321921-91-9

Upstream product

• 251319-55-8 (R)-4-Benzyl-3-((E)-(2R,3S)-6-benzyloxy-3-hydroxy-2-methyl-hex-4-enoyl)-oxazolidin-2-one 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 100-39-0 benzyl bromide 
• 81028-03-7 (Z)-4-benzyloxy-but-2-en-1-ol 
• 122751-47-7 (Z)-4-phenylmethoxy-but-2-en-1-al 
• 69152-87-0 4-benzyloxycrotonaldehyde 
• 251319-65-0 (2Z,6E)-(4S,5S)-8-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-octa-2,6-dienoic acid methyl ester 
• 88738-78-7 bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate 
• 251319-56-9 (2R,3R,4E)-2-methyl-3-(tert-butyldimethylsilyloxy)-6-(phenylmethoxy)hex-4-en-1-al 
• 321921-83-9 (E)-(2R,3S)-6-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-hex-4-enoic acid methoxy-methyl-amide 

Downstream Products

• 251319-59-2 (2R,3R,4R,5R,6Z)-3-benzoyloxy-5-methyl-4,8-di-(tert-butyldimethylsiloxy)-2,3-(oxirane) oct-6-en-1,2-diol 
• 251319-66-1 (2Z,4R,5R,6R,7R)-6-benzoyloxy-4-methyl-1,5-di-(tert-butyldimethylsiloxy)-7,8-di-(triethylsiloxy)oct-2-ene 
• 251319-60-5 (2R,3S,4R,5R,6R,7R)-6-benzoyloxy-4-methyl-1,5-di-(tert-butyldimethylsiloxy)-7,8-di-(triethylsilyloxy)octa-2,3-oxirane 
• 321921-85-1 (2Z,4R,5R,6R)-6-benzoyloxy-4-methyl-1,5-di-(tert-butyldimethylsiloxy)-7,8-(isopropylidenedioxy)oct-2-ene 
• 251319-68-3 (2R,4aR,6R,7S,8R,8aR)-6-[(R)-1-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-8-(tert-butyl-dimethyl-silanyloxy)-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 
• 321921-84-0 Benzoic acid (1R,2R,3S)-2-(tert-butyl-dimethyl-silanyloxy)-3-[(2S,3R)-3-(tert-butyl-dimethyl-silanyloxymethyl)-oxiranyl]-1-((R)-1,2-dihydroxy-ethyl)-butyl ester 
• 251319-61-6 (2R,3S,4R,5R,6R)-2-{[1'R]-2-(tert-butyldimethylsiloxy)-1'-hydroxyethyl}-3-methyl-4-(tert-butyldimethylsilyloxy)-5-benzyloxy-6-hydroxymethyl-1-tetrahydropyran 
• 251319-67-2 (R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-[(2R,4aR,6R,7S,8R,8aR)-8-(tert-butyl-dimethyl-silanyloxy)-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethanol 
• 251319-63-8 (R)-2-Benzyloxy-2-[(2R,4aR,6R,7S,8R,8aR)-8-(tert-butyl-dimethyl-silanyloxy)-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethanol 
• 321921-94-2 (2Z,4R,5R,6R,7R)-6-benzoyloxy-4-methyl-1,5-di-(tert-butyldimethylsiloxy)-7,8-di-(triphenylsiloxy)oct-2-ene 
• 321921-93-1 (2Z,4R,5R,6R,7R)-6-benzoyloxy-4-methyl-1,5-di-(tert-butyldimethylsiloxy)-7,8-di-(ttrimethylsiloxy)oct-2-ene 
• 321921-92-0 [(2E,6Z)-(4S,5S)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5-methyl-octa-2,6-dienyloxymethyl]-benzene 

Relevant academic research and scientific papers

Asymmetric epoxide cyclisation route to the F-pyran fragment of the altohyrtins and key aldol studies

The evolution of an asymmetric synthesis of a differentially protected F-pyran ring of the altohyrtins is described, which relies on a key intramolecular cyclisation of a C43 hydroxyl group onto a C38-C39 epoxide. The C38-C39 epoxide stereochemistry was achieved through optimisation of substrate control. Key aldol studies towards coupling the F-pyran ring with an E-pyran ring precursor was investigated, but unsuccessful. (C) 2000 Elsevier Science Ltd.

Asymmetric synthesis of the F-pyran fragment of the altohyrtins

The asymmetric synthesis of a differentially protected F-pyran ring of the altohyrtins has been achieved through an intramolecular cyclisation of a C43 hydroxyl group onto a C38-C39 epoxide. Absolute stereochemistry was derived from an Evans boron aldol to control C40 and C41, the C42-C43 hydroxyl stereocentres from a Sharpless(-)-diethyl tartrate controlled epoxidation and the remaining stereocentres from substrate controlled diastereoselection.