106357-31-7

Upstream product

• 79027-28-4 (2S)-3-(benzyloxy)-2-methylpropanal 
• 106357-20-4 (R,R)-diisopropyl tartrate (Z)-crotylboronate 
• 99687-40-8 (R,R)-[(E)-2-butenyl]diisopropyl tartrate boronate 
• 106357-33-9 (4S,5S)-2-[(2Z)-2-butenyl]-1,3,2-dioxaborolane-4,5-dicarboxylic acid bis(1-methylethyl) ester 
• 99397-92-9 (Z)-(-)-crotylbis(isopinocampheyl)borane 
• 99438-30-9 (Z)-(+)-crotyldiisopinocampheyl borane 
• 100-39-0 benzyl bromide 
• 108867-45-4 (2S,3S,4R)-2,4-dimethyl-hex-5-ene-1,3-diol 
• 63930-49-4 (R)-3-(benzyloxy)-2-methylpropan-1-ol 

Downstream Products

• 220691-93-0 (3R,4S,5S)-6-Benzyloxy-3,5-dimethyl-hexane-1,4-diol 
• 1250255-92-5 (2S,3S,4R)-1-benzyloxy-2,4-dimethyl-3-triethylsilyloxyhex-5-ene 
• 131589-19-0 (2S,3R,4R,5S)-1-O-benzyl-3-O-(tert-butyldimethylsilyl)-2,4,6-trimethyl-6-heptene-1,3,5-triol 
• 131681-61-3 (2S,3R,4R,5R)-1-O-benzyl-3-O-(tert-butyldimethylsilyl)-2,4,6-trimethyl-6-heptene-1,3,5-triol 
• 131681-73-7 (2S,3R,4S,5R,6R,7S,10S,11R,12R,13R)-1,11-di-O-benzyl-13-O-(tert-butyldimethylsilyl)-2,4,6,8,10,12-hexamethyl-3,5-O-isopropylidene-7-(thiophenoxy)-8(E)-pentadecene-1,3,5,6,11,13-hexol 
• 131589-27-0 (2S,3R,4S,5R,6R,7R,10S,11R,12R,13R)-1,11-di-O-benzyl-13-O-(tert-butyldimethylsilyl)-2,4,6,8,10,12-hexamethyl-3,5-O-isopropylidene-7-(thiophenoxy)-8(E)-pentadecene-1,3,5,6,11,13-hexol 
• 131681-74-8 (2S,3R,4S,5R,6S,7S,10S,11R,12R,13R)-1,11-di-O-benzyl-13-O-(tert-butyldimethylsilyl)-2,4,6,8,10,12-hexamethyl-3,5-O-isopropylidene-7-(thiophenoxy)-8(E)-pentadecene-1,3,5,6,11,13-hexol 
• 131681-65-7 (2S,3R,4S,5R,6S,7R,10S,11R,12R,13R)-1,11-di-O-benzyl-13-O-(tert-butyldimethylsilyl)-2,4,6,8,10,12-hexamethyl-3,5-O-isopropylidene-7-(thiophenoxy)-8(E)-pentadecene-1,3,5,6,11,13-hexol 
• 131617-19-1 (3R,4S,5R,6S)-7-(benzyloxy)-3,5-(isopropylidenedioxy)-4,6-dimethylheptan-2-one 
• 131722-56-0 (2S,3R,4S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentanal 
• 131589-20-3 (2S,3R,4S,5R)-1-O-benzyl-3,5-O-isopropylidene-2,4,6-trimethyl-6-heptene-1,3,5-triol 
• 131589-43-0 (3R,4S,5R,6S)-7-Benzyloxy-2,4,6-trimethyl-hept-1-ene-3,5-diol 
• 220691-31-6 C₆₅H₉₄O₁₀Si₂ 
• 220691-97-4 C₅₈H₈₆O₁₀Si₂ 

Relevant academic research and scientific papers

Formal total synthesis of okadaic acid via regiocontrolled gold(I)-catalyzed spiroketalizations

Both C19 and C34 spiroketal domains of okadaic acid were assembled using gold(I) chloride catalyzed spiroketalizations, and the two resulting fragments were coupled to give the C15 - C38 fragment of okadaic acid, a known intermediate for the total synthesis of this important natural product.

Acyclic diastereoselective synthesis using tartrate ester modified crotylboronates. Double asymmetric reactions with α-methyl chiral aldehydes and synthesis of the C(19)-C(29) segment of rifamycin S

Double asymmetric reactions of the tartrate ester modified crotylboronates 1 and 2 and α-methyl chiral aldehydes are described. The reactions of the appropriate enantiomers of 1 and 2 with β-alkoxy-α-methylpropionaldehydes 11 provide adducts 12, 13, and 1

Chiral Synthesis via Organoboranes. 21. Allyl- and Crotylboration of α-Chiral Aldehydes with Diisopinocampheylboron as the Chiral Auxiliary

B-Allyldiisopinocampheylboranes have been screened for diastereofacial selectivity in their reaction with α-substituted chiral aldehydes.Both syn and anti products have been obtained in very high diastereoselectivities.Further, (E)-crotyldiisopinocampheylboranes and (Z)-crotyldiisopinocampheylboranes have been used for diastereofacial selectivity in their reaction with α-substituted chiral aldehydes.These crotylboranes, 20-23, are highly diastereoselective reagents and the corresponding (3,4- and 4,5-)-anti,syn, -anti,anti, and -syn,anti products have been obtained in very high facial selectivities; even the syn,syn product has been obtained in moderately good facial selectivity.Finally, the relative efficiences of the various chiral auxiliaries utilized in the literature for the allyl- and crotylboration have been compared with those achieved by the diisopinocampheylboron moiety.