6960-39-0

Basic information

• Product Name: Methyl 3,4-Isopropylidene-β-L-arabinopyranoside
• Synonyms: Methyl 3,4-Isopropylidene-β-L-arabinopyranoside;Methyl 3,4-O-(1-Methylethylidene)-β-L-arabinopyranoside;NSC 69871
• CAS NO: 6960-39-0
• Molecular Formula: C₉H₁₆O₅
• Molecular Weight: 204.22034
• Product Categories: Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 6960-39-0.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 314.9°C at 760 mmHg
• Flash Point: 144.3°C
• Appearance: /
• Density: 1.23g/cm³
• Vapor Pressure: 3.87E-05mmHg at 25°C
• Refractive Index: 1.491
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate
• CAS DataBase Reference: Methyl 3,4-Isopropylidene-β-L-arabinopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 3,4-Isopropylidene-β-L-arabinopyranoside(6960-39-0)
• EPA Substance Registry System: Methyl 3,4-Isopropylidene-β-L-arabinopyranoside(6960-39-0)

Safety Data

• Hazardous Substances Data: 6960-39-0(Hazardous Substances Data)

Usage

Chemical Properties

Orange Oil

InChI:InChI=1/C9H16O5/c1-9(2)13-5-4-12-8(11-3)6(10)7(5)14-9/h5-8,10H,4H2,1-3H3

Upstream product

• 1053735-09-3 tert-Butyl-((3aS,6S,7R,7aS)-6-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy)-dimethyl-silane 
• 87-72-9 L-(+)-arabinose 
• 67-64-1 acetone 
• 16713-78-3 methyl 2-O-acetyl-3,4-O-isopropylidene-β-L-arabinopyranoside 
• 91-09-8 methyl β-L-arabinopyranoside 
• 7296-56-2 β-L-arabinopyranose 
• 5328-37-0 L-arabinose 
• 64429-69-2 methyl 3,4-O-isopropylidene-2-O-[(methylthio)thiocarbonyl]-β-L-arabinopyranoside 
• 6847-76-3 methyl 3,4-O-isopropylidene-β-L-Ara 2-O-tosylate 
• 77-76-9 2,2-dimethoxy-propane 
• 91-09-8 methyl β-L-arabinopyranoside 
• 51830-02-5 bromo-2,3,4-O-triacetyl-α/β-L-arabinopyranoside 
• 38088-60-7 methyl 3,4-O-isopropylidene-β-L-arabinopyranoside 
• 105260-77-3 methyl 2-O-acetyl-3,4-O-isopropylidene-α-L-arabinopyranoside 

Downstream Products

• 105260-80-8 methyl 2-O-acetyl-3-O-trityl-β-L-arabinopyranoside 
• 105260-79-5 methyl 2-O-acetyl-4-O-trityl-β-L-arabinopyranoside 
• 105260-84-2 methyl 2,3-di-O-acetyl-4-O-trityl-β-L-arabinopyranoside 
• 105260-85-3 methyl 2,4-di-O-acetyl-3-O-trityl-β-L-arabinopyranoside 
• 22900-10-3 (4R,5S)-tetrahydro-2H-pyran-2,4,5-triol 
• 1373340-79-4 methyl 3,4-O-isopropylidene-2-O-phenoxythiocarbonyl-β-L-arabinopyranoside 
• 64429-69-2 methyl 3,4-O-isopropylidene-2-O-[(methylthio)thiocarbonyl]-β-L-arabinopyranoside 
• 112346-33-5 methyl 2-O-p-tolylsulfonyl-β-L-arabinopyranoside 
• 19773-91-2 methyl-(β-L-erythro-3-deoxy-pentopyranoside) 
• 16713-84-1 Methyl-3,4-di-O-acetyl-2-O-(p-tolylsulfonyl)-β-L-arabinopyranosid 
• 64503-69-1 methyl-[O³,O⁴-((S)-benzylidene)-O²-(toluene-4-sulfonyl)-β-L-arabinopyranoside] 
• 6059-86-5 methyl 2-O-benzoyl-β-L-arabinopyranoside 
• 4421-83-4 methyl 3,4-O-isopropylidene-2-O-p-tolylsulfonyl-β-L-ribopyranoside 
• 24558-73-4 Methyl-3,4-O-isopropyliden-β-L-ribosid 

Relevant articles and documents

Hafnium Triflate as a Highly Potent Catalyst for Regio- and Chemoselective Deprotection of Silyl Ethers

As a Group IVB transition metal Lewis acid, hafnium triflate [Hf(OTf) 4 ] exhibited exceptionally high potency in desilylations. Since the amounts of Hf(OTf) 4 required for the deprotection of 1°, 2°, 3° alkyl and aryl tert -butyldimethylsilyl (TBS) ethers are significantly different, ranging from 0.05 mol% to 3 mol%, regioselective deprotection of TBS could be easily implemented. Moreover, chemoselective cleavage of different silyl ethers or removal of TBS in the presence of most hydroxyl protecting groups was also accomplished. NMR analyses of silyl products from TBS deprotection indicated that Hf(OTf) 4 -catalyzed desilylation may proceed via different mechanisms, depending on the solvent used.

A Green and Sustainable Route to Carbohydrate Vinyl Ethers for Accessing Bioinspired Materials with a Unique Microspherical Morphology

Synthesizing chemicals and materials from renewable sources is one of the main aims of modern science. Carbohydrates represent excellent renewable natural raw materials that are ecofriendly, inexpensive, and biologically compatible. A green procedure has been developed for the vinylation of carbohydrates by using readily available calcium carbide. Various carbohydrates were utilized as starting materials, resulting in mono-, di-, and tetravinyl ethers in high to excellent yields (81–92 %). The synthesized biobased vinyl ethers were utilized as monomers in free radical and cationic polymerizations. A unique combination of a smooth surface and intrinsic microcompartments was achieved in the synthesized materials. Two types of biobased materials were prepared involving microspheres and intrinsic hollow compartments in polymers. Scanning electron microscopy with built-in ion beam cutting was applied to reveal the spatial hierarchical structures in 3D space.

Catalytic asymmetric epoxidation of alkenes with arabinose-derived uloses

Four L-erythro-2-uloses were readily prepared from L-arabinose via a reaction sequence involving Fischer glycosidation, acetalization and oxidation. Bulky steric sensors at the anomeric center could enhance the stereoselectivity of the dioxirane epoxidation and one of the uloses performed with good enantioselectivity towards trans-stilbene (up to 90% ee). However, the catalysts decomposed during the epoxidation and the maximum chemical yield was only 13% under the basic conditions. Three L-threo-3-uloses could overcome the decomposition problem based on the electron withdrawing effect of the ester group(s) α to the ketone functionality. The best chemical yield was up to 93% using a ketone with two flanking ester groups. One of the improved uloses displayed moderate enantioselectivity towards trans-disubstituted and trisubstituted alkenes (40-68% ee).