65758-50-1

Basic information

• Product Name: 2,5-ANHYDRO-1,3-O-ISOPROPYLIDENE-6-O-TRITYL-D-GLUCITOL
• Synonyms: 2,5-Anhydro-1,3-O-(1-Methylethylidene)-6-O-(triphenylMethyl)-D-glucitol
• CAS NO: 65758-50-1
• Molecular Formula: C27H28O5
• Molecular Weight: 432.513
• Product Categories: Carbohydrates & Derivatives
• Mol File: 65758-50-1.mol
• Article Data: 1

Chemical Properties

• Melting Point: 185-186°C
• Boiling Point: 576.083°C at 760 mmHg
• Flash Point: 302.204°C
• Appearance: /
• Density: 1.172g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.572
• Storage Temp.: -20°C Freezer
• CAS DataBase Reference: 2,5-ANHYDRO-1,3-O-ISOPROPYLIDENE-6-O-TRITYL-D-GLUCITOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-ANHYDRO-1,3-O-ISOPROPYLIDENE-6-O-TRITYL-D-GLUCITOL(65758-50-1)
• EPA Substance Registry System: 2,5-ANHYDRO-1,3-O-ISOPROPYLIDENE-6-O-TRITYL-D-GLUCITOL(65758-50-1)

Safety Data

• Hazardous Substances Data: 65758-50-1(Hazardous Substances Data)

Usage

Chemical Properties

White to Off-White Solid

InChI:InChI=1/C28H30O5/c1-27(2)30-19-24-26(33-27)25(29)23(32-24)18-31-28(20-12-6-3-7-13-20,21-14-8-4-9-15-21)22-16-10-5-11-17-22/h3-17,23-26,29H,18-19H2,1-2H3/t23-,24+,25+,26?/m1/s1

Upstream product

• 65729-81-9 2,5-anhydro-1,3-O-isopropylidene-D-glucitol 
• 76-83-5 trityl chloride 

Downstream Products

• 68774-48-1 2,5-Anhydro-1-O-trityl-D-mannit 
• 129173-11-1 2,5-anhydro-1,6-bis-O-(triphenylmethyl)-D-glucitol 

Relevant articles and documents

D-arbinose-based synthesis of homo-C-d4T and homo-C-thymidine

2,3,5-Tri-O-benzyl-D-arabinofuranosyl halides (chloride, bromide) were reacted with AllMgBr, MeMgBr, and VinMgBr to furnish anomeric mixtures of the C-glycosyl products. The factors that influenced the β/α ratio are discussed. The α,β-C-vinyl derivative was transformed into 1-deoxy-1-C-hydroxymethyl-β and α-D-arabinofuranoses (2,5-anhydro-D-glucitol and -mannitol, respectively), separable after isopropylidenation step. 2,5-Anhydro-1,3-O-isopropylidene-D-glucitol was converted into 2,5-anhydro-6-O-triphenylmethyl-D-erythro-hex-3,4-enitol and 2,5-anhydro-4,6-di-O-benzoyl-3-deoxy-D-ribo-hexitol, which were coupled with N-3-benzoylthymine under the Mitsunobu conditions to furnish two analogs of nucleosides with a -CH2- insert between sugar moieties and thymine. (Chemical Equation Presented).