37836-36-5

Upstream product

• 162473-10-1 N-[(4aR,7R,7aR)-2,2-Dimethyl-5-oxo-7-((E)-10-oxo-hexadec-2-enyl)-dihydro-furo[3,4-d][1,3]dioxin-4a-yl]-benzamide 
• 1054637-94-3 (S)-2-Benzoylamino-2-{(4R,5R)-5-[2-(4-methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-3-methoxymethoxy-propionic acid 
• 158356-08-2 (S)-2-Benzoylamino-2-{(4R,5R)-5-[2-(4-methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-3-methoxymethoxy-propionic acid methyl ester 
• 158356-07-1 N-((S)-1-Formyl-1-{(4R,5R)-5-[2-(4-methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-ethyl)-benzamide 
• 158356-06-0 N-((S)-1-Hydroxymethyl-1-{(4R,5R)-5-[2-(4-methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-ethyl)-benzamide 
• 158356-13-9 N-[(3S,4R,5R)-4-Hydroxy-3-hydroxymethyl-2-oxo-5-((Z)-10-oxo-hexadec-2-enyl)-tetrahydro-furan-3-yl]-benzamide 
• 497227-92-6 (3aS,6R,6aR)-6-((E)-3-Iodo-allyl)-3a-methoxymethoxymethyl-2-phenyl-6,6a-dihydro-3aH-furo[3,4-d]oxazol-4-one 

Downstream Products

• 38223-42-6 (3aS)-2-(4-bromo-phenyl)-3a-hydroxymethyl-6t-(10-oxo-hexadec-2t-enyl)-(3ar,6ac)-6,6a-dihydro-3aH-furo[3,4-d]oxazol-4-one 
• 38223-43-7 (3aS)-3a-acetoxymethyl-2-(4-bromo-phenyl)-6t-(10-oxo-hexadec-2t-enyl)-(3ar,6ac)-6,6a-dihydro-3aH-furo[3,4-d]oxazol-4-one 
• 88278-43-7 5-benzoylamino-5-benzoyloxymethyl-2,5-dideoxy-4-O-benzoyl-D-mannurono-3,6-lactone 

Relevant academic research and scientific papers

Construction of Quaternary Carbon Stereocenter of α-Tertiary Amine through Remote C-H Functionalization of Tris Derivatives: Enantioselective Total Synthesis of Myriocin

We describe the development of a strategy for the construction of the quaternary carbon stereocenter of α-tertiary amines. This strategy highlights a site-selective C-H functionalization involving an alkoxy-radical-triggered 1,5-hydrogen transfer (1,5-HAT

Total synthesis of myriocin and mycestericin D employing Rh(II)-catalyzed C[sbnd]H amination followed by stereoselective alkylation

Total synthesis of myriocin and mycestericin D was achieved using the Du Bois Rh(II)-catalyzed C[sbnd]H amination of a sulfamate and subsequent alkylation as a key step. The reaction of a sulfamate with PhI(OAc)2and MgO in the presence of Rh2(OAc)4gave oxathiazinane N,O-acetal as the sole product in high yield. Alkylation of N,O-acetal using vinylmagnesium bromide in the presence of ZnCl2proceeded stereoselectively to provide an oxathiazinane bearing a quaternary chiral center in high yield. Myriocin and mycestericin D were synthesized from a common synthetic intermediate. This route includes the first application of the Du Bois procedure for constructing a quaternary chiral center.

Stereocontrolled total synthesis of (-)-myriocin

The stereocontrolled total synthesis of (-)-myriocin 1 is reported. Optically active epoxide 9 was converted from symmetrical cyclohexadiene 8, utilizing an enzymatic kinetic resolution. The three sequential stereogenic centers of 1 were constructed by a regioselective epoxide-opening reaction and a Hofmann rearrangement. Elongation of the side chain was efficiently accomplished by the Julia-Kocienski reaction.

Total synthesis of the immunosuppressants myriocin and 2-epi-myriocin

(Chemical Equation Presented) Total syntheses of the natural immunosuppressant myriocin (1) and the equipotent unnatural analogue 2-epi-myriocin (in protected form) have been achieved through a common strategy. The key transformations are the efficient synthesis of a quaternary (E)-vinylglycine by asymmetric deconjugative alkylation of a dehydroamino acid and an unusually highly diastereoselective dihydroxylation of the vinylglycine alkene.

Total synthesis of myriocin

A concise, stereocontrolled synthesis of myriocin was achieved. Key features involve diastereoselective oxazoline formation catalyzed by palladium(0), MgBr2-promoted allylic stannane addition, and palladium(0)-catalyzed coupling of a vinyl iodide with an organozinc reagent.

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).

Stereoselective total synthesis of (+)-myriocin from D-mannose

The stereoselective total synthesis of myriocin 1 from D-mannose is described; the carbon framework with three contiguous chiral centers including a tetra-substituted carbon with nitrogen was effectively constructed using Overman rearrangement as the key

A novel enantioselective synthesis of (+)-myriocin based on the chemistry of 1-trimethylsilylbuta-2,3-dienes

A synthesis of (+)-myriocin has been achieved in a highly stereoselective manner employing TiCl4 catalyzed addition of 1- trimethylsilylbuta-2,3-diene to an aldehyde and Et2AICI catalysed cyclization of an epoxytrichloroacetimidate f

Total Syntheses of Myriocin and Z-Myriocin, Two Potent Immunosuppressants, from 2-Deoxy-D-Glucose

Total syntheses of myriocin (thermozymocidin, ISP-1, 21) and its analog, Z-myriocin (22), which showed potent immunosuppressive activity, were accomplished starting from 2-deoxy-D-glucose by employing a modified Darzen reaction as a key reaction.The stereoselectivity of the modified Darzen reaction for six-membered cyclic ketones was discussed on the basis of physicochemical evidence including the conformational analyses of the cyclic ketones based on molecular mechanics calculation.

Asymmetric Total Synthesis of ISP-I (Myriocin, Thermozymocidin), a Potent Immunosuppressive Principle in the Isaria sinclairii Metabolite

Asymmetric total synthesis of ISP-I has been achived by utilizing highly selectrive E-olefin formation based on the Schlosser-modified Wittig reaction and highly diastereoselective aldol reactions employing both chiral heterocyclic derivatives, 3-acetyl-(4S)-isopropyl-1,3-thiazolidine-2-thione and ethyl -2-yl carboxylate.