22893-94-3

Upstream product

• 139326-94-6 1,2:3,4-di-O-isopropylidene-5,6-di-O-mesyl-D-mannitol 
• 77-76-9 2,2-dimethoxy-propane 
• 1590371-74-6 C₁₅H₃₀O₄Si 
• 50629-31-7 2,3:4,5-di-O-isopropylidene-D-arabinose diethyldithioacetal 
• 69-65-8 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 
• 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 

Downstream Products

• 4105-60-6 2,3-O-isopropylidene-D-threo-4-pentenose 
• 476153-92-1 (1S,2S,3R)-1-phenyl-pent-4-ene-1,2,3-triol 
• 476153-91-0 (1R,2S,3R)-1-phenyl-pent-4-ene-1,2,3-triol 
• 476153-89-6 (R)-((4R,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)(phenyl)methanol 
• 476153-90-9 (S)-((4R,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)(phenyl)methanol 
• 476153-93-2 (1S,5S,7R,8R)-8-hydroxy-7-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-one 
• 476153-94-3 (1S,5S,7S,8R)-8-hydroxy-7-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-one 
• 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 

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.