184691-06-3

Upstream product

• 184691-05-2 (2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxy)-2-methoxymethoxy-butyraldehyde 
• 115869-43-7 (tert-butyldiphenylsilanyloxy)acetaldehyde 
• 184691-04-1 C₃₀H₄₈O₄Si₂ 
• 184691-03-0 (E)-(2R,3S)-1-(tert-Butyl-diphenyl-silanyloxy)-3-methoxymethoxy-hex-4-en-2-ol 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 138499-16-8 2-[(tert-butyldiphenylsilyl)oxy]ethanol 

Downstream Products

• 184691-07-4 C₄₄H₈₀O₆Si₄ 
• 184691-08-5 (2S,3R,4R,5R)-2,3,5-Tris-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-4-methoxymethoxy-hexanal 
• 184691-09-6 (2R,3R,4R,5R)-2,3,5-Tris-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-4-methoxymethoxy-hexan-1-ol 

Relevant academic research and scientific papers

Synthesis of Chiral α,δ-Dioxygenated Allylic Stannanes as Reagents for Carbohydrate Synthesis and Homologation

The oe-oxygenated allylic stannanes 4.4 and 4.5, prepared through addition of Bu3SnLi to γ-OTBS crotonaldehyde 4.3c followed by etherification of the adduct with TBS-C1 or MOM-C1, undergo transmetalation with InCls and in situ addition to aldehydes leading to mainly anti adducts 5.1 or 5.2, accompanied by varying amounts of syn diastereomers. Selectivities of >95:5 can be realized with the MOM reagent 4.5 and ynals 4.3d and 4.3e or cyclohexanecarboxaldehyde 4.3a. With enals 4.3b and 4.3c, 80:20 mixtures of anti and syn adducts are formed. The S enantiomer 10.1 of stannane 4.5 has also been prepared as a reagent for carbohydrate synthesis. Accordingly, addition to ct-ODPS acetaldehyde 10.2 in the presence of InCl3 leads to the adduct 10.3 as an inseparable 90:10 mixture of anti and syn diastereomers. Dihydroxylation of the OTBS derivative 10.4 affords the potential altrose precursor 10.5 in 81% yield.