51432-64-5

Basic information

• Product Name: 1,6-di-O-benzoyl-3,4-O-(1-methylethylidene)hexitol
• CAS NO: 51432-64-5
• Molecular Formula: C₂₃H₂₆O₈
• Molecular Weight: 430.4477
• Mol File: 51432-64-5.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 594.2°C at 760 mmHg
• Flash Point: 202°C
• Density: 1.266g/cm³
• Vapor Pressure: 5.77E-15mmHg at 25°C
• Refractive Index: 1.564
• CAS DataBase Reference: 1,6-di-O-benzoyl-3,4-O-(1-methylethylidene)hexitol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-di-O-benzoyl-3,4-O-(1-methylethylidene)hexitol(51432-64-5)
• EPA Substance Registry System: 1,6-di-O-benzoyl-3,4-O-(1-methylethylidene)hexitol(51432-64-5)

Safety Data

• Hazardous Substances Data: 51432-64-5(Hazardous Substances Data)

Usage

General Description

1,6-di-O-benzoyl-3,4-O-(1-methylethylidene)hexitol, also known as pivaloyl-D-mannitol, is a chemical compound commonly used as a reagent in organic chemistry. It is a derivative of D-mannitol, a sugar alcohol, and is typically synthesized by reacting D-mannitol with pivaloyl chloride. The resulting compound is a white crystalline solid that is stable under normal conditions. It is often used as a mild and selective reducing agent in organic synthesis and in the preparation of various functionalized derivatives of carbohydrates. Additionally, pivaloyl-D-mannitol has been investigated for its potential applications in pharmaceuticals and medicinal chemistry due to its unique chemical properties and reactivity.

Upstream product

• 98-88-4 benzoyl chloride 
• 3969-84-4 3,4-di-O-isopropylidene-D-mannitol 
• 67-64-1 acetone 
• 7226-27-9 1,6-di-O-benzoyl-D-mannitol 
• 77-76-9 2,2-dimethoxy-propane 
• 3969-59-3 mannitol triacetonide 
• 69-65-8 mannitol 

Downstream Products

• 3969-84-4 3,4-di-O-isopropylidene-D-mannitol 
• 97579-29-8 C₃₇H₄₆O₆ 
• 97643-27-1 C₃₇H₅₀O₆ 
• 97579-33-4 C₃₄H₄₆O₆ 
• 97579-28-7 C₂₅H₃₀O₆ 
• 97643-26-0 C₂₂H₂₆O₆ 
• 258873-45-9 [[(4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]di(R)-ethylidene]bis-[diphenylphosphine] 
• 159716-52-6 (2S,3R,4R,5S)-3,4-O-(1-methylethylidene)-2,3,4,5-hexanetetraol 
• 404961-42-8 Acetic acid 4-((3aR,4S,8S,8aR)-4,8-dihydroxy-2,2-dimethyl-hexahydro-1,3-dioxa-6-aza-azulen-6-yl)-phenyl ester 
• 404961-35-9 Acetic acid 4-((3aR,4R,8R,8aR)-4,8-dihydroxy-2,2-dimethyl-hexahydro-1,3-dioxa-6-aza-azulen-6-yl)-phenyl ester 
• 404961-39-3 (3aR,4R,8R,8aR)-6-(4-Hydroxy-benzyl)-2,2-dimethyl-hexahydro-1,3-dioxa-6-aza-azulene-4,8-diol 
• 404961-43-9 (3aR,4S,8S,8aR)-6-(4-Hydroxy-phenyl)-2,2-dimethyl-hexahydro-1,3-dioxa-6-aza-azulene-4,8-diol 
• 404961-36-0 (3aR,4R,8R,8aR)-6-(4-Hydroxy-phenyl)-2,2-dimethyl-hexahydro-1,3-dioxa-6-aza-azulene-4,8-diol 
• 51432-65-6 1,6-di-O-benzoyl-3,4-O-isopropylidene-2,5-di-O-p-toluenesulphonyl-D-mannitol 

Relevant articles and documents

Bifunctional acyclic nucleoside phosphonates: synthesis of chiral 9-{3-hydroxy[1,4-bis(phosphonomethoxy)]butan-2-yl} derivatives of purines

We report herein a general method for the synthesis of new types of chiral acyclic nucleoside four-carbon bisphosphonates. The alkylation of 2-amino-6-chloropurine and adenine was performed with (2S,3S)- or (2R,3R)-1,4-[bis(diisopropoxyphosphoryl)methoxy]]-3-[(methylsulfonyl)oxy]butan-2-yl benzoate. Alkylations provided (2R,3R) or (2S,3S) N9-substituted nucleobases, which were further converted to other derivatives. These conversions included either a modification of the nucleobase or transformation of the bisphosphonate chain. Subsequent deprotection of the diisopropyl esters with bromotrimethylsilane provided the resulting (2R,3R)- or (2S,3S)-bisphosphonic acids.

Highly Flexible Synthetic Routes to Functionalized Phospholanes from Carbohydrates

Highly functionalized phospholanes 15, 17, and 26 and the corresponding diastereomers in which the configurations of the phospholane carbon-2 and carbon-5 are inverted can be readily prepared from D-mannitol by displacement of the appropriate dimesylate or cyclic sulfate with dilithium-phosphide reagents. The diols from which these ligands are prepared can also be converted into diarylphosphinite ligands. A route to related monophosphines bearing hemilabile tert-butylthio groups is also described. Complexes of these ligands and of related deprotected derivatives are potentially useful for enantioselective catalysis in organic and aqueous media.

SYNTHESIS AND CONFORMATIONS OF 2,3:4,5- AND 2,4:3,5-DI-O-ISOPROPYLIDENE-D-MANNITOL

The 2,3:4,5- (8) and 2,4:3,5-di-O-isopropylidene (10) derivatives of D-mannitol have been prepared from 1,6-di-O-benzoyl-D-mannitol and their structures established by (13)C-n.m.r. spectroscopy.The 1,3-dioxane rings in 10 adopt a skew conformation and the sugar carbon chain in 8 is bent around the C-3-C-4 bond, as found by i.r. data and molecular mechanics calculations.Oxidation of 8 with pyridinium dichromate gave 2,3:4,5-di-O-isopropylidene-D-mannono-1,6-lactone (12).