1004999-96-5

Basic information

• Product Name: C₂₁H₃₆O₆Si
• CAS NO: 1004999-96-5
• Molecular Weight: 412.599
• Mol File: 1004999-96-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: C₂₁H₃₆O₆Si(CAS DataBase Reference)
• NIST Chemistry Reference: C₂₁H₃₆O₆Si(1004999-96-5)
• EPA Substance Registry System: C₂₁H₃₆O₆Si(1004999-96-5)

Safety Data

• Hazardous Substances Data: 1004999-96-5(Hazardous Substances Data)

Upstream product

• 916154-04-6 ((2R,3R,4R)-4-((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)-3,4-dihydro-2H-pyran-2-yl)methanol 
• 67-56-1 methanol 

Downstream Products

• 1004999-97-6 tert-butyl(((2S,3R,4R)-2-(iodomethyl)-6-methoxy-3-((4-methoxybenzyl)oxy)tetrahydro-2H-pyran-4-yl)oxy)dimethylsilane 
• 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

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

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.