1,5-Dianhydro-2,6-dideoxy-L-arabino-hex-1-enitol diacetate

Base Information

• Chemical Name: 1,5-Dianhydro-2,6-dideoxy-L-arabino-hex-1-enitol diacetate
• CAS No.: 34819-86-8
• Molecular Formula: C10H14 O5
• Molecular Weight: 214.218
• Hs Code.: 29400090
• European Community (EC) Number: 252-228-7
• NSC Number: 185346,101759
• DSSTox Substance ID: DTXSID80956298
• Mol file: 34819-86-8.mol

Synonyms:(3-acetyloxy-2-methyl-3,4-dihydro-2H-pyran-4-yl) acetate;1,5-Dianhydro-2,6-dideoxy-L-arabino-hex-1-enitol diacetate;2-Methyl-3,4-dihydro-2H-pyran-3,4-diyl diacetate;NSC185346;3,4-di-o-acetyl-2,6-anhydro-1,5-dideoxyhex-5-enitol;SCHEMBL21843000;DTXSID80956298;HMS3354L16;BCP32017;EINECS 252-228-7;NSC101759;AKOS030212693;NSC-101759;NSC-185346;PD130999;FT-0666467;3,4-Di-O-acetyl-6-deoxy-L-glucal;3,4-Di-O-acetyl-1,5-anhydro-2,6-dideoxy-L-arabino-hex-1-enitol

Chemical Property of 1,5-Dianhydro-2,6-dideoxy-L-arabino-hex-1-enitol diacetate

Chemical Property:

• Appearance/Colour: pale yellow
• Vapor Pressure: 0.00149mmHg at 25°C
• Refractive Index: n20/D 1.454(lit.)
• Boiling Point: 68-69 °C0.06 mm Hg(lit.)
• Flash Point: >230 °F
• PSA: 61.83000
• Density: 1.116 g/mL at 25 °C(lit.)
• LogP: 0.78220
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Dichloromethane
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 214.08412354
• Heavy Atom Count: 15
• Complexity: 284

Purity/Quality:

98%, ^*data from raw suppliers

3,4-Di-O-acetyl-L-rhamnal ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1C(C(C=CO1)OC(=O)C)OC(=O)C
• Uses: A DNA-binding agent.

Technology Process of 1,5-Dianhydro-2,6-dideoxy-L-arabino-hex-1-enitol diacetate

There total 34 articles about 1,5-Dianhydro-2,6-dideoxy-L-arabino-hex-1-enitol diacetate 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: 95.0%

L-Rhamnose (3615-41-6,478518-52-4) + acetic anhydride (108-24-7) → 3,4-di-O-acetyl-6-deoxy-L-glucal (34819-86-8)

Guidance literature:

L-Rhamnose; acetic anhydride; With perchloric acid; at 40 ℃; for 1.5h; Inert atmosphere;

With hydrogen bromide; acetic acid; at 23 ℃; for 5h; Inert atmosphere;

With zinc; In tetrahydrofuran; at -20 - 0 ℃; for 2h; Inert atmosphere;

DOI:10.1039/c1cc11448d

Reference yield: 93.0%

2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl bromide (5158-64-5) → 3,4-di-O-acetyl-6-deoxy-L-glucal (34819-86-8)

Guidance literature:

With zinc; sodium acetate; acetic acid; In tetrahydrofuran; at 20 ℃; for 2.5h;

DOI:10.1039/c4ra08028a

Reference yield: 85.0%

L-rhamnose (73-34-7) + acetic anhydride (108-24-7) → 3,4-di-O-acetyl-6-deoxy-L-glucal (34819-86-8)

Guidance literature:

L-rhamnose; acetic anhydride; With hydrogen bromide; In acetic acid; for 8h;

With sodium acetate; copper(II) sulfate; zinc; In water; acetic acid; for 1.5h; Further stages.;

DOI:10.1016/j.carres.2007.09.012

upstream raw materials:

2,3,4-tri-O-acetyl-6-deoxy-beta-L-mannopyranosyl bromide

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

Acetic acid (2S,3S,4S)-3-acetoxy-2-methyl-6-(pyridin-2-ylsulfanyl)-tetrahydro-pyran-4-yl ester

Methyl 6-O-Benzoyl-2,3-di-O-benzyl-α-D-glucopyranoside

Downstream raw materials:

L-rhamnal

Acetic acid (2S,3R,6S)-2-methyl-6-(2-methyl-cyclohex-2-enyl)-3,6-dihydro-2H-pyran-3-yl ester

Acetic acid (2S,3R,6R)-2-methyl-6-(2-methyl-cyclohex-2-enyl)-3,6-dihydro-2H-pyran-3-yl ester

(6S)-(6-methyltetrahydropyran-2-yl)acetophenone

Refernces

• 1、 Iselin,Reichstein. "-". . p. 1146,1148. Retrieved 1944.
• 2、 Karki, Geeta,Kumar, Harikesh,Rajan, Remya,Mandal, Pintu Kumar. "Expeditious Synthesis of a Tetrasaccharide Repeating Unit of the O-Antigen of Escherichia coli O163". . p. 2581 - 2586. Retrieved 2016.
• 3、 Bennett, Clay S.,DeYong, Ashley E.,Florek, John,Nguyen, Tu-Anh,Pohl, Nicola L. B.,Stamper, Gavin,Vasquez, Olivea,Yalamanchili, Subbarao,Zsikla, Alexander. "Automated, Multistep Continuous-Flow Synthesis of 2,6-Dideoxy and 3-Amino-2,3,6-trideoxy Monosaccharide Building Blocks". supporting information. p. 23171 - 23175. Retrieved 2021/09/25.
• 4、 -. "Preparation method and application of first-class rhamnose C-glycoside". Paragraph 0030; 0035-0036. . Retrieved 2020/03/11.