14440-56-3

Basic information

• Product Name: 2,3:5,6-Di-O-isopropylidene-D-mannono-1,4-lactone
• Synonyms: 2,3:5,6-Di-O-isopropylidene-D-mannono-1,4-lactone;(3aβ,6aβ)-Tetrahydro-2,2-dimethyl-6α-[(4R)-2,2-dimethyl-1,3-dioxolane-4-yl]furo[3,4-d]-1,3-dioxole-4-one;(3S)-3β,4β-(Isopropylidenebisoxy)-5β-[(R)-1,2-(isopropylidenebisoxy)ethyl]-4,5-dihydro-2(3H)-furanone;2-O,3-O:5-O,6-O-Bis(1-methylethylidene)-D-mannonic acid γ-lactone;2-O,3-O:5-O,6-O-Diisopropylidene-D-mannonic acid 1,4-lactone;2-O,3-O:5-O,6-O-Diisopropylidene-D-mannonic acid γ-lactone;2-O,3-O:5-O,6-O-Diisopropylidene-D-mannonic acid-1,4-lactone;2,3:5,6-Di-O-isopropylidene-D-mannonic acid-1,4-lactone
• CAS NO: 14440-56-3
• Molecular Formula: C₁₂H₁₈O₆
• Molecular Weight: 258.27
• Mol File: 14440-56-3.mol
• Article Data: 35

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,3:5,6-Di-O-isopropylidene-D-mannono-1,4-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3:5,6-Di-O-isopropylidene-D-mannono-1,4-lactone(14440-56-3)
• EPA Substance Registry System: 2,3:5,6-Di-O-isopropylidene-D-mannono-1,4-lactone(14440-56-3)

Safety Data

• Hazardous Substances Data: 14440-56-3(Hazardous Substances Data)

Usage

General Description

2,3:5,6-Di-O-isopropylidene-D-mannono-1,4-lactone is a chemical compound that is often used in organic synthesis and as a building block for other molecules. It is a lactone derivative of D-mannose and is known for its ability to act as a protecting group for the hydroxyl group in carbohydrates. 2,3:5,6-Di-O-isopropylidene-D-mannono-1,4-lactone is commonly utilized in the synthesis of complex natural products and pharmaceuticals due to its role as a versatile intermediate. Additionally, it can be used in the modification of sugars and other natural products to alter their properties. Its unique structure and reactivity make it an important chemical in the field of organic chemistry.

Upstream product

• 14131-84-1 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 
• 77-76-9 2,2-dimethoxy-propane 
• 26301-79-1 D-mannono-1,4-lactone 
• 40036-82-6 [2,3:5,6]-di-O-isopropylidene-D-mannose 
• 3458-28-4 D-Mannose 
• 1128-23-0 L-gulonolactone 
• 7757-38-2 O²,O³,O⁵,O⁶-diisopropylidene D-mannofuranose 
• 67-64-1 acetone 
• 530-26-7 D-Mannose 
• 95517-29-6 1-C-nitroso-2,3:5,6-di-O-isopropylidenemannofurasonyl chloride 
• 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 
• 131444-81-0 5-O-acetyl-1,2-dideoxy-3,4:6,7-di-O-isopropylidene-D-manno-hept-1-enitol 
• 89-65-6 isoascorbic acid 

Downstream Products

• 445412-03-3 (3aS,6S,6aS)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one O-benzyl-oxime 
• 1346258-10-3 1-bromo-9-O-[(t-butyl)diphenylsilyl]-1,2,3-trideoxy-D-glycero-D-galacto-1-yno-nonitol 
• 1346258-12-5 4-O-[(t-butyl)diphenylsilyl]-1,2,3-trideoxy-5,6:8,9-di-O-isopropylidene-D-glycero-D-galacto-1-yno-nonitol 
• 153666-19-4 ketodeoxynonulosonic acid 
• 138034-65-8 (1R)-2,3-5,6-di-O-isopropylidene-1-C-phenyl-D-mannitol 
• 138034-65-8 (R)-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)((4S,5R)-5-((S)-hydroxy (phenyl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol 
• 1415325-89-1 (1S)-2,3:5,6-di-O-isopropylidene-1-C-phenyl-D-talitol 
• 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 
• 1415308-12-1 (R)-1-((3aS,4R,6R,6aR)-2,2-dimethyl-6-phenyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)ethane-1,2-diol 
• 1415308-13-2 C-phenyl 2,3:5,6-di-O-isopropylidene-α-d-talofuranoside 

Relevant articles and documents

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

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.

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.

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.

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.