131156-54-2

Upstream product

• 58871-09-3 6-O-tert-butyldimethylsilyl-D-glucal 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 13265-84-4 D-glucal 

Downstream Products

• 529488-03-7 2,6-anhydro-1-O-[tert-butyl(dimethyl)silyl]-4-O-[tert-butyl-(diphenyl)silyl]-3,5-dideoxy-D-threo-hex-5-enitol 
• 529488-02-6 1,5-anhydro-6-O-[tert-butyl(dimethyl)silyl]-3-O-[tert-butyl-(diphenyl)silyl]-2-deoxy-4-O-(1H-imidazol-1-ylthiocarbonyloxy)-D-arabino-hex-1-enitol 

Relevant academic research and scientific papers

A formal total synthesis of (+)-apicularen A: Base-induced conversion of apicularen-derived intermediates into salicylihalamide-like products

A synthesis of apicularen precursor (-)-6 in 18 steps from D-glucal is reported. As (+)-6 has been converted into the potent, naturally occurring salicylate anti-cancer agent, (-)-apicularen A in 8 steps, this study constitutes a formal total synthesis of (+)-apicularen A. Key steps in the synthetic route include: (i) useful D-glucal elaboration processes. (ii) organometallic displacements at carbohydrate C-6 triflates using Knochel-type and related functionalised, aromatic Grignard reagents, (iii) stereoselective allyltrimethylsilane-acetal reactions generating C-allyl systems. (iv) stereocontrolled aldehyde allylation processes from both substrate and reagent, and (v) a novel Keck-type macrolactonisation. In addition, preliminary studies are reported in which a procedure has been devised to convert apicularen-derived intermediates into salicylihalamide-like products.

SELECTIVE CLEAVAGE OF t-BUTYLDIPHENYLSILYL ETHERS IN THE PRESENCE OF t-BUTYLDIMETHYLSILYL ETHERS

The rate of cleavage of t-butyldiphenylsilyl (TBDPS) ethers with sodium hydride in hexamethylphosphoric triamide (HMPA) is significantly faster than that of the corresponding t-butyldimethylsilyl (TBDMS) ethers.The TBDPS ethers can be selectively cleaved