4239-90-1

Basic information

• Product Name: 1-O,2-O:3-O,4-O-Diisopropylidene-5,6-dideoxy-5,6-didehydro-D-mannitol
• Synonyms: 1-O,2-O:3-O,4-O-Diisopropylidene-5,6-dideoxy-5,6-didehydro-D-mannitol;3-O,4-O:5-O,6-O-Diisopropylidene-1,2-dideoxy-D-arabino-1-hexenitol;3-O,4-O:5-O,6-O-Diisopropylidene-1,2-dideoxy-D-arabino-hexa-1-enitol
• CAS NO: 4239-90-1
• Molecular Formula: C₁₂H₂₀O₄
• Molecular Weight: 228.2848
• Mol File: 4239-90-1.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-O,2-O:3-O,4-O-Diisopropylidene-5,6-dideoxy-5,6-didehydro-D-mannitol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-O,2-O:3-O,4-O-Diisopropylidene-5,6-dideoxy-5,6-didehydro-D-mannitol(4239-90-1)
• EPA Substance Registry System: 1-O,2-O:3-O,4-O-Diisopropylidene-5,6-dideoxy-5,6-didehydro-D-mannitol(4239-90-1)

Safety Data

• Hazardous Substances Data: 4239-90-1(Hazardous Substances Data)

Usage

Diisopropylidene groups at positions 1,2 and 3,4

This compound has two isopropyl groups (a group composed of three carbon atoms) connected to the molecule at positions 1,2 and 3,4, which contribute to its complexity and reactivity.

Dideoxy and didehydro functionalities at positions 5,6

The molecule has two oxygen atoms removed from the sugar ring at positions 5 and 6, and two hydrogen atoms are added in their place, resulting in the formation of a double bond. This gives the compound unique chemical properties.

Used in organic synthesis and chemical research

Due to its complex structure and unique reactivity, the compound is commonly used in organic synthesis and chemical research to develop new chemical processes and elucidate complex reaction mechanisms.

Building block in the synthesis of more complex molecules and pharmaceuticals

The compound is also used as a starting material or building block in the synthesis of more complex molecules and pharmaceuticals.

Upstream product

• 69-65-8 mannitol 
• 50629-31-7 2,3:4,5-di-O-isopropylidene-D-arabinose diethyldithioacetal 
• 1590371-74-6 C₁₅H₃₀O₄Si 
• 77-76-9 2,2-dimethoxy-propane 
• 38145-93-6 (S)-1-((4R,4'R,5R)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)ethane-1,2-diol 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 13039-93-5 2,2:4,5-di-O-isopropylidene-D-arabinose 
• 3969-59-3 mannitol triacetonide 
• 38145-93-6 1,2:3,4-di-O-isopropylidene-D-mannitol 
• 139326-94-6 1,2:3,4-di-O-isopropylidene-5,6-di-O-mesyl-D-mannitol 

Downstream Products

• 1392302-09-8 (4S,4'R,5R)-5-(2-(benzyloxy)ethyl)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolane) 
• 1392302-10-1 (R)-1-((4R,5R)-5-(2-(benzyloxy)ethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1,2-diol 
• 1392302-11-2 (R)-1-((4R,5R)-5-(2-(benzyloxy)ethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol 
• 1392302-12-3 ((R)-1-((4S,5R)-5-(2-(benzyloxy)ethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethoxy)(tert-butyl)dimethylsilane 
• 104121-92-8 Eldecalcitol 
• 342644-90-0 [3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-hydroxy-2-methylenecyclohexylidene]ethyl trimethylacetate 
• 1424750-75-3 (2R,3S,4R)-2,3,4-O-tibenzoyl-5-deoxy-5-bromo-D-arabinose 
• 1424750-72-0 (2R,3S,4R)-2,3,4-O-tribenzoyl-1-bromo-2,3,4-hex-5-enetriol 

Relevant articles and documents

Structural revisions of the reported A-ring phosphine oxide synthon for ED-71 (Eldecalcitol) and a new synthesis

In a reported procedure for the synthesis of the ED-71 A-ring phosphine oxide, we discovered that unusual TBS transfer occurred from the 1α-position to the sterically more constrained 2β-position, and the subsequent Michael addition of ethyl acrylate predominated at the 1α-position. The X-ray analysis of a key intermediate confirmed our observations. We made a structural revision of the reported A-ring phosphine oxide synthon and ED-71. In addition, we provided the first stereoselective synthetic approach to ED-71 A-ring phosphine oxide applying the stereochemistry of d-mannitol.

Synthesis of vicinal diketoses by using a metathesis-hydroxylation-oxidation sequence

Symmetrical vicinal diuloses were prepared from 2,3:4,5-di-O-isopropylidene-D-arabinose and-L-arabinose by using methyltriphenylphosphonium bromide to convert both enantiomers into the corresponding 1,2-dideoxy-3,4:5,6-di-O-isopropylidene-arabino-hex-1-enitols D-5 and L-5. The metathesis reactions of D-5 with itself and with L-5, respectively, by using the Hoveyda-Grubbs catalyst gave diastereomeric dec-5-enitols DD-6 and DL-6, which were dihydroxylated with osmium tetroxide to give 1,2:3,4:7,8:9,10-tetra-O-isopropylidene-protected decitols DD-7 and DL-7. Swern oxidation of the decitols afforded isopropylidene-protected deco-5,6-diuloses DD-8 and DL-8, which gave unprotected deco-5,6-diuloses DD-9 and DL-9 upon acidic cleavage of the isopropylidene groups. The structures of both diastereomers were confirmed by NMR spectroscopy and X-ray crystal structure analysis.

Total synthesis of (+)-synargentolide A

The highly stereoselective total synthesis of polyacetate α,β-unsaturated δ-lactone natural product (+)-synargentolide A has been accomplished from inexpensive d-1,5-gluconolactone. Key reactions involved in the synthesis are hydroboration, Wittig olefination, Brown's asymmetric allylation, and a ring closing metathesis reaction. 2012 Elsevier Ltd.