916154-04-6

Basic information

• Product Name: ((2R,3R,4R)-4-((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)-3,4-dihydro-2H-pyran-2-yl)methanol
• Synonyms: ((2R,3R,4R)-4-((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)-3,4-dihydro-2H-pyran-2-yl)methanol
• CAS NO: 916154-04-6
• Molecular Weight: 380.557
• Mol File: 916154-04-6.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: ((2R,3R,4R)-4-((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)-3,4-dihydro-2H-pyran-2-yl)methanol(CAS DataBase Reference)
• NIST Chemistry Reference: ((2R,3R,4R)-4-((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)-3,4-dihydro-2H-pyran-2-yl)methanol(916154-04-6)
• EPA Substance Registry System: ((2R,3R,4R)-4-((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)-3,4-dihydro-2H-pyran-2-yl)methanol(916154-04-6)

Safety Data

• Hazardous Substances Data: 916154-04-6(Hazardous Substances Data)

Upstream product

• 111830-53-6 1,2-dideoxy-3,6-di-O-tert-butyldimethylsilyl-2-deoxy-D-arabino-1-hexenopyranose 
• 340320-92-5 tert-butyl(((2R,4aR,8R,8aR)-2-(4-methoxyphenyl)-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)dimethylsilane 
• 384346-91-2 3-O-tert-butyldimethylsilyl-4,6-O-(4-methoxybenzylidene)-D-(-)-glucal 
• 824-94-2 p-methoxybenzyl chloride 
• 913258-74-9 3,6-O-di-tert-butyldimethylsilyl-4-O-p-methoxybenzyl-D-glucal 

Downstream Products

• 1004999-96-5 C₂₁H₃₆O₆Si 
• 1440947-78-3 tert-butyl(((2S,3R,4R)-2-(iodomethyl)-6-methoxy-3-((4-methoxybenzyl)oxy)tetrahydro-2H-pyran-4-yl)oxy)dimethylsilane 
• 1440947-80-7 tert-butyl(((2S,3R,4R)-2-(iodomethyl)-6-methoxy-3-((4-methoxybenzyl)oxy)tetrahydro-2H-pyran-4-yl)oxy)dimethylsilane 

Relevant articles and documents

Synthesis of (-)-morphine: Application of sequential claisen/claisen rearrangement of an allylic vicinal diol

A detailed exploration of the synthesis of (-)-morphine based on sequential [3,3]-sigmatropic rearrangements is described. The sequential Claisen/Claisen rearrangements of an allylic vicinal diol resulted in the stereoselective formation of the two contiguous carbon centers, including a sterically encumbered quaternary carbon, in a single operation. The two ethyl esters generated in this reaction were successfully differentiated during a subsequent Friedel-Crafts-type cyclization. The (-)-morphine double bond was introduced at a late stage in our first-generation synthesis, but was formed at an earlier stage in the second-generation synthesis, resulting in a more efficient route to the end product.

METHOD OF FORMING OSELTAMIVIR AND DERIVATIVES THEREOF

A process is provided for the synthesis of 4,5-diamino cyclohexene carboxylate ester (1): or a pharmaceutically acceptable salt thereof. R1 - R3 are a silyl-, an aliphatic, alicyclic, aromatic, arylaliphatic, or an arylalicyclic group. R4, R11 and R12 are H, a silyl-group, an aliphatic, alicyclic, aromatic, arylaliphatic, or an arylalicyclic group. 3,4-Dihydropyran compound (9): with R5 and R6 being suitable protecting groups, is reacted to form aldehyde (4): which is oxidized and converted to N-substituted carbamate (3): with R7 being a suitable protecting group. (3) is, via oxazolinidone (13): converted to azido carboxylate ester (2): and then to 4,5-diamino cyclohexene carboxylate ester (1).

Formal synthesis of (-)-morphine from d-glucal based on the cascade Claisen rearrangement

The formal synthesis of (-)-morphine is described. The C-ring in morphine was prepared in an optically pure form from d-glucal using Ferrier's carbocyclization reaction, and the vicinal tertiary and quaternary stereocenters in the C-ring were stereoselect