145401-47-4

Usage

InChI:InChI=1/C21H39NO7/c1-2-3-4-9-12-16(24)13-10-7-5-6-8-11-14-17(25)18(26)19(27)21(22,15-23)20(28)29/h11,14,17-19,23,25-27H,2-10,12-13,15,22H2,1H3,(H,28,29)/b14-11+

Upstream product

• 397870-77-8 (2S,3R,4R)-2-acetamido-3-acetoxy-2-acetoxymethyl-4-[(E,S)-1-acetoxy-10-oxohexadec-2-en-1-yl]-4-butanolide 
• 389807-42-5 (2'E,1'S,3S,4R,5R)-3-benzamido-4-hydroxy-3-hydroxymethyl-5-(1'-hydroxy-10'-oxo-hexadec-2'-en-1'-yl)-2-oxo-tetrahydrofuran 
• 344615-58-3 (2'E,1'S,3S,4R,5R)-3-benzamido-4-benzoyloxy-3-hydroxymethyl-5-(1'-hydroxymethyl-10'-oxo-hexadec-2'-en-1'-yl)-2-oxo-tetrahydrofuran 
• 357625-81-1 (3aS,6R,6aR)-3a-Hydroxymethyl-6-((E)-(S)-1-hydroxy-10-oxo-hexadec-2-enyl)-tetrahydro-furo[3,4-d]oxazole-2,4-dione 
• 1410839-94-9 (1S,2R,6R)-methyl 2-(((tert-butoxycarbonyl)oxy)methyl)-7-oxabicyclo[4.1.0]hept-3-ene-2-carboxylate 
• 1410839-93-8 (1S,2R,6R)-methyl 2-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-ene-2-carboxylate 
• 1410839-82-5 (1R,5S,6S)-5-bromo-1-(((triisopropylsilyl)oxy)methyl)-7-oxabicyclo[4.2.0]oct-2-en-8-one 
• 482315-11-7 2-hexyl-2-(6-iodohexyl)-1,3-dioxolane 
• 1410839-64-3 1-(((triisopropylsilyl)oxy)methyl)cyclohexa-2,5-dienecarboxylic acid 

Relevant academic research and scientific papers

Total synthesis of sphingofungin E and 4,5-di-epi-sphingofungin E

Total synthesis of sphingofungin E and 4,5-di-epi-sphingofungin E was achieved from an intermediate same as that of myriocin and mycestericin D via antipodal stereoselective dihydroxylations.

Stereocontrolled total synthesis of sphingofungin e

We describe herein the asymmetric total synthesis of sphingofungin E, which has potent immunosuppressive activity. Key steps include asymmetric desymmetrization by bromolactonization, stereocontrolled construction of four contiguous stereogenic centers through allylic C-H oxidation and epoxide ring opening, regioselective elongation of a dialdehyde, and Hofmann rearrangement by using PhI(OCOCF3)2. The asymmetric total synthesis of sphingofungin E, which has potent immunosuppressive activity, is described. Key steps include asymmetric desymmetrization by bromolactonization, stereocontrolled construction of four contiguous stereogenic centers through allylic C-H oxidation and epoxide ring opening, regioselective elongation of a dialdehyde, and Hofmann rearrangement by using PhI(OCOCF3) 2; TIPS = triisopropylsilyl. Copyright

A flexible common approach to α-substituted serines and alanines: Diastereoconvergent syntheses of sphingofungins E and F

A flexible common approach for the asymmetric syntheses of sphingofungins E and F is reported, with efficient use of both diastereomers of the Baylis-Hillman adduct in a stereoconvergent manner. Pronounced steric effects of the 2-substituents in diastereo

Total synthesis of (+)-myriocin and (-)-sphingofungin E from aldohexoses using overman rearrangement as the key reaction

Total synthesis starting from aldohexoses of naturally occurring α-substituted α-amino acids, (+)-myriocin (1) and (-)-sphingofungin E (2), is described. Overman rearrangement of allylic trichloroacetimidate 6E derived from D-mannose effectively generated the tetrasubstituted carbon with nitrogen, and subsequent Wittig olefination afforded the highly functionalized moiety 3 of myriocin stereoselectively. Sulfone-mediated coupling reaction of the allyl bromide 3 with C12 hydrophobic part 4 successfully constructed the carbon framework possessing E-olefin 28. Removal of the sulfone and protecting groups completed the chiral and stereoselective total synthesis of (+)-myriocin (1). A similar transformation starting from D-glucose also accomplished the total synthesis of (-)-sphingofungin E (2).

Total synthesis of sphingofungin E from D-glucose.

[reaction: see text] Total synthesis of sphingofungin E (1) is described. Overman rearrangement of an allylic trichloroacetimidate derived from diacetone-D-glucose generated tetra-substituted carbon with nitrogen, and subsequent Wittig olefination afforde

Total synthesis of sphingofungin E from D-glucose derivative

Total synthesis of sphingofungin E (1) from an already known D-glucose derivative 9 in a stereocontrolled manner is described.

gem-diacetates as carbonyl surrogates for asymmetric synthesis. Total syntheses of sphingofungins E and F

The equivalent of an asymmetric addition to a carbonyl group with a stabilized anion is accomplished by discriminating between the enantiotopic C-O single bonds of a gem-diacetate. In this way, enantioselective total syntheses of two antifugal agents, sph

Total synthesis of sphingofungin E

Total synthesis of sphingofungin E (1) using an already known D-glucose derivative as a chiral synthon is described.

The first total synthesis of sphingofungin E and the determination of its stereochemistry

The total synthesis of sphingofungin E has been realized for the first time and its absolute configurations were established. Starting from L-(+)-tartaric acid, our synthesis featured substrate-controlled asymmetric dihydroxylation, regiospecific epoxide formation and Hatakeyama reaction to construct the contiguous chiral centers in the target molecule.