858676-45-6

Basic information

• Product Name: (+)-methyl (2S,3S,4S,6R)-[6-(2-benzyloxyethyl)-4-hydroxy-3-methyltetrahydropyran-2-yl]-acetate
• Synonyms: (+)-methyl (2S,3S,4S,6R)-[6-(2-benzyloxyethyl)-4-hydroxy-3-methyltetrahydropyran-2-yl]-acetate
• CAS NO: 858676-45-6
• Molecular Weight: 322.401
• Mol File: 858676-45-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (+)-methyl (2S,3S,4S,6R)-[6-(2-benzyloxyethyl)-4-hydroxy-3-methyltetrahydropyran-2-yl]-acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-methyl (2S,3S,4S,6R)-[6-(2-benzyloxyethyl)-4-hydroxy-3-methyltetrahydropyran-2-yl]-acetate(858676-45-6)
• EPA Substance Registry System: (+)-methyl (2S,3S,4S,6R)-[6-(2-benzyloxyethyl)-4-hydroxy-3-methyltetrahydropyran-2-yl]-acetate(858676-45-6)

Safety Data

• Hazardous Substances Data: 858676-45-6(Hazardous Substances Data)

Upstream product

• 1256553-74-8 methyl (4S,5S,7R,E)-(-)-9-(benzyloxy)-5,7-dihydroxy-4-methylnon-2-enoate 
• 67-56-1 methanol 
• 870095-89-9 (+)-methyl (2E,5S,7E)-5-(2-benzyloxyethyl)-4-oxa-nona-2,7-dienoate 
• 858676-46-7 [(2S,3R,4S,6R)-6-(2-Benzyloxy-ethyl)-4-hydroxy-3-methyl-tetrahydro-pyran-2-yl]-acetic acid 
• 186581-53-3 diazomethane 

Downstream Products

• 1020267-36-0 C₂₆H₄₀O₉ 
• 1020267-37-1 C₂₆H₄₀O₉ 
• 858676-47-8 (+)-methyl (2S,3S,4S,6R)-[6-(2-benzyloxyethyl)-3-methyl-(4-triisopropylsilanyloxy)-tetrahydropyran-2-yl]-acetate 

Relevant articles and documents

Tetrahydropyran synthesis by intramolecular conjugate addition to enones: Synthesis of the clavosolide tetrahydropyran ring

The synthesis of a tetrahydropyran intermediate for clavosolide A is reported, employing a combination of cross-metathesis and intramolecular oxa-Michael addition. The intramolecular oxa-Michael addition to ,-unsaturated esters requires the use of strong bases and can result in either modest yields or stereoisomeric mixtures, and can be highly variable according to the substrate structure. In contrast, the corresponding ketones cyclise under very mild conditions to give the 2,6-cis-isomers directly. The use of appropriately substituted ketones allows efficient conversion into esters.

Total synthesis of the marine natural product (-)-clavosolide A

The total synthesis of the marine metabolite clavosolide A is reported which confirms the structure and absolute configuration of the natural product as the symmetrical diolide glycosylated by permethylated D-xylose moieties, 2.

Stereoselective synthesis of the tetrahydropyran core of polycarvernoside A

(Chemical Equation Presented) A concise and stereoselective synthesis of the tetrasubstituted tetrahydropyran core of polycavernoside A was achieved in 55% overall yield from 3-benzyloxypropanal. A stereoselective allyl transfer reaction was used in the synthesis of enol ether 18 followed by a TFA-mediated cyclization to create the three new asymmetric centers in the tetrahydropyran with complete stereocontrol in a single-pot process.