[(2R,3R,4S)-3,4,5-triacetyloxy-3,4-dihydro-2H-pyran-2-yl]methyl acetate

Base Information

• Chemical Name: [(2R,3R,4S)-3,4,5-triacetyloxy-3,4-dihydro-2H-pyran-2-yl]methyl acetate
• CAS No.: 3366-47-0
• Molecular Formula: C14H18O9
• Molecular Weight: 330.292
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID00370472
• Nikkaji Number: J46.721I,J464.588J
• Mol file: 3366-47-0.mol

Synonyms:3366-47-0;2,3,4,6-Tetra-O-acetyl-2-hydroxy-D-glucal;3,4,6-TRI-O-ACETYL-2-ACETOXY-D-GLUCAL;[(2R,3R,4S)-3,4,5-triacetyloxy-3,4-dihydro-2H-pyran-2-yl]methyl acetate;(2R,3R,4S)-2-(Acetoxymethyl)-3,4-dihydro-2H-pyran-3,4,5-triyl triacetate;2,3,4,6-Tetra-O-acetyl-1-deoxy-D-arabino-hex-1-enopyranose;ST50307551;D-Arabino-Hex-1-enitol, 1,5-anhydro-, tetraacetate;D-Arabino-Hex-1-enopyranose, 1-deoxy-, tetraacetate;SCHEMBL6283291;DTXSID00370472;2,3,4,5-Tetra-O-acetyl-1-Deoxy-d-arabino-hex-1-enopyranose,;1-Deoxy-D-arabino-1-hexenopyranose tetraacetate;1,5-Anhydro-D-arabino-hexa-1-enitol tetraacetate;W-202380;2,3,4,5-Tetra-O-acetyl-1-Deoxy-d-arabino-hex-1-enopyranose

Chemical Property of [(2R,3R,4S)-3,4,5-triacetyloxy-3,4-dihydro-2H-pyran-2-yl]methyl acetate

Chemical Property:

• Appearance/Colour: White Solid
• Vapor Pressure: 7.59E-06mmHg at 25°C
• Melting Point: 60℃
• Refractive Index: 1.489
• Boiling Point: 375.777 °C at 760 mmHg
• Flash Point: 162.657 °C
• PSA: 114.43000
• Density: 1.297 g/cm³
• LogP: 0.21620
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Dichloromethane, Methanol (Slightly)
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 9
• Exact Mass: 330.09508215
• Heavy Atom Count: 23
• Complexity: 522

Purity/Quality:

98%min ^*data from raw suppliers

2,3,4,6-Tetra-O-acetyl-2-hydroxy-D-glucal ^*data from reagent suppliers

Safty Information:

• Safety Statements: S24/25:Avoid contact with skin and eyes.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(=CO1)OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H](C(=CO1)OC(=O)C)OC(=O)C)OC(=O)C

Technology Process of [(2R,3R,4S)-3,4,5-triacetyloxy-3,4-dihydro-2H-pyran-2-yl]methyl acetate

There total 16 articles about [(2R,3R,4S)-3,4,5-triacetyloxy-3,4-dihydro-2H-pyran-2-yl]methyl acetate 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: 56.0%

1-methoxy-4-(3,3,3-trifluoroprop-1-en-2-yl)benzene (69843-08-9) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → (2R,3R,4R,5S,6R)-2-(acetoxymethyl)-6-(3,3-difluoro-2-(4-methoxyphenyl)allyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate + 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-arabinohex-1-enopyranose (3366-47-0)

Guidance literature:

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; triethylamine; In acetonitrile; at 25 ℃; for 12h; Reagent/catalyst; Inert atmosphere; Sealed tube; Irradiation;

DOI:10.1021/acs.orglett.1c03390

Reference yield: 47.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (6919-96-6) → 4-nitrophenyl 2,3,4,6-tetra-O-acetyl-D-glucopyranoside (30902-95-5) + 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-arabinohex-1-enopyranose (3366-47-0)

Guidance literature:

4-nitro-phenol; With C₁₆H₂₈AgN₄⁽¹⁺⁾; N-benzyl-N,N,N-triethylammonium chloride; at 25 ℃; for 0.333333h;

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide; at 25 ℃; for 3h;

DOI:10.1016/j.carres.2011.03.007

Reference yield: 37.0%

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl iodide (13035-49-9,14227-51-1,74638-65-6,75788-42-0,75801-94-4) → 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) + 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-arabinohex-1-enopyranose (3366-47-0)

Guidance literature:

With cobalt(III) acetylacetonate; N,N,N,N,-tetramethylethylenediamine; water; phenylmagnesium bromide; In tetrahydrofuran; at 0 - 25 ℃; for 97h; Inert atmosphere;

DOI:10.1016/j.tetlet.2020.152173

upstream raw materials:

nicotinamide

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

per-O-acetyl-α-D-mannopyranose

β-D-glucose pentaacetate

Downstream raw materials:

(S)-6-acetoxymethyl-dihydro-pyran-3,4-dione-bis-phenylhydrazone

2,3,4-tri-O-benzyl-6-deoxy-D-glucopyranose

ethyl 2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside

Refernces

HClO₄?SiO₂ catalysed synthesis of alkyl 3-deoxy-hex-2-enopyranosides from 2-hydroxy glucal ester: Application in the synthesis of a cis-fused bicyclic ether and a 4-amino-C-glucoside

10.1039/b810654a

The research focuses on the development of an efficient method for the synthesis of alkyl 3-deoxy-hex-2-enopyranosides from 2-hydroxy glucal ester using HClO4·SiO2 as a catalyst. This method is highlighted for its high yields, short reaction times, and good a-selectivity. The study explores the reaction of 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-arabino-hex-1-enopyranose with various alcohols, phenols, and thiols, resulting in the formation of corresponding alkyl 3-deoxy-hex-2-enopyranosides. The methodology was also extended to the synthesis of a cis-fused bicyclic ether and a 4-amino-C-glucoside, which are important intermediates in organic synthesis. The experiments involved the use of different reactants, including primary, secondary, and tertiary alcohols, allylic alcohols, phenols, and thiols, with analyses performed using techniques such as NMR, IR, and mass spectrometry to characterize the products. The work-up process was straightforward, involving filtration and chromatographic purification.