1,6-Anhydro-2,3,4-tri-O-benzyl-beta-D-glucopyranose

Base Information

• Chemical Name: 1,6-Anhydro-2,3,4-tri-O-benzyl-beta-D-glucopyranose
• CAS No.: 10548-46-6
• Molecular Formula: C27H28O5
• Molecular Weight: 432.516
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID50447047
• Nikkaji Number: J667.501H
• Wikidata: Q82265821
• Mol file: 10548-46-6.mol

Synonyms:10548-46-6;1,6-Anhydro-2,3,4-tri-O-benzyl-beta-D-glucopyranose;Tribenzyllevoglucosan;1,6-Anhydro-2,3,4-tri-O-benzyl-b-D-glucopyranose;(1R,2R,3S,4R,5R)-2,3,4-tris(phenylmethoxy)-6,8-dioxabicyclo[3.2.1]octane;1,6-Anhydro-2,3,4-tri-O-benzyl-|A-D-glucopyranose;SCHEMBL8342076;(1R,2R,3S,4R,5R)-2,3,4-tris(benzyloxy)-6,8-dioxabicyclo[3.2.1]octane;DTXSID50447047;B-D-GLUCOPYRANOSE,1,6-ANHYDRO-2,3,4-TRIS-O-(PHENYLMETHYL)-;MFCD02683260;AKOS030241018;CS-0440305;W-200740;(1R,2R,3S,4R,5R)-2,3,4-Tris(benzyloxy)-6,8-dioxabicyclo[3.2.1]octane (non-preferred name)

Chemical Property of 1,6-Anhydro-2,3,4-tri-O-benzyl-beta-D-glucopyranose

Chemical Property:

• Vapor Pressure: 8E-12mmHg at 25°C
• Melting Point: 81-84°C
• Refractive Index: 1.611
• Boiling Point: 555.8 °C at 760 mmHg
• Flash Point: 220.8 °C
• PSA: 46.15000
• Density: 1.22 g/cm³
• LogP: 4.49770
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform, Ethyl Acetate
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 432.19367399
• Heavy Atom Count: 32
• Complexity: 538

Purity/Quality:

98%,99%, ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C(C(C(C(O1)O2)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5
• Isomeric SMILES: C1[C@@H]2[C@H]([C@@H]([C@H]([C@H](O1)O2)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5
• 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 1,6-Anhydro-2,3,4-tri-O-benzyl-beta-D-glucopyranose

There total 37 articles about 1,6-Anhydro-2,3,4-tri-O-benzyl-beta-D-glucopyranose 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: 93.0%

benzyl bromide (100-39-0) + levoglucosan (498-07-7) → 1,6-anhydro-2,3,4-tri-O-benzyl-β-D-glucopyranose (10548-46-6)

Guidance literature:

levoglucosan; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

benzyl bromide; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1021/jf800326r

Reference yield: 92.0%

benzyl chloride (100-44-7) + levoglucosan (498-07-7) → 1,6-anhydro-2,3,4-tri-O-benzyl-β-D-glucopyranose (10548-46-6)

Guidance literature:

With sodium hydroxide; potassium carbonate; tert-Amyl alcohol; tetra(n-butyl)ammonium hydrogensulfate; In dimethyl sulfoxide; benzene; for 5h; Ambient temperature;

Reference yield: 89.0%

2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl fluoride (78153-79-4) → 1,6-anhydro-2,3,4-tri-O-benzyl-β-D-glucopyranose (10548-46-6)

Guidance literature:

With lithium perchlorate; In diethyl ether; at 25 ℃; for 24h;

upstream raw materials:

benzyl chloride

2,3,4-tri-O-acetyllevoglucosan

thiophene

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate

Downstream raw materials:

[(2R,3R,4R,5S,6R)-3,4,5-tris(benzyloxy)-6-(prop-2-en-1-yl)oxan-2-yl]methanol

1-thio-α,α-trehalose

Refernces

• 1、 Bosco, Michael,Rat, Stéphanie,Dupré, Nathalie,Hasenknopf, Bernold,Lac?te, Emmanuel,Malacria, Max,Rémy, Pauline,Kovensky, Jose,Thorimbert, Serge,Wadouachi, Anne. "Lewis-acidic polyoxometalates as reusable catalysts for the synthesis of glucuronic acid esters under microwave irradiation". . p. 1249 - 1252. Retrieved 2010.
• 2、 Xia, Meng-jie,Yao, Wang,Meng, Xiang-bao,Lou, Qing-hua,Li, Zhong-jun. "Co2(CO)6-propargyl cation mediates glycosylation reaction by using thioglycoside". . p. 2389 - 2392. Retrieved 2017/05/29.
• 3、 Zhu, Xiangming,Dere, Ravindra T.,Jiang, Junyan,Zhang, Lei,Wang, Xiaoxia. "Synthesis of α-glycosyl thiols by stereospecific ring-opening of 1,6-anhydrosugars". experimental part. p. 10187 - 10197. Retrieved 2012/02/05.