64551-84-4

Upstream product

• 3427-20-1 methyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside 
• 2873-29-2 D-glucal triacetate 
• 3427-20-1 methyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranoside 

Downstream Products

• 162189-43-7 (1S,6S,7R)-6,7-Dimethoxy-1-phenyl-8-trityloxy-octan-1-ol 
• 162189-45-9 (2R,3S,8S)-8-(tert-butyldimethylsilyloxy)-2,3-dimethoxy-8-phenyloctan-1-ol 
• 122547-72-2 (1S,2S,3E,5R,6S,11S,14S,15R,16R,17S,18S)-15,17-dihydroxy-5,6,16-trimethoxy-2,14,18-trimethyl-11-phenyl-12,19-dioxabicyclo[13.3.1]nonadec-3-en-13-one 
• 162189-40-4 2-((3S,4R)-3,4-Dimethoxy-5-trityloxy-pentyl)-[1,3]dithiane 

Relevant academic research and scientific papers

Synthesis of paclitaxel. 1. synthesis of the abc ring of paclitaxel by SmI2-mediated cyclization

A convergent synthesis of the ABC ring of antitumor natural product paclitaxel (Taxol) is described. SmI2-mediated reductive cyclization of an allylic benzoate possessing an aldehyde function, synthesized from tri-O-acetyl-d-glucal and 1,3-cyclohexanedione, smoothly afforded the highly strained 6-8-6 tricarbocyclic structure in 66% yield.

Traceless chiral auxiliaries for the allene ether Nazarov cyclization

(Chemical Equation Presented) The key stereochemical factors that determine transfer of asymmetry from the chiral auxiliary to the cyclopentenone in the allene ether version of the Nazarov reaction have been elucidated. On the basis of the new insights in

Design of chiral auxiliaries for the allene ether Nazarov cyclization

A 1,3- or a 1,4-cis axial tert-butyldimethylsilyloxy substituent on the pyranose derived chiral auxiliary for the allene ether Nazarov cyclization leads to products in high optical purity. α-Pyranose and β-pyranose derived auxiliaries lead to enantiomeric products. Copyright

Diastereoselective synthesis of 2′,3′-dideoxy- β-C- glucopyranosides as intermediates for the synthesis of 2′,3′- dideoxy-β-D-glucopyranosyl-C-nucleosides

An extension of the Vorbrueggen method of nucleotide synthesis for the synthesis of C-glucopyranosides, as intermediates for C-nucleosides, is described. It could be shown that the diastereoselectivity of the reaction can be tuned by a simple change of protecting groups. Copyright Taylor & Francis Group, LLC.

Synthesis of C7-C16-alkyl 2,3-dideoxy glucosides from glucose and fatty alcohols

C7-C16-alkyl 2,3-dideoxy glucosides have been synthesized from glucose and C7-C16-alkanols by Ferrier reaction using boron trifluoride etherate (BF3·Et2O) as Lewis acid catalyst in key step.

Simple Designs for the Construction of Complex Trans-Fused Polyether Toxin Frameworks. A Linear Strategy Based on Entropically Favored Oxirane Ring Enlargement in Epoxycycloalkenes Followed by Carbon-Carbon or Carbon-Oxygen Bond-Forming Cyclizations

A successful design for the construction of trans-fused medium-size cyclic ethers is described.The key features of the synthesis are as follows: (i) intramolecular oxirane ring expansion in cycloalkenes to give bridged oxabicyclic systems and (ii) linear, one- or two-directional synthetic operations which generate external oxocycles in single reaction steps.The general approach involves the intramolecular addition of a stable γ-alkoxy-substituted allylstannane to an aldehyde carbonyl group, and the entire reaction is conducted in a one-pot process which includes the following: (i) vic-diol fragmentation from the bridged oxabicyclic precursor and (ii) Lewis acid-induced cyclization of the resulting aldehyde-allylic tin system.While the present strategy was mostly developed around racemic models, the potential for adoption of enantioselective features is immediate.The versatility, scope, limitations, and potential applications of the present technology are discussed in detail.

SYNTHESIS AND STEREOCHEMICAL CHARACTERIZATION OF OPTICALLY ACTIVE 2-METHOXY-3,4-DIHYDRO-2H-PYRAN

Samples of (+)-2-methoxy-3,4-dihydro-2H-pyran (1) have been prepared starting from methyl α-D-glucopyranoside and from tri-O-acetyl-D-glucal; the absolute configuration as well as the maximum rotatory power of 1 have been established.