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

• 91-09-8 methyl β-L-arabinopyranoside 
• 16713-78-3 methyl 2-O-acetyl-3,4-O-isopropylidene-β-L-arabinopyranoside 
• 87-72-9 L-(+)-arabinose 
• 67-64-1 acetone 
• 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 
• 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 
• 7296-56-2 β-L-arabinopyranose 
• 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 

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 
• 24558-73-4 Methyl-3,4-O-isopropyliden-β-L-ribosid 
• 4421-83-4 methyl 3,4-O-isopropylidene-2-O-p-tolylsulfonyl-β-L-ribopyranoside 
• 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 

Relevant articles and documents

Hafnium trifluoromethanesulfonate catalyzed silyl ether protecting group removing method

The invention provides a hafnium trifluoromethanesulfonate catalyzed silyl ether protecting group removing method. Various silyl ether protecting groups of nearly 50 kinds of substrates can be efficiently removed in 0.5-16 hours at room temperature by taking 0.02mol%-0.3mol% hafnium trifluoromethanesulfonate as a catalyst, a silyl ether protected hydroxyl compound as a substrate and conventional AR methanol as a solvent. 42 kinds of silyl ether protecting group removing products can be obtained at high yield by performing conventional slica column chromatography purification on a crude product. By regulating the use amount of the catalyst, the Hf(OTf)4 catalyst can realize regioselective removal of 1-degree, 2-degree and 3-degree alkyl TBS and aryl TBS protective groups. Moreover, in a proper equivalent scope, the Hf(OTf)4 catalyst can also realize 1) chemoselective removal of different kinds of silica-based protective groups; and 2) chemoselective removal of 1-degree TBS protective groups under the condition of not affecting a majority of common hydroxyl protective groups.

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).