87318-99-8

Upstream product

• 2999-74-8 dimethylmagnesium 
• 220094-49-5 tert-Butyl-((1S,2R,4S,5R,6S)-4-methoxy-5-methyl-3,7-dioxa-bicyclo[4.1.0]hept-2-ylmethoxy)-diphenyl-silane 
• 220094-48-4 Dimethyl-carbamic acid (2R,3R,4S,5R,6S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-3-chloro-6-methoxy-5-methyl-tetrahydro-pyran-4-yl ester 
• 194149-26-3 methyl 2,3:4,6-di-O-benzylidene-α-D-mannopyranoside 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 220094-47-3 (2R,3S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-5-methyl-tetrahydro-pyran-3,4-diol 
• 68907-47-1 methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-altro-pyranoside 
• 121467-58-1 (2R,4aR,6S,7S,8aR)-6-Methoxy-7-methyl-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one 
• 101978-79-4 Methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-allopyranoside 
• 75-16-1 methylmagnesium bromide 

Downstream Products

• 162189-48-2 [(S)-3-((2S,3R,4R,5R,6S)-4-Benzyloxy-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-3-methoxy-prop-1-ynyl]-tert-butyl-dimethyl-silane 
• 82707-04-8 methyl 3-O-benzyl-6-O-t-butyldiphenylsilyl 2,4-dideoxy-2,4-di-C-methyl-α-D-gulopyranoside 

Relevant academic research and scientific papers

Synthesis of epothilones B and D from D-glucose

An enantiospecific total synthesis of epothilones B and D from D-glucose is reported.

Total synthesis of soraphen A(1α)

The convergent synthesis of macrolide soraphen A(1α) is described starting from glucose (western part) and mannose (eastern part). Mannose was converted into a 2-deoxyribohexopyranoside that could be methylated and reduced stereoselectively. Chain elongation at C-6 was carried out by stereoselective addition of a magnesium acctylide. The two fragments (western and eastern) were assembled by a Julia olefination followed by macrolactonization. The introduction of the methyl group at C-2 of norsoraphen occurred stereoselectively for thermodynamic reasons.