4239-90-1

Usage

Diisopropylidene groups at positions 1,2 and 3,4

1-O,2-O:3-O,4-O-Diisopropylidene-5,6-dideoxy-5,6-didehydro-D-mannitol 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

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

Downstream Products

• 30377-02-7 (Ξ)-3-(4-nitro-phenyl)-5-((4R,4'R)-2,2,2',2'-tetramethyl-(4rH)-tetrahydro-[4,4']bi[1,3]dioxolyl-5c-yl)-4,5-dihydro-isoxazole 
• 123672-31-1 (2R,3S,4R)-hex-5-ene-1,2,3,4-tetraol 
• 792915-37-8 (R)-2-Benzyloxy-2-((4S,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-ethanol 
• 792915-38-9 (E)-(R)-5-Benzyloxy-5-((4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-pent-3-en-2-one 
• 792915-36-7 [(R)-2-Benzyloxy-2-((4S,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-ethoxy]-tert-butyl-dimethyl-silane 
• 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 

Relevant academic research and scientific papers

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.

Stereoselective Total Synthesis of (+)-Anamarine and 8- epi -(-)-Anamarine from D-Mannitol

Stereoselective total synthesis of (+)-anamarine and the first synthesis of 8-epi-(-)-anamarine, its nonnatural diastereomer, were achieved from readily available d-mannitol. The key reactions involved were asymmetric dihydroxylation, cross-metathesis and ring-closing metathesis reactions. The approach is adoptable advantageously for the diversity-oriented synthesis of several related classes of natural products.

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.

Toward synthesis of carbasugars (+)-gabosine C, (+)-COTC, (+)-pericosine B, and (+)-pericosine C

Asymmetric total synthesis of (+)-gabosine C, (+)-pericosine B, and (+)-pericosine C has been reported from readily available d-(-)-isoascorbic acid and d-ribose involving Grubbs ring closing metathesis, Morita-Baylis-Hillman (MBH) reaction, and Luche red

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.

An efficient synthesis of synargentolide A from D-mannitol

An efficient synthesis of synargentolide A is described by using d-mannitol and d-malic acid. The key features of the synthetic strategy include Wittig olefination, ring closing-metathesis reaction and cross-metathesis reaction for the formation of synarg

Stereoselective and facile total synthesis of (+)-goniodiol, a styryllactone from carbohydrates

The stereoselective synthesis of (+)-goniodiol, a cytotoxic styryllactone, has been accomplished in 10 steps starting from inexpensive and readily available d-manitol and δ-gluconolactone involving the direct and straightforward reaction conditions of Gri

Total syntheses of (+)-7-epi-goniofufurone, (+)-goniopypyrone and (+)-goniofufurone from a common precursor

Total syntheses of (+)-7-epi-goniofufurone, (+)-goniopypyrone and (+)-goniofufurone have been achieved from an advanced common precursor formed from d-(+)-mannitol by changing the carbinol protection profile. The Royal Society of Chemistry.

Synthesis of (+)-goniothalesdiol and (+)-7-epi-goniothalesdiol

A total synthesis of (+)-goniothalesdiol, a 3,4-dihydroxy-2,5-disubstituted tetrahydrofuran isolated from Goniothalamus borneensis (Annonaceae), and its 7-epimer is reported using oxycarbonylation methodology for construction of polyhydroxylated substitut

A chiron approach to (1R,2R,5S,7R)-2-hydroxy-exo-brevicomin, a component of the volatiles produced by the male mountain pine beetle, Dendroctonus ponderosae

A chiron approach to a synthesis of (1R,2R,5S,7R)-2-hydroxy-exo-brevicomin 1, a component of the volatiles obtained from male mountain pine beetles, Dendroctonus ponderosae has been achieved. Our synthesis started with commercially available d-mannitol and involved Wittig olefination, acid catalysed one-pot hydrogenation and internal acetalization as key steps.