3,5,6-tri-O-.benzyl-1,2-O-isopropylidene-alpha-D-glucofuranose

Base Information

• Chemical Name: 3,5,6-tri-O-.benzyl-1,2-O-isopropylidene-alpha-D-glucofuranose
• CAS No.: 53928-30-6
• Molecular Formula: C30H34O6
• Molecular Weight: 490.596
• European Community (EC) Number: 258-868-3
• UNII: J63MA3RV3G
• DSSTox Substance ID: DTXSID30968720
• Nikkaji Number: J279.541H
• Wikidata: Q76009887
• Mol file: 53928-30-6.mol

Synonyms:53928-30-6;1,2-O-ISOPROPYLIDENE-3,5,6-TRI-O-BENZYL-ALPHA-D-GLUCOFURANOSE;3,5,6-tri-O-.benzyl-1,2-O-isopropylidene-alpha-D-glucofuranose;EINECS 258-868-3;J63MA3RV3G;3,5,6-Tri-O-benzyl-1,2-O-isopropylidene-alpha-D-glucofuranose;(3aR,5R,6S,6aR)-5-[(1R)-1,2-bis(phenylmethoxy)ethyl]-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole;EC 258-868-3;(3AR,5R,6S,6aR)-6-(benzyloxy)-5-((R)-1,2-bis(benzyloxy)ethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole;UNII-J63MA3RV3G;SCHEMBL11316974;DTXSID30968720;MFCD08703754;C30-H34-O6;TRIBENOSIDE IMPURITY A [EP IMPURITY];F20548;W-111078;3,5,6-Tri-O-benzyl-1,2-O-isopropylidene-D-glucofuranose;3,5,6-Tri-O-benzyl-1,2-O-(1-methylethylidene)hexofuranose;1,2-O-ISOPROPYLIDENE-3,5,6-TRI-O-BENZYL-.ALPHA.-D-GLUCOFURANOSE;1-O,2-O-Isopropylidene-3-O,5-O,6-O-tribenzyl-alpha-D-glucofuranose;.ALPHA.-D-GLUCOFURANOSE, 1,2-O-(1-METHYLETHYLIDENE)-3,5,6-TRIS-O-(PHENYLMETHYL)-;3,5,6-TRI-O-BENZYL-1,2-O-(1-METHYLETHYLIDENE)-.ALPHA.-D-GLUCOFURANOSE;(3aR,5R,6S,6aR)-6-(benzyloxy)-5-[(1R)-1,2-bis(benzyloxy)ethyl]-2,2-dimethyl-tetrahydro-2H-furo[2,3-d][1,3]dioxole

Chemical Property of 3,5,6-tri-O-.benzyl-1,2-O-isopropylidene-alpha-D-glucofuranose

Chemical Property:

• Vapor Pressure: 2.89E-13mmHg at 25°C
• Boiling Point: 589.7 °C at 760 mmHg
• Flash Point: 228 °C
• PSA: 55.38000
• Density: 1.2 g/cm³
• LogP: 5.25040
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 490.23553880
• Heavy Atom Count: 36
• Complexity: 637

Purity/Quality:

99%, ^*data from raw suppliers

3,5,6-Tri-O-benzyl-1,2-O-Isopropylidene-a-D-glucofuranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C(C(OC2O1)C(COCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5)C
• Isomeric SMILES: CC1(O[C@@H]2[C@H]([C@H](O[C@@H]2O1)[C@@H](COCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5)C
• Uses: 1,2-O-Isopropylidene-3,5,6-tri-O-benzyl-α-D-glucofuranose can be used in cancer treatment as it exhibits antitumor and antiproliferative activity.

Technology Process of 3,5,6-tri-O-.benzyl-1,2-O-isopropylidene-alpha-D-glucofuranose

There total 7 articles about 3,5,6-tri-O-.benzyl-1,2-O-isopropylidene-alpha-D-glucofuranose 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: 97.0%

benzyl bromide (100-39-0) + 1,2-O-isopropylidene-α-D-glucofuranose (18549-40-1) → 1,2-O-isopropylidene-3,5,6-tri-O-benzyl-α-D-glucofuranoside (53928-30-6)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 2.5h;

DOI:10.1016/j.bmcl.2016.05.044

Reference yield: 95.0%

benzyl chloride (100-44-7) + 1,2-O-isopropylidene-α-D-glucofuranose (18549-40-1) → 1,2-O-isopropylidene-3,5,6-tri-O-benzyl-α-D-glucofuranoside (53928-30-6)

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: 37.0%

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol (22529-61-9) + benzyl bromide (100-39-0) → 3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose (28713-39-5) + 1,2-O-isopropylidene-3,6-di-O-benzyl-α-D-glucofuranose (81823-12-3) + 1,2-O-isopropylidene-3,5,6-tri-O-benzyl-α-D-glucofuranoside (53928-30-6)

Guidance literature:

With barium dihydroxide; barium(II) oxide; In N,N-dimethyl-formamide; for 2h; Ambient temperature;

DOI:10.1002/recl.19871061105

upstream raw materials:

benzyl chloride

1,2-O-isopropylidene-α-D-glucofuranose

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

benzyl bromide

Downstream raw materials:

allyl 3,5,6-tri-O-benzyl-α-D-glucofuranoside

Refernces

• 1、 Glenister, Alexandra,Simone, Michela I.,Hambley, Trevor W.. "A Warburg effect targeting vector designed to increase the uptake of compounds by cancer cells demonstrates glucose and hypoxia dependent uptake". . . Retrieved 2019/07/31.
• 2、 Patra, Malay,Awuah, Samuel G.,Lippard, Stephen J.. "Chemical Approach to Positional Isomers of Glucose-Platinum Conjugates Reveals Specific Cancer Targeting through Glucose-Transporter-Mediated Uptake in Vitro and in Vivo". supporting information. p. 12541 - 12551. Retrieved 2016/10/07.