118895-86-6

Basic information

• Product Name: 1,2,3,4,5,6-Hexabenzyloxy-hexane
• Synonyms: 1,2,3,4,5,6-Hexabenzyloxy-hexane
• CAS NO: 118895-86-6
• Molecular Formula: C₄₈H₅₀O₆
• Molecular Weight: 722.907
• Mol File: 118895-86-6.mol

Chemical Properties

• Boiling Point: 788.744°C at 760 mmHg
• Flash Point: 278.363°C
• Appearance: /
• Density: 1.147g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.597
• CAS DataBase Reference: 1,2,3,4,5,6-Hexabenzyloxy-hexane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4,5,6-Hexabenzyloxy-hexane(118895-86-6)
• EPA Substance Registry System: 1,2,3,4,5,6-Hexabenzyloxy-hexane(118895-86-6)

Safety Data

• Hazardous Substances Data: 118895-86-6(Hazardous Substances Data)

Usage

Chemical structure

A six-carbon alkane chain with six benzyl ether groups attached.

Molecular weight

650.840 g/mol

Physical state

Colorless to pale yellow liquid

Melting point

30-32°C

Solubility

Soluble in most organic solvents, low solubility in water

Applications

a. Protecting group for alcohols and amines in organic synthesis
b. Common reagent in chemical reactions
c. Intermediate in the synthesis of various organic compounds

InChI:InChI=1/C48H50O6/c1-7-19-39(20-8-1)31-49-37-45(51-33-41-23-11-3-12-24-41)47(53-35-43-27-15-5-16-28-43)48(54-36-44-29-17-6-18-30-44)46(52-34-42-25-13-4-14-26-42)38-50-32-40-21-9-2-10-22-40/h1-30,45-48H,31-38H2

Upstream product

• 50-70-4 D-sorbitol 
• 100-39-0 benzyl bromide 
• 69-65-8 mannitol 
• 100-44-7 benzyl chloride 

Downstream Products

• 118895-88-8 3,4-di-O-benzoyl-1,2,5,6-tetra-O-benzyl-D-mannitol 
• 118920-63-1 2-O-benzoyl-1,3,4,5,6-penta-O-benzyl-D-mannitol 
• 118920-62-0 3-O-benzoyl-1,2,4,5,6-penta-O-benzyl-D-mannitol 
• 118920-61-9 1,2,3,5,6-penta-O-benzyl-D-mannitol 
• 118895-87-7 1,2,3,4,6-penta-O-benzyl-D-mannitol 
• 20196-69-4 1,2,5,6-tetra-O-benzyl-D-mannitol 
• 441061-29-6 (2S,3R,4R,5S)-1-butyl-3,4,5-tris(phenylmethoxy)-2-[(phenylmethoxy)methyl]piperidine 
• 227932-82-3 N-butyl 2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol 

Relevant articles and documents

Synthesis of new 4-(tert-Octyl)phenol derivatives and their anticancer activity against human prostate and lung cancer cell lines

4-(tert-Octyl)phenol derivatives bearing the D-mannitol substructure (6a, 6b, 7) were prepared from Dmannitol and evaluated their anticancer activity against human lung (A549) and prostate (Lncap, Du145, PC3) cancer cell lines. Among derivatives tested, the bis(tert-octyl)phenoxy compound 7 exhibited strongest proliferation inhibitory activities against human cancer cell lines tested, especially high sensitivity to human Du145 prostate cancer cells (IC50 = 7.3 μM).

Synthesis of Protected Carbohydrate Derivatives through Homologation of Threose and Erythrose Derivatives with Chiral γ-Alkoxy Allylic Stannanes

Additions of the γ-alkoxy allylic stannanes (S)-1 and (R)-1 and the racemate (RS)-1 to the threose and erythrose aldehyde derivatives 6 and 15 in the presence of BF3*OEt2 or MgBr2*OEt2 were examined in order to establish stereochemical preferences.It was found that (S)-1 and aldehyde 6 afforded the syn,anti,syn adduct 7 in the BF3-promoted reaction, while (R)-1 and 6 gave the syn,syn,syn adduct 8 under MgBr2 conditions.Likewise, (S)-1 and aldehyde 15 yielded the syn,anti,anti adduct 16 with BF3, whereas (R)-1 and 15 led to the syn,syn,anti adduct 17 with MgBr2.The MgBr2-promoted reactions showed sufficient rate differences between the matched and mismatched stannanes to allow the use of racemic stannane (RS)-1 in just over 2-fold excess, whereupon the matched adducts 8 and 17 were favored by greater than 9:1 over the mismatched adducts.The major adducts 7, 8, 16, and 17 were converted to the hexose derivatives 21, 30/31, 34, and 39 by ozonolysis, selective deprotection, and refunctionalization.Adducts 16 and 17 were dihydroxylated with OsO4-NMO to the deoxyoctose precursors 40/41 and 42/43.

Regioselective De-O-benzylation with Lewis Acids

Simple and highly regioselective de-O-benzylations of poly-O-benzylated monosaccharides and polyols with Lewis acids (SnCl4 and TiCl4) were developed.Spectral studies on intermediates complexes showed that three appropriately situated metal chelating functional groups were necessary for the selective de-O-benzylation.