19465-06-6

Upstream product

• 917-54-4 methyllithium 
• 2880-96-8 methyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside 
• 108-24-7 acetic anhydride 
• 95058-48-3 (1aR,2S,6R,7bR)-2-Methoxy-1a-methyl-6-phenyl-hexahydro-1,3,5,7-tetraoxa-cyclopropa[a]naphthalene 
• 3150-15-0 methyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside 
• 129588-82-5 C₁₂H₂₆AlOSi^(1-)*Li⁽¹⁺⁾ 
• 129588-81-4 C₈H₁₈AlSi^(1-)*Li⁽¹⁺⁾ 

Downstream Products

• 102368-16-1 2-Oxo-2H-pyridine-1-carbothioic acid O-((4aR,6S,7S,8S,8aS)-6-methoxy-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl) ester 
• 64526-80-3 methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-arabino-hexopyranoside 
• 56981-18-1 methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-3.O-<(thiomethyl)-thiocarbonyl>-α-D-altro-pyranoside 
• 82707-03-7 (2S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-5-methyl-3-methylene-tetrahydro-pyran-4-ol 
• 75879-81-1 Methyl 4,6-O-Benzylidene-2-deoxy-2-C-methyl-α-D-allopyranoside 
• 100-52-7 benzaldehyde 
• 64526-82-5 methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-3-O-methyl-α-D-allopyranoside 
• 82707-13-9 methyl 3-O-acetyl-4,6-O-benzylidene-2-C-methyl-α-D-allopyranoside 
• 82707-07-1 methyl 2,4-dideoxy-2-C-methyl-3-O-methyl-6-O-triphenylmethyl-α-D-xylo-hexopyranoside 
• 82707-17-3 methyl 4-chloro-2,4-dideoxy-2-C-methyl-3-O-methyl-6-O-triphenylmethyl-α-D-galactopyranoside 
• 82707-02-6 Acetic acid (2S,4S,5R,6S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-methoxy-5-methyl-3-methylene-tetrahydro-pyran-4-yl ester 
• 82731-51-9 methyl 3-O-acetyl-6-O-t-butyldiphenylsilyl-2-deoxy-C-methyl-α-D-allopyranoside 
• 82731-52-0 methyl 3-O-acetyl-6-O-t-butyldiphenylsilyl-2-deoxy-2-C-methyl-α-D-ribo-hexapyranoside-3-ulose 
• 92268-68-3 ((2S,3R,4R,5R,6S)-4-Benzyloxy-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-{2-[(1R,2S)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-1-methyl-propyl]-[1,3]dithian-2-yl}-methanone 

Relevant academic research and scientific papers

Introduction of a chiral centre on C-6 of a carbohydrate unit: Application to the synthesis of the C-2 to C-15 fragment of ionomycin

Glucose is converted into the α,β-unsaturated urono-8,4-lactone 29 using an intramolecular Wadsworth-Emmons reaction. Higher order cuprates add to the lactone to provide the C-6 substituted carbohydrate derivative with high stereoselectivity. This product can be converted into the dithiane 34b which when coupled with an appropriate epoxide yields compound 37 which contains the C-2 to C-15 fragment of ionomycin with the correct absolute stereochemistry at each asymmetric centre for conversion into ionomycin.

Oxirane Ring Opening of Anhydrosugars with Alkynyl- and Alkenylaluminates

The oxirane ring opening of 2,3-anhydro-pentopyranosides and 2,3-anhydro-hexopyranosides with organoaluminate reagents is described.By the use of trialkylalkynylaluminates, deoxy-alkynyl sugars are obtained in good yields.Trialkylalkenylaluminates are les

An Approach to the Total Synthesis of the Prelog-Djerassi Lactone

An approach to the synthesis of the Prelog-Djerassi lactone using D-glucose as a starting material is described.The use of Swern oxidation provides an efficient means of preparing carbohydrate ketones.An unusual departure from the normal reaction pathway