529488-04-8

Basic information

• Product Name: Trifluoro-methanesulfonic acid (2S,4S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl ester
• Synonyms: Trifluoro-methanesulfonic acid (2S,4S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl ester
• CAS NO: 529488-04-8
• Molecular Weight: 532.653
• Mol File: 529488-04-8.mol

Chemical Properties

• CAS DataBase Reference: Trifluoro-methanesulfonic acid (2S,4S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Trifluoro-methanesulfonic acid (2S,4S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl ester(529488-04-8)
• EPA Substance Registry System: Trifluoro-methanesulfonic acid (2S,4S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl ester(529488-04-8)

Safety Data

• Hazardous Substances Data: 529488-04-8(Hazardous Substances Data)

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 530112-01-7 methyl 3-O-[tert-butyl-(diphenyl)silyl]-2,4-dideoxy-D-threo-hexopyranoside 

Downstream Products

• 529488-16-2 2-(acetyloxy)-6-{(2R,4S)-4-[tert-butyl(diphenyl)silyloxy]-6-methoxytetrahydro-2H-pyran-2-ylmethyl}benzoic acid 
• 529488-09-3 {(2S,4S,6R)-2-allyl-6-[(2-methyl-1-benzofuran-4-yl)methyl]-tetrahydro-2H-pyran-4-yloxy}(tert-butyl)diphenylsilane 
• 529488-11-7 3-{(2R,4S)-4-[tert-butyl(diphenyl)silyloxy]-6-methoxytetrahydro-2H-pyran-2-ylmethyl}-2-formylphenyl acetate 
• 529488-06-0 {(4S,6R)-2-methoxy-6-[(2-methyl-1-benzofuran-4-yl)methyl]-tetrahydro-2H-pyran-4-yloxy}(tert-butyl)diphenylsilane 

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.