109958-35-2

Upstream product

• 68907-47-1 methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-altro-pyranoside 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 19465-06-6 methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-altropyranoside 
• 2880-96-8 methyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside 

Downstream Products

• 147910-19-8 (R)-2-((2S,3S,4S,5S)-3-Benzyloxy-5-methoxy-4-methyl-tetrahydro-furan-2-yl)-2-methoxymethoxy-ethanol 
• 147910-18-7 [(R)-2-((2S,3S,4S,5S)-3-Benzyloxy-5-methoxy-4-methyl-tetrahydro-furan-2-yl)-2-methoxymethoxy-ethoxy]-tert-butyl-dimethyl-silane 
• 147910-24-5 (E)-(1S,2R)-1-((2S,3S,4S,5S)-3-Benzyloxy-5-methoxy-4-methyl-tetrahydro-furan-2-yl)-1-methoxymethoxy-2-methyl-pent-3-en-2-ol 
• 147910-22-3 (E)-(1S,2S)-1-((2S,3S,4S,5S)-3-Benzyloxy-5-methoxy-4-methyl-tetrahydro-furan-2-yl)-1-methoxymethoxy-2-methyl-pent-3-en-2-ol 
• 147910-26-7 (E)-(1R,2S,5R)-5-((2S,3S,4S,5S)-3-Benzyloxy-5-methoxy-4-methyl-tetrahydro-furan-2-yl)-1-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-5-methoxymethoxy-2,4-dimethyl-pent-3-en-1-ol 
• 109914-89-8 methyl 3-O-benzyl-2-deoxy-2-C-methyl-β-D-altropyranoside 
• 75837-45-5 methyl 3-O-benzyl-2-deoxy-2-C-methyl-α-D-altropyranoside 
• 109914-97-8 methyl 3-O-benzyl-2-deoxy-6-O-(diphenyl-t-butylsilyl)-2-C-methyl-4-C-(trimethylsilylmethyl)-α-D-idopyranoside 
• 109914-98-9 methyl 3-O-benzyl-2-deoxy-6-O-(diphenyl-t-butylsilyl)-2-C-methyl-4-C-(trimethylsilylmethyl)-α-D-altro-pyranoside 
• 109914-90-1 methyl 3-O-benzyl-2-deoxy-6-O-(diphenyl-t-butylsilyl)-2-C-methyl-α-D-altropyranoside 

Relevant academic research and scientific papers

Synthetic Studies toward Ciguatoxin. Stereocontrolled Construction of the KLM Ring Fragment

The first stereoselective synthesis of the KLM ring fragment of ciguatoxin is reported including as a key step 7-endo selective cyclization of epoxy alcohol to construct a fully substituted oxepane ring (12 -> 13).

Stereocontrolled synthesis of the JKLM ring fragment of ciguatoxin

A highly stereocontrolled synthesis of the JKLM ring fragment of ciguatoxin has been achieved. The present synthesis starts with methyl 4,6-O- benzylidene-2-deoxy-2-C-methyl-α-D-altropyranoside, whose configurations and substituents at C2-C5 correspond to those at C46-C49 of ciguatoxin, and involves as the key step base-induced 7-endo selective cyclization of a hydroxy epoxide for the efficient construction of the fully substituted oxepane ring K. Construction of the spiroether ring M was achieved by introduction of an allyl group to the ring L lactone followed by asymmetric dihydroxylation to install the C54 stereogenic center and acid-induced spiroketalization to furnish the protected KLM ring system. Finally, ring J was constructed by the method of Nicolaou to complete the synthesis of the JKLM ring fragment. The synthesis of a carboxylic acid derivative and its conjugation to carrier proteins to give an artificial antigen for development of an immunoassay system for the parent toxin molecule are also reported.

Diastereoselective [2,3] Wittig rearrangement of carbohydrate-derived tertiary allylic ethers. 2. Synthesis of an advanced rapamycin intermediate fromD-glucose

The advanced rapamycin intermediate 26 has been prepared by an iterative sigmatropic sequence incorporating the diastereoselective [2,3] Wittig rearrangement of a D-glucofuranose-derived tertiary allylic ether.

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