68880-92-2

Upstream product

• 105930-42-5 (2R,4aR,6S,7R,8aS)-6-Methoxy-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 
• 76-83-5 trityl chloride 
• 123474-66-8 (2R,3S,5R,6S)-2-Hydroxymethyl-6-methoxy-5-methyl-tetrahydro-pyran-3-ol 
• 101978-79-4 Methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-allopyranoside 
• 56981-18-1 Dithiocarbonic acid O-((2R,4aR,6S,7R,8R,8aS)-6-methoxy-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl) ester S-methyl ester 
• 130061-59-5 Methyl 4,6-O-benzylidene-2-deoxy-2-methyl-α-D-glucopyranoside 
• 68880-91-1 methyl 2,3-dideoxy-2-C-methyl-α-D-arabino-hexopyranoside 
• 118360-84-2 methyl 3,4-anhydro-2-deoxy-2-C-methyl-6-O-trityl-α-D-altropyranoside 
• 118360-81-9 methyl 4-bromo-2,4-dideoxy-2-C-methyl-6-O-triphenylmethyl-α-D-idopyranoside 
• 118360-83-1 methyl 2,3-anhydro-4-bromo-4-deoxy-6-O-trityl-α-D-gulopyranoside 
• 118360-82-0 methyl 2,4-dibromo-2,4-dideoxy-6-O-triphenylmethyl-α-D-idopyranoside 
• 118360-80-8 methyl 3,4-anhydro-2-O-mesyl-6-O-trityl-α-D-altropyranoside 
• 16802-89-4 methyl 2,3-di-O-mesyl-6-O-trityl-α-D-mannopyranoside 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 

Downstream Products

• 68880-93-3 (2R,5R,6S)-6-Methoxy-5-methyl-2-trityloxymethyl-dihydro-pyran-3-one 
• 129991-98-6 (2S,3R,5S,6R)-2,5-Dimethoxy-3-methyl-6-trityloxymethyl-tetrahydro-pyran 
• 105897-93-6 (2S,3R,6S)-2-Methoxy-3-methyl-5-methylene-6-trityloxymethyl-tetrahydro-pyran 
• 73679-58-0 methyl 2,3,4-trideoxy-2,4-di-C-methyl-6-O-(triphenylmethyl)-α-D-arabino-hexopyranoside 
• 79646-63-2 methyl 2,3,4-trideoxy-2,3-di-C-methyl-6-O-trityl-α-D-ribo-hexopyranoside 
• 105897-94-7 Toluene-4-sulfonic acid (1S,2R,4R)-1-(tert-butyl-dimethyl-silanyloxymethyl)-4-[1,3]dithian-2-yl-2-methyl-pentyl ester 
• 105897-94-7 Toluene-4-sulfonic acid (1S,2S,4R)-1-(tert-butyl-dimethyl-silanyloxymethyl)-4-[1,3]dithian-2-yl-2-methyl-pentyl ester 
• 145798-90-9 (2R,3S,5S,6S)-3-Benzyloxy-6-methoxy-5-methyl-2-trityloxymethyl-tetrahydro-pyran 
• 68880-93-3 methyl 2,3-dideoxy-2-C-methyl-6-O-triphenylmethyl-α-D-threo-hexopyranosid-4-ulose 
• 135066-03-4 methyl 4-O-bromoacetyl-2,3-dideoxy-2-C-methyl-6-O-triphenylmethyl-α-D-arabino-hexopyranoside 
• 187038-01-3 (2R,3R,5S,6S)-3-Benzyloxy-6-methoxy-5-methyl-2-trityloxymethyl-tetrahydro-pyran 

Relevant academic research and scientific papers

A total synthesis of FK-506

A total synthesis of FK-506 (1) is presented. The synthesis features a highly convergent approach utilizing a block coupling strategy. Top and bottom half sections of the molecule are coupled by addition of a vinyl cuprate with a spiroenone. The α-allyl aldol functionality is revealed by a reductive opening of the spiroenone system. The labile α,β-diketoamide hemiketal portion of the molecule is prepared by a late stage generation and oxidation of a masked enediol. Top and bottom half segments are themselves derived by coupling of smaller subunits, resulting in a very convergent route.

Introduction of a chiral centre on C-6 of a carbohydrate unit: Application to the synthesis of the C-2 to C-15 fragment of ionomycin

Glucose is converted into the α,β-unsaturated urono-8,4-lactone 29 using an intramolecular Wadsworth-Emmons reaction. Higher order cuprates add to the lactone to provide the C-6 substituted carbohydrate derivative with high stereoselectivity. This product can be converted into the dithiane 34b which when coupled with an appropriate epoxide yields compound 37 which contains the C-2 to C-15 fragment of ionomycin with the correct absolute stereochemistry at each asymmetric centre for conversion into ionomycin.

Total synthesis of herbimycin A

The first total synthesis of herbimycin A (1), the benzoquinoid ansamycin antibiotic, has been accomplished by coupling two segments of the aliphatic ansa-chain 2 and the aromatic chromophore 3, elucidating the absolute stereochemistry.

Studies directed towards the synthesis of immunosuppressive agent FK-506: Construction of the tricarbonyl moiety

Alkylation of a suitably functionalised dithiane precursor with L-N-(α-haloacetyl)-pipecolic acid methyl ester, followed by oxidation of the active methylene group provided an easy route to 1,2,3-tricarbonyl functionality of FK-506.

STEREOSELECTIVE TOTAL SYNTHESIS AND STEREOCHEMISTRY OF DIPLODIATOXIN, A MYCOTOXIN FROM DIPLODIA MAYDIS

The stereochemistry of diplodiatoxin has been deduced, and the assumed stereostructure has been confirmed by the synthesis using highly stereocontrolled strategy, in which the intramolecular Diels-Alder reaction of a(E, E, E)-triene is involved.

STEREOSELECTIVE SYNTHESIS OF(-)-α-MULTISTRIATIN FROM D-GLUCOSE

D-glucose was converted into (-)-α-multistriatin, the aggregation pheromone of the Europian elm bark beetle, via a highly stereoselective eighteen-step route