331456-83-8

Upstream product

• 131087-35-9 phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 153745-68-7 phenyl 1-thio-L-rhamnopyranoside 
• 77-76-9 2,2-dimethoxy-propane 
• 1214-98-8 phenyl 1-thio-α-L-rhamnopyranose 
• 69739-34-0 t-butyldimethylsiyl triflate 

Downstream Products

• 400737-79-3 (2S,3R,4S,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3,4-diol 
• 400738-33-2 (2S,3S,4R,5S,6S)-2-Benzyloxy-5-[(2S,3R,4S,5R,6R)-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-6-methyl-3-phenylsulfanyl-tetrahydro-pyran-2-yloxy]-4,6-dimethyl-3-phenylsulfanyl-4-triethylsilanyloxy-tetrahydro-pyran 
• 400738-29-6 (2S,3S,4R,5S,6S)-2-Benzyloxy-5-[(2S,3R,4S,5R,6R)-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-6-methyl-3-phenylsulfanyl-tetrahydro-pyran-2-yloxy]-4,6-dimethyl-3-phenylsulfanyl-tetrahydro-pyran-4-ol 
• 400738-00-3 (2S,3S,4S,5R,6S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-6-phenylsulfanyl-tetrahydro-pyran 
• 400738-11-6 (2S,3S,4R,5S,6S)-2-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-3-phenylsulfanyl-tetrahydro-pyran 
• 400738-03-6 (2S,3R,4S,5S,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol 
• 400738-14-9 (2S,3S,4R,5S,6S)-6-Benzyloxy-2,4-dimethyl-5-phenylsulfanyl-tetrahydro-pyran-3,4-diol 
• 403646-68-4 4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-[4-O-(4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-β-D-mannopyranosyl)-2,3-O-isopropylidene-α-L-rhamnopyranosyl]-β-D-galactopyranoside 
• 403646-61-7 4-(4-nitrophenyl)butyl 4,6-O-benzylidene-2-O-pivaloyl-3-O-(2,3-O-isopropylidene-α-L-rhamnopyranosyl)-β-D-galactopyranoside 
• 400737-85-1 [(2S,3S,4S,5R,6S)-4-Allyloxy-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane 
• 400737-98-6 (2S,3S,4S,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-6-phenylsulfanyl-tetrahydro-pyran-4-ol 
• 400737-89-5 (2S,3R,4S,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-ol 
• 400737-93-1 (2S,3S,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-one 
• 400737-82-8 (2S,3R,4S,5S,6S)-4-Allyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol 

Relevant academic research and scientific papers

Synthesis of Cardiotonic Steroids Oleandrigenin and Rhodexin B

This article describes a concise synthesis of cardiotonic steroids oleandrigenin (7) and its subsequent elaboration into the natural product rhodexin B (2) from the readily available intermediate (8) that could be derived from the commercially available steroids testosterone or DHEA via three-step sequences. These studies feature an expedient installation of the β16-oxidation based on β14-hydroxyl-directed epoxidation and subsequent epoxide rearrangement. The following singlet oxygen oxidation of the C17 furan moiety provides access to oleandrigenin (7) in 12 steps (LLS) and a 3.1% overall yield from 8. The synthetic oleandrigenin (7) was successfully glycosylated with l-rhamnopyranoside-based donor 28 using a Pd(II)-catalyst, and the subsequent deprotection under acidic conditions provided cytotoxic natural product rhodexin B (2) in a 66% yield (two steps).

Total Synthesis of Apoptolidin: Construction of Enantiomerically Pure Fragments

A general strategy for the total synthesis of the antitumor agent apoptolidin (1) is proposed, and the chemical synthesis of the defined key building blocks (4, 5, 6, 8, and 9) in their enantiomerically pure forms is described. The projected total synthes

Synthesis of the Salmonella type E(1) core trisaccharide as a probe for the generality of 1-(benzenesulfinyl)piperidine/triflic anhydride combination for glycosidic bond formation from thioglycosides.

A synthesis of a chromogenic glycoside of the Salmonella anatum group E(1) core trisaccharide is presented in which all three glycosidic bonds, a 1,2-cis-equatorial, a 1,2-trans-axial, and a 1,2-trans-equatorial linkage representing three of the four main classes of glycosidic bond, are formed with thioglycoside donors activated under a single set of conditions by the combination of 1-(benzenesulfinyl)piperidine and trifluoromethanesulfonic anhydride. 2,3-O-Carbonyl- and 2,3-O-isopropylidene-alpha-L-rhamnopyranosyl thioglycosides are found to be highly alpha-selective rhamnosyl donors under these conditions.

The preparation of 1-tributylstannyl glycals from 1-phenylsulfonyl glycals via Ni(0)-catalysed coupling with tributylstannylmagnesium bromide

1-Phenylsulfonyl glycals undergo an easy Ni(0)-catalysed coupling with tributylstannylmagnesium bromide to give the corresponding 1-tributylstannyl glycals in good yield.

Total synthesis of apoptolidin: Part 1. Retrosynthetic analysis and construction of building blocks

No less than 30 stereogenic elements, a highly unsaturated 20-membered macrocyclic system, four carbohydrate units, and unique biological activity, make the natural occurring apoptolidin (1) a challenging synthetic target. The retrosynthetic analysis reve