232603-08-6

Upstream product

• 40653-15-4 methyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside 
• 34212-64-1 methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 

Downstream Products

• 181265-87-2 3-((2R,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propan-1-ol 
• 232603-11-1 methyl-2,3,4-tri-O-benzyl-α-D-mannopyranosidocturonic acid 
• 181488-54-0 (2R,3R,4S,4aS,8aS)-3,4-Bis-benzyloxy-2-[(E)-3-((2S,3S,4aS,8aR)-3-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-allyl]-octahydro-pyrano[3,2-b]pyran 
• 181262-47-5 (2R,3R,4S,4aS,8aS)-3,4-Bis-benzyloxy-2-[(Z)-3-((2S,3S,4aS,8aR)-3-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-allyl]-octahydro-pyrano[3,2-b]pyran 
• 181262-86-2 (2R,3R,4R,4aS,8aS)-2-[(2R,3S)-2,3-Bis-benzyloxy-3-((2R,3S,4aS,8aR)-3-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propyl]-4-(4-methoxy-benzyloxy)-octahydro-pyrano[3,2-b]pyran-3-ol 
• 181488-53-9 (1R,2R)-1-((2S,3S,4aS,8aR)-3-Benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-3-((2R,3R,4S,4aS,8aS)-3,4-bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propane-1,2-diol 
• 181488-55-1 (1S,2R)-1-((2S,3S,4aS,8aR)-3-Benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-3-((2R,3R,4S,4aS,8aS)-3,4-bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propane-1,2-diol 
• 181488-56-2 (1R,2S)-1-((2S,3S,4aS,8aR)-3-Benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-3-((2R,3R,4S,4aS,8aS)-3,4-bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propane-1,2-diol 
• 181262-50-0 (1S,2S)-1-((2S,3S,4aS,8aR)-3-Benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-3-((2R,3R,4S,4aS,8aS)-3,4-bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propane-1,2-diol 
• 181266-76-2 Acetic acid (1S,2R)-2-acetoxy-1-((2R,3S,4aS,8aR)-3-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-3-((2R,3R,4S,4aS,8aS)-3,4-bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propyl ester 
• 181262-44-2 (2R,3R,4S,4aS,8aS)-3,4-Bis-benzyloxy-2-[3-((2S,3S,4aS,8aR)-3-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-prop-2-ynyl]-octahydro-pyrano[3,2-b]pyran 
• 181265-92-9 Methanesulfonic acid 3-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propyl ester 
• 181266-17-1 (2S,3S,4S,4aR,8aR)-3-Benzyloxy-2-methoxy-4-(4-methoxy-benzyloxy)-octahydro-pyrano[3,2-b]pyran 
• 181266-10-4 (2S,3S,4S,4aS,8aR)-2-Methoxy-3-(4-methoxy-benzyloxy)-octahydro-pyrano[3,2-b]pyran-4-ol 

Relevant academic research and scientific papers

An olefin metathesis route for the preparation of (1 → 6)-linked C-disaccharide glycals. A convergent and flexible approach to C-saccharide synthesis

A convergent route to a variety of C-1-disaccharide glycals based on the olefin metathesis reaction of enol ethers and alkenes is described. The DCC-mediated coupling reaction of a variety of pentose enitols (1a-c) with a number of C-5- and C-6-monosaccharide carboxylic acids (2a-e) gave the corresponding esters 3a-1 in good yield. Methylenation of these compounds was followed by ring-closing metathesis, mediated by the Schrock molybdenum catalyst 8 in warm toluene, to provide the target C-disaccharide glycals 5a-1. The formed enol ether double bond in 5a was then transformed, via standard manipulations, into a variety of C-disaccharide derivatives 21-25.

Convergent preparation of 1,6-linked C-disaccharides via olefin metathesis

The DCC mediated coupling reaction of 3,4,6-tri-O-benzyl-1,2-dideoxy-D- arabino-hex-1-enitol (5a) with a variety of sugar based carboxylic acids 6a- d gave esters 7a-d in good yield. Methylenation of the formed esters led to the acyclic enol ethers 8a-d a

Complete relative stereochemistry of maitotoxin

By addressing the relative stereochemistry of the four acyclic portions via organic synthesis, the complete relative stereochemistry of maitotoxin (MTX) has been established as 1B. The relative stereochemistry of the C.1-C.15 portion was elucidated via a two-phase approach: (1) the synthesis of the eight diastereomers possible for model C, representing the C.1-C.11 portion, and the eight diastereomers possible for model D, representing the C.11-C.15 portion, and the comparison of their proton and carbon NMR characteristics with those of MTX, concluding that 9 and 35 represent the relative stereochemistry of the corresponding portions of MTX; (2) the synthesis of the two remote diastereomers 51 and 52, and comparison of their proton and carbon NMR characteristics with those of MTX, concluding that 51 represents the relative stereochemistry of the C.1-C.15 portion of MTX. The relative stereochemistry of the C.35-C.39, C.63-C.68, and C.134-C.142 acyclic portions was established via (1) the synthesis of the 8, 8, and 16 diastereomers possible for models E, F, and G, respectively, and (2) the comparison of their proton and carbon NMR characteristics with those of MTX, concluding that 81, 117, and 187, respectively, represent the relative stereochemistry of the corresponding portions of MTX. Some biogenetic considerations have been given to speculate on the absolute configuration of MTX. The vicinal proton coupling constants observed for models 51, 81, 117, and 187 were used to elucidate their preferred solution conformation. Assembling the preferred solution conformations found for the four acyclic portions allows one to suggest that the approximate global conformation of MTX is represented by the shape of a hook, with the C.35-C.39 portion being its curvature. MTX appears to be conformationally relatively rigid, except for conformational flexibility around the C.7-C.9 and C.12-C.14 portions. On the basis of the experimental results gained in the current work, coupled with those in the AAL-toxin/fumonisin area, it has been pointed out that the structural properties of 51, 81, 117, 187 and their diastereomers are inherent to the specific stereochemical arrangement of the small substituents on the carbon backbone and are independent from the rest of the molecule. Thus, it has been suggested that each of these diastereomers has the capacity to install a unique structural characteristic through a specific stereochemical arrangement of substituents on the carbon backbone, and that fatty acids and related classes of compounds may be able to carry specific information and serve as functional materials in addition to structural materials.