129115-89-5

Basic information

• Product Name: 2,5-Anhydro-3,4-dibenzyl-D-glucitol
• Synonyms: 2,5-Anhydro-3,4-dibenzyl-D-glucitol;2,5-Anhydro-3,4-bis-O-(phenylMethyl)-D-glucitol
• CAS NO: 129115-89-5
• Molecular Formula: C₂₀H₂₄O₅
• Molecular Weight: 344.40156
• Product Categories: Carbohydrates & Derivatives;Intermediates
• Mol File: 129115-89-5.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Solubility: Dichloromethane, Ether
• CAS DataBase Reference: 2,5-Anhydro-3,4-dibenzyl-D-glucitol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Anhydro-3,4-dibenzyl-D-glucitol(129115-89-5)
• EPA Substance Registry System: 2,5-Anhydro-3,4-dibenzyl-D-glucitol(129115-89-5)

Safety Data

• Hazardous Substances Data: 129115-89-5(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Oil

Uses

Protected D-Glucitol.

Upstream product

• 70337-25-6 4,5-O-isopropylidene-D-arabinose diethyldithioacetal 
• 222408-63-1 3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-5,6-O-isopropylidene-D-glucitol 
• 222408-64-2 3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-D-glucitol 
• 175606-34-5 2,3-di-O-benzyl-4,5-O-isopropylidene-D-arabinose diethyl dithioacetal 
• 106929-09-3 (2S,3R,4R)-2,3-dibenzyloxy-4,5-isopropylidenedioxypentanal 
• 100-39-0 benzyl bromide 
• 1941-50-0 D-arabinose diethyl dithioacetal 
• 111555-72-7 R,R-3,4-dibenzyloxy-threo-hexa-1,5-diene 
• 222408-65-3 2,5-anhydro-3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-D-glucitol 
• 157363-84-3 1,2:5,6-dianhydro-3,4-di-O-benzyl-L-iditol 
• 172147-86-3 Methanesulfonic acid (1R,2S,3S,4R)-2,3-bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-4-methanesulfonyloxy-pentyl ester 

Downstream Products

• 102208-54-8 2,5-anhydro-3,4,6-tri-O-benzyl-D-glucitol 
• 300807-58-3 ((2R,3R,4R,5S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-methanol 

Relevant articles and documents

Simple and efficient synthesis of 2,5-anhydro-d-glucitol

The synthesis of 2,5-anhydro-d-glucitol is described via intramolecular cyclization of diepoxide using ammonium formate in MeOH by a microwave-assisted reaction. The overall yield was 32% from d-mannitol derivative involving seven steps.

Preparation of 2,5-anhydrohexitols (part I). Silicon-directed stereocontrolled cyclization

Stereoselective chain-extension of carbohydrate aldehydes with the hydroxymethylating reagent (dimethylphenylsilyl)methylmagnesium chloride (1) followed by acid-mediated cyclization gives access to 2,5-anhydro-hexitols. The stereoselectivity of the ring closure depends on the nature of the acid, i.e., treatment with excess BF3·Et2O or catalytic H2SO4 leads to tetrahydrofurans with 2,3-cis or 2,3-trans configuration, respectively. Concomitant elimination is effectively suppressed in case of cyclisation of the more sterically hindered isopropyl substituted silanes.