24807-96-3

Usage

Uses

Used in Organic Chemistry:
1,2-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE 3-ACETATE is used as a protecting group for the hydroxyl groups of glucose, facilitating the synthesis of various organic compounds by preventing unwanted reactions at the hydroxyl groups.
Used in Bioorganic Synthesis:
In the bioorganic synthesis industry, 1,2-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE 3-ACETATE is utilized as a starting material for the synthesis of carbohydrate derivatives, which are essential in the development of complex biological molecules and pharmaceuticals.
Used in Pharmaceutical Compounds Synthesis:
1,2-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE 3-ACETATE is employed as a key intermediate in the synthesis of pharmaceutical compounds, contributing to the development of new drugs and therapeutic agents. Its unique structure allows for the creation of novel carbohydrate-based molecules with potential medicinal properties.

InChI:InChI=1/C11H18O7/c1-5(13)15-8-7(6(14)4-12)16-10-9(8)17-11(2,3)18-10/h6-10,12,14H,4H2,1-3H3/t6-,7-,8+,9-,10-/m1/s1

Upstream product

• 67-56-1 methanol 
• 17225-57-9 3-O-acetyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hexo-5-enofuranose 
• 582-52-5 1,2:5,6-diacetone-D-glucose 
• 98032-70-3 Acetic acid (3aR,5R,6S,6aR)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 16713-80-7 3-O-acetyl-1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 109680-97-9 O³-acetyl-O¹,O²-isopropylidene-O⁶-trityl-α-D-glucofuranose 
• 2592-46-3 O³-acetyl-O⁵,O⁶-dibenzoyl-O¹,O²-isopropylidene-α-D-glucofuranose 
• 104652-55-3 3-O-acetyl-1,2-O-isopropylidene-6-O-(p-nitrobenzoyl)-D-glucofuranose 
• 19189-68-5 3-O-acetyl-1,2-O-isopropylidene-6-O-tosyl-D-glucofuranose 
• 7057-09-2 1,2-O-isopropylidene-5-deoxy-α-D-glucofuranose 
• 220325-42-8 (1S,4R)-1-<(E)-2-<(3aR,5R,6R,6aR)-6-(benzyloxy)-5-<2-(tert-butyldimethylsilyloxy)ethyl>-tetrahydro-2,2-dimethylfuro<2,3-d>-1,3-dioxol-6-yl>vinyl>-7,7-dimethylbicyclo<2.2.1>-heptan-2-one 
• 10470-80-1 1,2,3,4,6-penta-O-acetyl-5-thio-α,β-D-glucopyranose 
• 16505-91-2 (3R,4S,5S,6R)-6-(hydroxymethyl)tetrahydro-2H-thiopyran-2,3,4,5-tetraol 
• 2592-44-1 3-O-acetyl-1,2-O-isopropylidene-5,6-O-di-toluene-p-sulphonyl-α-D-glucofuranose 

Relevant academic research and scientific papers

A mild and efficient method for the chemoselective deprotection of acetonides with lanthanum(III) nitrate hexahydrate

Acetonides are hydrolyzed selectively and efficiently with lanthanum(III) nitrate hexahydrate in acetonitrile. The method has good compatibility with other sensitive hydroxyl protecting groups such as trityl, TBDMS, THP, OAc, OBz and OBn.

The role of the C-3 substituent in the asymmetric dihydroxylation of hexo-5-enofuranosides

Asymmetric dihydroxylation of vinyl furanosides 1-6 by use of OsO4, AD-mix-α and β is described yielding the corresponding hexofuranose sugars. Vinyl furanosides 2 and 3, with an ester group at C-3, and vinyl manno furanoside 5 on asymmetric dihydroxylation with AD-mix α exhibited high R diastereoselectivity at C-5. Reversal in diastereoselectivity at C-5 was observed for the 3-deoxy vinyl furanoside 6 giving furanosaccharide 6S with the S configuration at C-5.

Lithium tetrafluoroborate: A mild and efficient reagent for the cleavage of dimethoxytrityl ethers

A mild and efficient method for the cleavage of dimethoxytrityl ethers using lithium tetrafluoroborate is reported.

Transacetalation: a convenient, nonaqueous method for effecting the deprotection of isopropylidene and benzylidene derivatives of sugars

Sugar isopropylidene and benzylidene derivatives can be readily deprotected under nonaqueous conditions by treatment of a dichloromethane solution of the protected sugar with an excess of a sacrificial glycol in the presence of a catalytic amount of p-toluenesulfonic acid.The reaction is conveniently monitored by GLC, and the fully or partially deprotected product precipitates from solution.

Anthracyclinones, Part 4. The Use of DBN or DBU in a Novel Extension of the Marschalk Reaction leading to Hydroxyglycitylanthraquinones

Leuco-quinizarin (1) with propanal, 3-O-(p-chlorobenzyl)-(or 3-O-acetyl)-1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose (6a) or (6c), or 3-O-acetyl-3-C-ethynyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose (6b) in dimethylformamide soluti