3969-59-3

Basic information

• Product Name: 1,2:3,4:5,6-TRI-O-ISOPROPYLIDENE-D-MANNITOL
• Synonyms: MANNITOL TRIACETONATE;1,2:3,4:5,6-TRI-O-ISOPROPYLIDENE-D-MANNITOL;1,2,3:4,5,6-O-Triisopropylidene-D-mannitol;1-O,2-O:3-O,4-O:5-O,6-O-Triisopropylidene-D-mannitol;1-O,2-O:3-O,4-O:5-O,6-O-Tris(1-methylethylidene)-D-mannitol;(4R,5R)-4,5-bis[(4R)-2,2-Dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolane
• CAS NO: 3969-59-3
• Molecular Formula: C₁₅H₂₆O₆
• Molecular Weight: 302.36
• Mol File: 3969-59-3.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 342.8 °C at 760 mmHg
• Flash Point: 132.2 °C
• Appearance: /
• Density: 1.099 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.459
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1,2:3,4:5,6-TRI-O-ISOPROPYLIDENE-D-MANNITOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2:3,4:5,6-TRI-O-ISOPROPYLIDENE-D-MANNITOL(3969-59-3)
• EPA Substance Registry System: 1,2:3,4:5,6-TRI-O-ISOPROPYLIDENE-D-MANNITOL(3969-59-3)

Safety Data

• Hazardous Substances Data: 3969-59-3(Hazardous Substances Data)

Usage

General Description

1,2:3,4:5,6-Tri-O-isopropylidene-D-mannitol, or TIPM, is a highly specialized organic compound, composed predominantly of carbon, hydrogen, and oxygen. It is a derivative of D-mannitol, a type of sugar alcohol found naturally in fruits and vegetables. The isopropylidene groups that TIPM gets its name from are moieties characterized by two carbon atoms double-bonded to the same oxygen atom. In the context of TIPM, these groups serve to protect the hydroxyl (or -OH) groups on the D-mannitol molecule. This chemical is widely used in research and development processes within the pharmaceutical industry due to its properties and versatility. Overall, it is a compound of significant importance within scientific research and practical applications.

InChI:InChI=1/C15H26O6/c1-13(2)16-7-9(18-13)11-12(21-15(5,6)20-11)10-8-17-14(3,4)19-10/h9-12H,7-8H2,1-6H3/t9-,10-,11-,12-/m1/s1

Upstream product

• 50-70-4 D-glucitol 
• 67-64-1 acetone 
• 4306-35-8 1,2-O-isopropylidene-D-glucitol 
• 69-65-8 mannitol 
• 116-11-0 2-Methoxypropene 
• 77-76-9 2,2-dimethoxy-propane 

Downstream Products

• 73346-74-4 (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol 
• 81546-82-9 9-((2S,3S)-threo-2,3-O-isopropylidene-4-O-p-toluenesulfonyl-2,3,4-trihydroxybutyl)adenine 
• 69434-38-4 Benzoic acid (4R,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 
• 81738-98-9 C₂₁H₂₂O₆ 
• 69434-40-8 (4R,5R)-2,2-dimethyl-4-benzoyloxymethyl-5-p-toluenesulfonyloxymethyl-1,3-dioxolane 
• 51064-65-4 1,4-di-o-tosyl-2,3-isopropylidene-D-threitol 
• 346588-20-3 1-O-benzyl-2,3-O-(1-methylethylidene)-D-arabinitol 
• 111765-92-5 (2S,3R,4R)-N-(benzyloxycarbonyl)-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidine 
• 19139-73-2 (4S,4’R,5R)-5-[(benzyloxy)methyl]-2,2,2’,2’-tetramethyl-4,4’-bis[1,3-dioxolane] 
• 19713-95-2 (2S,3R,4R)-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidine 
• 19139-74-3 2,3:4,5-di-O-isopropylidene-D-arabinitol 
• 869660-98-0 (2R,3R,4S)-1-O-benzyl-4-(tert-butoxycarbonyl)amino-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentane-1,2,3-triol 
• 1053622-69-7 Methanesulfonic acid (4R,5R)-5-[(S)-1-tert-butoxycarbonylamino-2-(4-methoxy-phenyl)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 
• 869660-99-1 (2R,3R,4S)-4-(tert-butoxycarbonyl)amino-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentane-1,2,3-triol 

Relevant articles and documents

Mild and facile procedure for clay-catalyzed acetonide protection and deprotection of N(Boc)-amino alcohols and protection of 1,2-diols

The application of clay as a catalyst for acetonide protection of N(Boc)-amino alcohols and 1,2-diols to obtain good to excellent yields of the acetonide derivatives is described. Acetonide deprotection to obtain the parent amino alcohol was carried out using a similar catalyst in the presence of methanol as solvent. The reaction takes place at room temperature within 2h to give the parent amino alcohol in quantitative yield keeping the N(Boc) group intact.

Synthesis of 2,3-O-Isopropylidene-D-glyceraldehyde in High Chemical and Optical Purity: Observations on the Development of a Practical Bulk Process

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THE SYNTHESIS OF 1,2:5,6-DI-O-ISOPROPYLIDENE-D-MANNITOL: A COMPARATIVE STUDY

Three different methods of acetonation of D-mannitol using (a) acetone and zinc chloride, (b) 2,2-dimethoxypropane, 1,2-dimethoxyethane, and tin(II)chloride, and (c) 2-methoxypropane, N,N-dimethylformamide, and p-toluenesulfonic acid were studied in detail and compared, using gas-liquid chromatographic techniques.In each reaction, isomeric diacetals are formed, but method a gives the 1,2:5,6-diacetal in the highest yield (63percent).Methods b and c give a more complex mixture of acetals than proposed in the literature, and both methods are less economical than a.A new 1,2:3,6:4,5-tri-O-isopropylidene-D-mannitol could be separated, and its graded hydrolysis was compared to that of the 1,2:3,4:5,6-triacetal.