145852-76-2

Basic information

• Product Name: 3,6-Di-O-benzyl-D-glucal
• Synonyms: 1,5-anhydro-3,6-di-O-benzyl-2-deoxy-D-arabino-hex-1-enitol
• CAS NO: 145852-76-2
• Molecular Formula: C₂₀H₂₂O₄
• Molecular Weight: 326.3863
• Mol File: 145852-76-2.mol
• Article Data: 12

Chemical Properties

• Melting Point: 129℃
• Boiling Point: 480.5°C at 760 mmHg
• Flash Point: 244.4°C
• Density: 1.19g/cm³
• Vapor Pressure: 4.84E-10mmHg at 25°C
• Refractive Index: 1.596
• CAS DataBase Reference: 3,6-Di-O-benzyl-D-glucal(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-Di-O-benzyl-D-glucal(145852-76-2)
• EPA Substance Registry System: 3,6-Di-O-benzyl-D-glucal(145852-76-2)

Safety Data

• Safety Statements: S24/25:Avoid contact with skin and eyes.
• Hazardous Substances Data: 145852-76-2(Hazardous Substances Data)

Upstream product

• 13265-84-4 D-glucal 
• 100-39-0 benzyl bromide 
• 791790-13-1 3-O-benzyl-4,6-O-p-methoxybenzylidene-D-glucal 
• 356067-96-4 1,5-anhydro-3-O-benzyl-2-deoxy-4-O-(4-methoxybenzyl)-D-arabinohex-1-enitol 
• 913258-73-8 (2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3-(4-methoxy-benzyloxy)-3,4-dihydro-2H-pyran 
• 312623-79-3 (4aR,8R,8aS)-2-(4-methoxyphenyl)-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxin-8-ol 
• 2873-29-2 D-glucal triacetate 

Downstream Products

• 196704-47-9 Acetic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-((2R,3S,4R)-4-benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester 
• 196704-60-6 3,4-di-O-benzyl-2-O-pivaloyl-6-O-triisopropylsilyl-β-D-galactopyranoside-(1->4)-3,6-di-O-benzyl-D-glucal 
• 196705-04-1 3,4-di-O-benzyl-2-O-pivaloyl-6-O-triisopropylsilyl-β-D-galactopyranoside-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside-(1->4)-3,6-di-O-benzyl-D-glucal 
• 129840-37-5 1,5-anhydro-3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-D-arabino-hex-1-enitol 
• 80040-79-5 3,4,6-tri-O-benzyl-D-galactal 
• 385421-75-0 3,6-di-O-benzyl-4-O-levulinoyl-glucal 
• 1279711-36-2 3,6-di-O-benzyl-4-deoxy-D-glucal 
• 1279711-53-3 methyl 3,6-di-O-benzyl-4-deoxy-1R-D-galactopyranose 
• 1279711-67-9 C₂₀H₂₂O₄ 

Relevant articles and documents

Microwave-assisted regioselective benzylation: An access to glycal derivatives with a free hydroxyl group at C4

D-glucal, D-galactal, and their 6-O-TBDMS derivatives were benzylated in a two-step procedure under microwave conditions. In the first step glycals were converted into dibutylstannylene acetal or tributyltin ether intermediates, which were next alkylated with benzyl bromide in the presence of Bu 4NBr. In all cases the 4-OH group stayed unsubstituted. Microwave-assisted benzylation contributes to a significant reduction of the reaction time in comparison with the classical synthesis, which requires several hours of heating. Supplemental materials are available for this article. Go to the publisher's online edition of Journal of Carbohydrate Chemistry to view the free supplemental file.

Glycal glycosylation and 2-nitroglycal concatenation, a powerful combination for mucin core structure synthesis

(Chemical Equation Presented) A 3,4-O-unprotected galactal derivative having bulky 6-O-TIPS protection (compound 2) could be regioselectively 3-O-glycosylated with O-(galactopyranosyl) trichloroacetimidates; depending on the protecting group pattern stere

Design, synthesis and biological activity of carbohydrate-containing peptidomimetics as new ligands for the human tachykinin NK-2 receptor

Enantiopure cycloadducts between glycals and alkyl or aryl heterodienes were selected as small, rigid, nonpeptide molecules able to superimpose to the structure of the cyclopeptide tachykinin NK-2 antagonist 1. The presence of three aromatic groups in the pyranose ring resulted essential for NK-2 affinity, while an increase in activity was shown by the corresponding sulfoxides.