817620-70-5

Basic information

• Product Name: L-Arabinopyranoside,methyl3,4-O-(1-methylethylidene)-(9CI)
• Synonyms: L-Arabinopyranoside,methyl3,4-O-(1-methylethylidene)-(9CI)
• CAS NO: 817620-70-5
• Molecular Formula: C9H16O5
• Molecular Weight: 204.22034
• Product Categories: METHYL
• Mol File: 817620-70-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: L-Arabinopyranoside,methyl3,4-O-(1-methylethylidene)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: L-Arabinopyranoside,methyl3,4-O-(1-methylethylidene)-(9CI)(817620-70-5)
• EPA Substance Registry System: L-Arabinopyranoside,methyl3,4-O-(1-methylethylidene)-(9CI)(817620-70-5)

Safety Data

• Hazardous Substances Data: 817620-70-5(Hazardous Substances Data)

Upstream product

• 67-64-1 acetone 
• 91-09-8 methyl β-L-arabinopyranoside 
• 77-76-9 2,2-dimethoxy-propane 
• 6847-76-3 methyl 3,4-O-isopropylidene-β-L-Ara 2-O-tosylate 
• 64429-69-2 methyl 3,4-O-isopropylidene-2-O-[(methylthio)thiocarbonyl]-β-L-arabinopyranoside 
• 87-72-9 L-(+)-arabinose 
• 5328-37-0 L-arabinose 
• 7296-56-2 β-L-arabinopyranose 
• 105260-77-3 methyl 2-O-acetyl-3,4-O-isopropylidene-α-L-arabinopyranoside 
• 38088-60-7 methyl 3,4-O-isopropylidene-β-L-arabinopyranoside 
• 51830-02-5 bromo-2,3,4-O-triacetyl-α/β-L-arabinopyranoside 
• 91-09-8 methyl β-L-arabinopyranoside 
• 16713-78-3 methyl 2-O-acetyl-3,4-O-isopropylidene-β-L-arabinopyranoside 
• 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

• 87-72-9 L-ribose 
• 24558-73-4 Methyl-3,4-O-isopropyliden-β-L-ribosid 
• 6059-86-5 methyl 2-O-benzoyl-β-L-arabinopyranoside 
• 64503-69-1 methyl-[O³,O⁴-((S)-benzylidene)-O²-(toluene-4-sulfonyl)-β-L-arabinopyranoside] 
• 112346-33-5 methyl 2-O-p-tolylsulfonyl-β-L-arabinopyranoside 
• 64429-69-2 methyl 3,4-O-isopropylidene-2-O-[(methylthio)thiocarbonyl]-β-L-arabinopyranoside 
• 863998-30-5 methyl 3,4-O-isopropylidene-2-O-methanesulfonyl-β-D-arabinopyranoside 
• 40147-20-4 methyl-[O²-(toluene-4-sulfonyl)-β-D-arabinopyranoside] 
• 38088-60-7 methyl 3,4-O-isopropylidene-β-D-ribopyranoside 
• 95158-28-4 O⁴-methyl-D-threo-[2]pentosulose-bis-phenylhydrazone 
• 863998-29-2 methyl 3,4-O-isopropylidene-2-O-methanesulfonyl-α-D-arabinopyranoside 
• 4421-83-4 methyl 3,4-O-isopropylidene-2-O-p-tolylsulfonyl-β-L-ribopyranoside 
• 53796-89-7 methyl 3,4-O-isopropylidene-2-O-p-tolylsulfonyl-β-D-ribopyranoside 

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.

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.

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The invention relates to a method for preparing 2-deoxidation-L-ribose based on L-arabinose as a raw material. The method comprises following seven steps: protection, group activation, transformation, deprotection and purification. Synthesis reaction cond

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An improved and practical route for a large-scale synthesis of 2-deoxy-L-ribose starting from L-arabinose has been developed. This is the first reported synthesis of 2-deoxy-L-ribose in which deoxygenation has been mediated by hypophosphite reagents instead of by organotin reagents.

Iodine/toluenesulfonic acid: A novel catalyst for isopropylidenation in carbohydrate chemistry

A novel catalyst for O-isopropylidenation of carbohydrates, a mixture of toluenesulfonic acid and iodine, was developed.

Improved syntheses of d-ribo- and 2-deoxy-d-ribofuranose phospho sugars from methyl β-d-ribopyranoside

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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).