131156-54-2

Basic information

• Product Name: (2R,3R,4R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(tert-butyl-diphenyl-silanyloxy)-3,4-dihydro-2H-pyran-3-ol
• Synonyms: (2R,3R,4R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(tert-butyl-diphenyl-silanyloxy)-3,4-dihydro-2H-pyran-3-ol
• CAS NO: 131156-54-2
• Molecular Weight: 498.81
• Mol File: 131156-54-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2R,3R,4R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(tert-butyl-diphenyl-silanyloxy)-3,4-dihydro-2H-pyran-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(tert-butyl-diphenyl-silanyloxy)-3,4-dihydro-2H-pyran-3-ol(131156-54-2)
• EPA Substance Registry System: (2R,3R,4R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(tert-butyl-diphenyl-silanyloxy)-3,4-dihydro-2H-pyran-3-ol(131156-54-2)

Safety Data

• Hazardous Substances Data: 131156-54-2(Hazardous Substances Data)

Upstream product

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

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 articles and documents

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.