14440-56-3

Usage

Uses

Used in Organic Synthesis:
2,3:5,6-Di-O-isopropylidene-D-mannono-1,4-lactone is used as a key intermediate in organic synthesis for the preparation of complex natural products and pharmaceuticals. Its role as a versatile intermediate is crucial in the development of new compounds with potential therapeutic and industrial applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,3:5,6-Di-O-isopropylidene-D-mannono-1,4-lactone is used as a building block for the synthesis of novel drug candidates. Its ability to protect hydroxyl groups in carbohydrates makes it a valuable component in the design and synthesis of complex carbohydrate-based drugs.
Used in Modification of Natural Products:
2,3:5,6-Di-O-isopropylidene-D-mannono-1,4-lactone is used as a modifying agent in the alteration of sugars and other natural products to change their properties. This modification can enhance the stability, solubility, or biological activity of these natural products, leading to improved performance in various applications.
Used in Research and Development:
In the field of research and development, 2,3:5,6-Di-O-isopropylidene-D-mannono-1,4-lactone is used as a valuable tool for studying the properties and reactivity of carbohydrates and their derivatives. Its unique structure allows researchers to explore new synthetic pathways and develop innovative methods for the preparation of complex carbohydrate-based compounds.

Upstream product

• 7757-38-2 2,3,5,6-di-O-isopropylidene-D-mannofuranose 
• 78964-16-6 2,3;5,6-di-O-isopropylidene-β-D-mannofuranose 
• 95517-29-6 1-C-nitroso-2,3:5,6-di-O-isopropylidenemannofurasonyl chloride 
• 1165952-91-9 cyclohexa-1,3-diene 
• 14131-84-1 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 
• 160701-79-1 2,3:5,6-Di-O-isopropylidene-1-(2-thiazolyl)-α-D-mannofuranose 
• 77-76-9 2,2-dimethoxy-propane 
• 26301-79-1 D-mannono-1,4-lactone 
• 89-65-6 isoascorbic acid 
• 131444-81-0 5-O-acetyl-1,2-dideoxy-3,4:6,7-di-O-isopropylidene-D-manno-hept-1-enitol 
• 3458-28-4 D-Mannose 
• 7757-38-2 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 
• 159423-92-4 (R)-3-{(4R,5R)-5-[(R)-Acetoxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-diazo-3-hydroxy-propionic acid ethyl ester 
• 159423-91-3 4-O-acetyl-2,3:5,6-di-O-isopropylidene-aldehydo-D-mannose 

Downstream Products

• 119842-22-7 2,3:5,6-di-O-isopropylidene-1-C-phenyl-D-mannofuranoside 
• 14131-84-1 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 
• 329010-28-8 (4R,5R)-4-(tert-butyldiphenylsilanoxy)-5-[octa-2(Z),5(E)-dienyl]-tetrahydrofuran-2-one 
• 550316-70-6 (4R,5R)-4-(tert-butyldiphenylsilanyloxy)-5-vinyl-tetrahydrofuran-2-one 
• 114488-17-4 (-) Altholactone 
• 120019-23-0 (-)-7-epi-altholactone 
• 162808-24-4 C-phenyl 2,3-O-isopropylidene-β-D-mannofuranoside 
• 162808-23-3 (3aS,4R,6S,6aR)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-phenyltetrahydrofuro[3,4-d][1,3]dioxole 
• 162630-69-5 Z-(C-phenyl 5,6-dideoxy-2-O-trifluoromethanesulphonyl-α-D-lyxo-heptofuranosi)uro-5-enono-3,7-lactone 
• 14440-51-8 1,6-anhydro-2,3-O-isopropylidene-β-D-mannopyranose 
• 150160-98-8 2,3-O-Isopropylidene-6-O-(p-tolylsulfonyl)-D-mannono-1,4-lactone 

Relevant academic research and scientific papers

C-Triazolyl β-d-furanosides as LpxC inhibitors: Stereoselective synthesis and biological evaluation

C-Triazolyl β-d-furanosides 10a-f were synthesized in a stereocontrolled way, starting from d-mannose. In the key steps of the synthesis a diastereoselective reduction of hemiketal 14 and a Cu(I) catalyzed [3+2]-cycloaddition of central building block 18

A New Synthesis for 2-Deoxy-KDO, a Potent Inhibitor of CMP-KDO Synthetase.

A new synthesis for the 2-deoxy KDO 2 by aldolic condensation of 2,3:5,6-di-O-isopropylidene-4-acetyl-D-manno aldehyde 4 with ethyl diazoacetate and conversion of the condensation product to the 3-deoxy-2-diazo ester 13 in four steps is reported.Rhodium (II) decomposition of the diazo compound leads to the α-anomer of the 2-deoxy pyranose 14 stereospecifically.Removal of isopropylidene groups and ester hydrolysis provides 2, a potent inhibitor of CMP-KDO synthetase.

Synthesis and use of 6,6,6-trifluoro-L-fucose to block core-fucosylation in hybridoma cell lines

Many monoclonal antibodies (mAbs) used in cancer immunotherapy mediate tumour cell lysis by recruiting natural killer (NK) cells; a phenomenon known as antibody-dependent cellular cytotoxicity (ADCC). Eliminating core-fucose from the N-glycans of a mAb enhances its capacity to induce ADCC. As such, inhibitors of fucosylation are highly desirable for the production of mAbs for research and therapeutic use. Herein, we describe a simple synthesis of 6,6,6-trifluoro-L-fucose (F3Fuc), a metabolic inhibitor of fucosylation, and demonstrate the utility of this molecule in the production of low-fucose mAbs from murine hybridoma cell lines.

Chiral Models of the Furenone Moiety of Germacranolide Sesquiterpenes

A procedure is outlined for converting 2,3:5,6-di-O-isopropylidene-D-mannose (4, diacetone mannose), by a series of simple, efficient steps, into the unsaturated hydroxy esters 14 and 15, which are then oxidized by Fetizon's reagent to afford the dienones 3a and 3b, these being analogues of the furenone system found in many germacranolide sesquiterpenes.

An efficient synthesis of L-allono-1,4-lactone from 2,3:5,6-di-O- isopropylidene-D-mannono-1,4-lactone

We reported herein an efficient synthesis of L-allono-1,4-lactone from 2,3:5,6-di-O-isopropylidene-D-mannono-1,4-lactone in five steps. The key feature of this method involved a one-pot, 'double inversion' procedure at the stereocenters of C-4 and C-5 of D-mannono-1,4-lactone to afford the target molecule.

Syntheses of (3R,4R,5R,6R)-tetrahydroxyazepane (1,6-dideoxy-1,6-imino-D-mannitol) and (3S,4R,5R,6R)-tetrahydroxyazepane (1,6-dideoxy-1,6-imino-D-glucitol)

Syntheses of 1,6-dideoxy-1,6-imino-D-mannitol (D-mannoazepane) (1) and 1,6-dideoxy-1,6-imino-D-glucitol (D-glucoazepane) (3) from D-isoascorbic acid and D-glucono-1,5-lactone, respectively, are described. The key step in both routes involved reductive aminative 1,6-cyclization with retention of configurations to give the corresponding lactams, which were subsequently reduced to afford compounds 1 and 3 in 24 and 28.5%, overall yield, respectively.

Efficient synthesis of α,β-unsaturated γ-lactones linked to sugars

A series of structurally diverse unsaturated sugar-derived lactones has been prepared. α,β-Butenolides were introduced to the sugar moiety starting from epoxides, while α-methylene-γ-lactones were constructed from a carbonyl precursor, either an aldehyde, a ketone or a lactone. In the last case, an unprecedented Reformatsky-type reaction has been developed.

Dimerization of aldosuloses and aldonolactones into branched higher carbon sugars

Homo-dimerizations of a variety of aldosulose and aldonolactone derivatives via aldol and Claisen reactions have been achieved, leading to novel branched higher carbon sugars in a highly stereoselective manner.

CARBOHYDRATE PHOSPHONATE DERIVATIVES AS MODULATORS OF GLYCOSYLATION

Compounds of Formula (I) are useful as modulators of glycosylation. Compounds of Formula (I) have the following structure: (I) and the definitions of the other variables are provided herein.

Synthesis of C-spiro-glycoconjugates from sugar lactones via zinc mediated Barbier reaction

Anomeric gem-diallylation, mono-β-crotylation and mono-β- propargylation of sugar 1,5 and 1,4 lactones have been achieved under Barbier reaction conditions using Zn powder and a catalytic amount of TMSCl as an activator. Ring closing olefin metathesis of the synthesized gem-diallyl derivatives furnished C-spiro cyclopentene glycosides. Finally, the cyclopentene rings were converted into carbohydrate based tricyclic morpholine fused triazole glycoconjugates as potential SGLT2 inhibitors.