70147-48-7

Basic information

• Product Name: 2C-Hydroxymethyl-2,3:5,6-di-O-isopropylidene-D-mannono-1,4-lactone
• Synonyms: 2C-Hydroxymethyl-2,3:5,6-di-O-isopropylidene-D-mannono-1,4-lactone;2-C-(Hydroxymethyl)-2,3:5,6-bis-O-(1-methylethylidene)-D-mannonic acid gamma-lactone
• CAS NO: 70147-48-7
• Molecular Formula: C13H20O7
• Molecular Weight: 288.294
• Mol File: 70147-48-7.mol

Chemical Properties

• Melting Point: 130-132 °C
• Boiling Point: 415.1±45.0 °C(Predicted)
• Appearance: /
• Density: 1.268±0.06 g/cm3(Predicted)
• PKA: 13.85±0.10(Predicted)
• CAS DataBase Reference: 2C-Hydroxymethyl-2,3:5,6-di-O-isopropylidene-D-mannono-1,4-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: 2C-Hydroxymethyl-2,3:5,6-di-O-isopropylidene-D-mannono-1,4-lactone(70147-48-7)
• EPA Substance Registry System: 2C-Hydroxymethyl-2,3:5,6-di-O-isopropylidene-D-mannono-1,4-lactone(70147-48-7)

Safety Data

• Hazardous Substances Data: 70147-48-7(Hazardous Substances Data)

Upstream product

• 57-48-7 D-Fructose 
• 143-33-9 sodium cyanide 
• 67-64-1 acetone 
• 7757-38-2 2,3,5,6-di-O-isopropylidene-D-mannofuranose 
• 773837-37-9 sodium cyanide 
• 87-81-0 D-tagatose 
• 14131-84-1 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 

Downstream Products

• 211623-13-1 (3aS,6R,6aS)-3a-((benzyloxy)methyl)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one 

Relevant articles and documents

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C-branched iminosugars: α-glucosidase inhibition by enantiomers of isoDMDP, isoDGDP, and isoDAB- l -isoDMDP compared to miglitol and miglustat

The Ho crossed aldol condensation provides access to a series of carbon branched iminosugars as exemplified by the synthesis of enantiomeric pairs of isoDMDP, isoDGDP, and isoDAB, allowing comparison of their biological activities with three linear isomeric natural products DMDP, DGDP, and DAB and their enantiomers. l-IsoDMDP [(2S,3S,4R)-2,4-bis(hydroxymethyl)pyrrolidine-3,4-diol], prepared in 11 steps in an overall yield of 45% from d-lyxonolactone, is a potent specific competitive inhibitor of gut disaccharidases [Ki 0.081 μM for rat intestinal maltase] and is more effective in the suppression of hyperglycaemia in a maltose loading test than miglitol, a drug presently used in the treatment of late onset diabetes. The partial rescue of the defective F508del-CFTR function in CF-KM4 cells by l-isoDMDP is compared with miglustat and isoLAB in an approach to the treatment of cystic fibrosis.

Doubly carbon-branched pentoses: synthesis of both enantiomers of 2,4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose using only acetonide protection

An acetonide is the only protecting group used in the synthesis of both the enantiomers of 2,4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose via the enantiomeric 3-C-methyl-l-erythronolactone [from 2-C-methyl-d-ribono-lactone or d-ribose] and 3-C-methyl-d-erythronolactone [from d-tagatose or l-ribose]. NMR studies on unprotected C-methyl arabinoses show that methyl branching significantly affects the ratios of pyranose and furanose forms present in aqueous solution.

Kiliani on ketoses: Branched carbohydrate building blocks from D-fructose and L-sorbose

Protected branched sugar lactones are available via Kiliani-acetonation sequences on readily available ketoses such as d-fructose and l-sorbose. In both cases, the readily crystallized diacetonides have a 2,3-cis-diol relationship in the product lactone. An efficient double inversion of the configuration at C-4 and C-5 of the product from d-fructose gives access to the formal Kiliani product from l-psicose. Branched carbohydrate lactones are likely to be of significant value as chirons for homochiral targets with functionalized quaternary centres.