Levoglucosan, triacetate

Base Information

• Chemical Name: Levoglucosan, triacetate
• CAS No.: 13242-55-2
• Molecular Formula: C12H16O8
• Molecular Weight: 288.254
• Hs Code.: 29400090
• European Community (EC) Number: 236-222-1
• NSC Number: 25284
• Mol file: 13242-55-2.mol

Synonyms:Levoglucosan, triacetate;1,6-Anhydro-beta-D-galactopyranoseTriacetate;13242-55-2;Triacetyllevoglucosan;Idosan triacetate;.beta.-D-Glucopyranose, 1,6-anhydro-, triacetate;EINECS 236-222-1;1,6-Anhydro-beta-D-glucose triacetate;1,6-Anhydro-.beta.-D-glucopyranose triacetate;SCHEMBL7924602;BAKQMOSGYGQJOJ-UHFFFAOYSA-N;NSC25284;NSC 25284;NSC-25284;STK762568;AKOS001740978;NCGC00336232-01;FT-0606989;FT-0662197;.beta.-D-Glucopyranose,6-anhydro-, triacetate;AB01329892-02;beta-D-Glucopyranose, 1,6-anhydro-, triacetate;SR-01000529117;SR-01000529117-1;2,4-BIS(ACETYLOXY)-6,8-DIOXABICYCLO[3.2.1]OCTAN-3-YL ACETATE;6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate (non-preferred name)

Chemical Property of Levoglucosan, triacetate

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 111-112 °C
• Refractive Index: 1.494
• Boiling Point: 392 °C at 760 mmHg
• Flash Point: 147.3 °C
• PSA: 97.36000
• Density: 1.34 g/cm³
• LogP: -0.46340
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform, DMSO, Methanol
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 288.08451746
• Heavy Atom Count: 20
• Complexity: 420

Purity/Quality:

98%min ^*data from raw suppliers

1,6-Anhydro-b-D-glucopyranose, 2,3,4-triacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1C2COC(O2)C(C1OC(=O)C)OC(=O)C
• Uses: 1,6-Anhydrohexopyranoses have proven to be valuable synthons for the preparation of biologically important and structurally diverse products (e.g. rifamycin S, indanomycin, thromboxane B2, (+)-biotin, tetrodotoxin, quinone, and macrolide antibiotics) as well as for modified sugars.

Technology Process of Levoglucosan, triacetate

There total 48 articles about Levoglucosan, triacetate 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%

acetic anhydride (108-24-7) + levoglucosan (498-07-7) → 2,3,4-tri-O-acetyllevoglucosan (13242-55-2,33360-71-3)

Guidance literature:

scandium tris(trifluoromethanesulfonate); at 20 ℃; for 0.2h;

DOI:10.1016/S0040-4039(01)02253-5

Reference yield: 95.0%

1,2,3,4-tetra-O-acetyl-6-O-trityl-β-D-glucopyranose (37074-90-1) → 2,3,4-tri-O-acetyllevoglucosan (13242-55-2,33360-71-3)

Guidance literature:

With tin(IV) chloride; In 1,2-dichloro-ethane; at 25 ℃; for 12h; Product distribution; variation of Lewis acids;

DOI:10.1016/0008-6215(87)80208-2

Reference yield: 80.0%

acetic anhydride (108-24-7) + 1,2,3,4-tetra-O-acetyl-6-O-p-tolylsulfonyl-α,β-D-glucopyranose (95118-61-9) → 2,3,4-tri-O-acetyllevoglucosan (13242-55-2,33360-71-3)

Guidance literature:

1,2,3,4-tetra-O-acetyl-6-O-p-tolylsulfonyl-α,β-D-glucopyranose; With aluminum oxide; at 110 ℃; for 0.116667h; microwave irradiation;

acetic anhydride; With potassium acetate; at 100 ℃; for 0.333333h;

DOI:10.1055/s-2003-39168

upstream raw materials:

1,2,3,4-tetra-O-acetyl-6-O-trityl-β-D-glucopyranose

1-methyl-4-nitrosobenzene

Brigl's anhydride

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

Downstream raw materials:

(6S)-tri-O-acetyl-1,6-anhydro-6-methoxy-β-D-glucopyranose

methyl (methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate

(6S)-2,3,4,-tri-O-acetyl-1,6-anhydro-6-bromo-β-D-glucopyranose

1,6-anhydro-2,4-di-O-acetyl-β-D-glucopyranose

Refernces

• 1、 Skorupowa,Dmochowska,Madaj,Kasprzykowski,Sokolowski,Wisniewski. "Cyclization of N-(Tetra-O-acetyl-D-gluco- and D-mannopyranosyl)-pyridinium salts in a methanolic solution of sodium methylate". . p. 49 - 59. Retrieved 1998.
• 2、 Zottola, Mark A.,Alonso, Ricardo,Vite, Gregory D.,Fraser-Reid, Bert. "A Practical, Efficient Large-Scale Synthesis of 1,6-Anhydrohexopyranoses". . p. 6123 - 6125. Retrieved 1989.
• 3、 Chan, Jefferson,Tang, Ariel,Bennet, Andrew J.. "A stepwise solvent-promoted SNi reaction of α-d- glucopyranosyl fluoride: Mechanistic implications for retaining glycosyltransferases". . p. 1212 - 1220. Retrieved 2012.
• 4、 Coleman et al.. "-". . p. 1040. Retrieved 1944.
• 5、 Rao, Mothe Vaman,Nagarajan, Madhavarao. "An improved synthesis of 2,3,4-tri-O-acetyl-1,6-anhydro-β-D-glucopyranose (levoglucosan triacetate)". . p. 141 - 144. Retrieved 1987.
• 6、 Budesinsky, Milos,Polakova, Jana,Hamernikova, Michaela,Cisarova, Ivana,Trnka, Tomas,Cerny, Miloslav. "1,6-Anhydro-1-thio-β-D-glucopyranose (thiolevoglucosan) and the corresponding sulfoxides and sulfone". . p. 311 - 336. Retrieved 2007/10/03.