261713-59-1

Basic information

• Product Name: 1,5-Anhydro-1,1-C-[(2,2-dimethyl-1,3-propanediyl)bis(oxy)]-2,3,4,6-tetrakis-O-(phenylmethyl)-D-glucitol
• Synonyms: 1,5-Anhydro-1,1-C-[(2,2-dimethyl-1,3-propanediyl)bis(oxy)]-2,3,4,6-tetrakis-O-(phenylmethyl)-D-glucitol;(8R,9R,10S,11R)-9,10,11-Tris(benzyloxy)-8[(benzyloxy)methyl]-3,3-dimethyl-1,5-trioxaspiro[5.5]undecane
• CAS NO: 261713-59-1
• Molecular Formula: C₃₉H₄₄O₇
• Molecular Weight: 624.76
• Mol File: 261713-59-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,5-Anhydro-1,1-C-[(2,2-dimethyl-1,3-propanediyl)bis(oxy)]-2,3,4,6-tetrakis-O-(phenylmethyl)-D-glucitol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-Anhydro-1,1-C-[(2,2-dimethyl-1,3-propanediyl)bis(oxy)]-2,3,4,6-tetrakis-O-(phenylmethyl)-D-glucitol(261713-59-1)
• EPA Substance Registry System: 1,5-Anhydro-1,1-C-[(2,2-dimethyl-1,3-propanediyl)bis(oxy)]-2,3,4,6-tetrakis-O-(phenylmethyl)-D-glucitol(261713-59-1)

Safety Data

• Hazardous Substances Data: 261713-59-1(Hazardous Substances Data)

Usage

Chemical structure

1,5-Anhydro-1,1-C-[(2,2-dimethyl-1,3-propanediyl)bis(oxy)]-2,3,4,6-tetrakis-O-(phenylmethyl)-D-glucitol

Type of compound

Chemical compound

Usage

Surfactant and antistatic agent

Industries

Personal care and household products

Derivative of

D-glucitol

Contains

Multiple phenylmethyl groups

Surfactant properties

Contributed by phenylmethyl groups

Function

Reduces surface tension and improves dispersion of other ingredients in formulations

Popularity

Used in cosmetics and detergent industries

Antistatic properties

Useful in hair care products and fabric softeners

Upstream product

• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 

Downstream Products

• 306968-34-3 3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-2-heptulose 2,2-dimethylpropane-1,3-diyl acetal 
• 261713-60-4 3,4,5,7-tetra-O-benzyl-1-deoxy-2-O-(3-hydroxy-2,2-dimethylpropyl)-D-gluco-hept-1-enitol 
• 261713-64-8 1,3,4,5-tetra-O-benzyl-7-deoxy-6-O-(2,2-dimethyl-3-oxopropyl)-L-xylo-hept-6-en-2-ulose 
• 261713-62-6 1,3,4,5-tetra-O-benzyl-7-deoxy-6-O-(3-tert-butyldimethylsilyloxy-2,2-dimethylpropyl)-L-xylo-hept-6-en-2-ulose 
• 261713-61-5 3,4,5,7-tetra-O-benzyl-1-deoxy-2-O-(3-tert-butyldimethylsilyloxy-2,2-dimethylpropyl)-D-gluco-hept-1-enitol 

Relevant articles and documents

A highly efficient and shortcut synthesis of cyclitol derivatives via spiro sugar ortho esters

Preparation of cyclitol derivatives from sugar lactones via spiro sugar ortho esters is described. The key steps are the novel enol ether formation from sugar ortho esters with A1Me3 and the efficient intramolecular aldol cyclization of alkyl enol ethers with ZnCl2 in THF/H2O. Firstly, the spiro sugar ortho esters 3a-c were prepared from the benzyl protected sugar lactones 1a-c and 2,2-dimethylpropanediol (2). These ortho esters were efficiently converted into the enol ethers 5a-c by the treatment of AlMe3 in CH2Cl2. The initial step of this reaction was the pyran ring cleavage accompanied by the methyl anion insertion, and the second was the dioxane ring opening caused by the Lewis acidity of AlMe3. The resulting alkyl enol ethers were treated with DMSO/Ac2O, and the formed keto compounds were converted into the carbasugars 9a-c by the ZnCl2-catalyzed aldol cyclization in THF/H2O. The overall yields of 9a, 9b, and 9c based on the corresponding lactones 1a-c were 64, 64, and 54%, respectively. (C) 2000 Elsevier Science Ltd.

Facile ring transformation from gluconolactone to cyclitol derivative via spiro sugar ortho ester

(Formula presented) A short step preparation of cyclitol derivative 8 which is a versatile synthon for the synthesis of valiolamine and its related compounds is described. Key steps in this preparation are a novel enol ether formation from spiro sugar ortho esters with AIMe3 and an intramolecular Aldol condensation of alkyl enol ethers catalyzed by ZnCl2 in THF-H2O. With these reactions, gluconolactone derivative 1 was efficiently converted into 8 in short steps.