yield:

Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2S,3R)-3-acetyl-3-methyl-oxiranyloxy)-tetrahydro-pyran-3-yl ester (199481-19-1) → 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) + (R)-2-Hydroxy-2-methyl-3-oxo-butyraldehyde (219907-83-2)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In chloroform;

DOI:10.1016/S0040-4039(98)02011-5

upstream raw materials:

(E)-3-methyl-4-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)but-3-en-2-one

Downstream raw materials:

2,3,4,5-tetra-O-acetyl-D-glucopyranose

(R)-2-Hydroxy-2-methyl-3-oxo-butyraldehyde