Acetic acid 4,5-diacetoxy-6-acetoxymethyl-2-bromo-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid 4,5-diacetoxy-6-acetoxymethyl-2-bromo-tetrahydro-pyran-3-yl ester
• CAS No.: 3068-32-4
• Molecular Formula: C14H19BrO9
• Molecular Weight: 411.203
• Hs Code.: 29329990
• DSSTox Substance ID: DTXSID70862218
• Mol file: 3068-32-4.mol

Synonyms:2,3,4,6-tetra-o-acetyl-alpha-galactosylpyranosyl bromide;529493-92-3;Acetic acid 4,5-diacetoxy-6-acetoxymethyl-2-bromo-tetrahydro-pyran-3-yl ester;(3,4,5-triacetyloxy-6-bromooxan-2-yl)methyl acetate;2,3,4,6-tetra-o-acetyl-alpha-D-glucosylpyranosyl bromide;2-(acetoxymethyl)-6-bromotetrahydro-2H-pyran-3,4,5-triyl triacetate;[(2R,3R,4S,5R,6S)-3,4,5-triacetoxy-6-bromo-tetrahydropyran-2-yl]methyl acetate;Tetra-O-acetyl-alpha-D-galactopyranosyl bromide;ACETOBROMOGALACTOSE;MFCD00063254;MFCD00063686;Tetra-O-acetyl-alpha-D-mannosyl bromide;EINECS 221-324-0;2,3,4,6-tetra-o-acetyl-alpha-d-glucopyranosyl;Acetobromo-?-D-glucose;alpha-D-Galactopyranosyl bromide, tetraacetate;SCHEMBL152577;DTXSID70862218;BCP29620;BCP31752;BCP34473;AKOS015896823;AC-1401;SB74160;BP-22359;BP-22518;SY029051;SY059513;HY-141137;CS-0116028;FT-0621793;FT-0623211;FT-0663875;FT-0696087;tetra-O-acetyl-|A-D-galactopyranosyl bromide;2,3,4,6-Tetra-O-acetylhexopyranosyl bromide;.alpha.-D-Glucopyranosyl bromide, tetraacetate;2,3,4,6-Tetra-O-acetylhexopyranosyl bromide #;F0001-0939;[3,4,5-tris(acetyloxy)-6-bromooxan-2-yl]methyl acetate;3,4,5-triacetoxy-6-bromo-tetrahydropyran-2-ylmethyl actate;3,4,5-triacetoxy-6-bromo-tetrahydropyran-2-ylmethyl acetate;4,5-diacetoxy-6-acetoxymethyl-2-bromo-tetrahydro-pyran-3-yl acetate;4,5-diacetoxy-6-acetoxymethyl-2-bromotetrahydropyran-3-yl acetate;acetobromo-?-d-galactose;Acetobromomannose;Bromo 2,3,4,6-Tetra-O-acetyl-alpha-D-mannopyranoside;Acetobromglucose;Acetobromo-alpha-D-glucose;Acetobromo-(c) paragraph sign-D-glucose;Bromo 2,3,4,6-Tetra-O-acetyl-alpha-D-galactopyranoside(Stabilized with 2per cent (wt/wt) CaCO3)

Chemical Property of Acetic acid 4,5-diacetoxy-6-acetoxymethyl-2-bromo-tetrahydro-pyran-3-yl ester

Chemical Property:

• Appearance/Colour: White crystalline solid
• Vapor Pressure: 5.35E-07mmHg at 25°C
• Melting Point: 83-85 °C
• Refractive Index: 1.503
• Boiling Point: 412 °C at 760 mmHg
• Flash Point: 203 °C
• PSA: 114.43000
• Density: 1.49 g/cm³
• LogP: 0.46440
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly), Water (Sli
• Water Solubility.: Sparingly soluble
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 9
• Exact Mass: 410.02124
• Heavy Atom Count: 24
• Complexity: 507

Purity/Quality:

98% ^*data from raw suppliers

Bromo 2,3,4,6-Tetra-O-acetyl-a-D-galactopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)Br)OC(=O)C)OC(=O)C)OC(=O)C
• Uses: Temperature and moisture sensitive; Store in freezer; Stabilized with 2% CaCO3

Technology Process of Acetic acid 4,5-diacetoxy-6-acetoxymethyl-2-bromo-tetrahydro-pyran-3-yl ester

There total 77 articles about Acetic acid 4,5-diacetoxy-6-acetoxymethyl-2-bromo-tetrahydro-pyran-3-yl ester 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: 100.0%

β-D-galactose peracetate (4163-60-4) → 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4)

Guidance literature:

With hydrogen bromide; acetic acid; at 0 - 20 ℃;

DOI:10.1055/s-0029-1218818

Reference yield: 100.0%

D-galactose pentaacetate (25878-60-8) → 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4)

Guidance literature:

With hydrogen bromide; acetic acid; at 0 - 10 ℃;

DOI:10.1039/c2ob25207d

Reference yield: 100.0%

D-Galactose (59-23-4) + acetic acid (64-19-7,77671-22-8) → 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4)

Guidance literature:

With Acetyl bromide; at 20 ℃;

DOI:10.1016/j.tetasy.2009.02.038

upstream raw materials:

D-Galactose

acetic anhydride

β-D-galactose peracetate

2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose

Downstream raw materials:

3-β-D-galactopyranosyloxy-4-β-D-glucopyranosyloxy-benzaldehyde

cyclohexyl-(1-thio-β-D-galactopyranoside)

4-nitrophenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

p-nitrophenyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside

Refernces

• 1、 Torgov, Vladimir,Danilov, Leonid,Utkina, Natalia,Veselovsky, Vladimir,Brockhausen, Inka. "Synthesis of P1-(11-phenoxyundecyl)-P2-(2-acetamido-2-deoxy-3-O-α-D-rhamnopyranosyl-α-D-glucopyranosyl) diphosphate and P1-(11-phenoxyundecyl)-P2-(2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranosyl) diphosphate for the investigation of biosynthesis of O-antigenic polysaccharides in Pseudomonas aeruginosa and Escherichia coli O104". . p. 19 - 25. Retrieved 2017.
• 2、 Andreana, Peter R.,Xie, Wenhua,Cheng, Huai N.,Qiao, Lei,Murphy, Dennis J.,Gu, Qu-Ming,Wang, Peng G.. "In Situ Preparation of β-D-1-O-Hydroxylamino Carbohydrate Polymers Mediated by Galactose Oxidase". . p. 1863 - 1866. Retrieved 2002.
• 3、 Malkar, Navdeep B.,Lauer-Fields, Janelle L.,Fields, Gregg B.. "Convenient synthesis of glycosylated hydroxylysine derivatives for use in solid-phase peptide synthesis". . p. 1137 - 1140. Retrieved 2000.
• 4、 Bradley, Helena,Fitzpatrick, Geraldine,Glass, W. Kenneth,Kunz, Horst,Murphy, Paul V.. "Application of Ugi reactions in synthesis of divalent neoglycoconjugates: Evidence that the sugars are presented in restricted conformation". . p. 2629 - 2632. Retrieved 2001.
• 5、 Ahmed, Ajaz,Bhagat, Kavita,Choudhary, Sushil,Kaur Gulati, Harmandeep,Kumar, Ajay,Kumar, Nitish,Mukherjee, Debaraj,Singh Bedi, Preet Mohinder,Singh, Atamjit,Singh, Harbinder,Vir Singh, Jatinder. "Design, Synthesis, biological investigations and molecular interactions of triazole linked tacrine glycoconjugates as Acetylcholinesterase inhibitors with reduced hepatotoxicity". . . Retrieved 2021/11/23.
• 6、 St-Gelais, Jacob,Leclerc, Christina,Giguère, Denis. "Synthesis of fluorinated thiodigalactoside analogues". . . Retrieved 2021/11/30.