(4'R)-1,2-O-isopropylidene-3-O-[3'-(1-methylethylidene)-4'-trimethylsilylazetidin-2'-on-4'-yl]-5-O-trityl-α-D-xylofuranose

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Chemical Name:(4'R)-1,2-O-isopropylidene-3-O-[3'-(1-methylethylidene)-4'-trimethylsilylazetidin-2'-on-4'-yl]-5-O-trityl-α-D-xylofuranose
CAS No.:308279-20-1
Molecular Formula:C₃₆H₄₃NO₆Si
Molecular Weight:613.826
Hs Code.:

Synonyms:(4'R)-1,2-O-isopropylidene-3-O-[3'-(1-methylethylidene)-4'-trimethylsilylazetidin-2'-on-4'-yl]-5-O-trityl-α-D-xylofuranose

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Chemical Property of (4'R)-1,2-O-isopropylidene-3-O-[3'-(1-methylethylidene)-4'-trimethylsilylazetidin-2'-on-4'-yl]-5-O-trityl-α-D-xylofuranose

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Technology Process of (4'R)-1,2-O-isopropylidene-3-O-[3'-(1-methylethylidene)-4'-trimethylsilylazetidin-2'-on-4'-yl]-5-O-trityl-α-D-xylofuranose

There total 2 articles about (4'R)-1,2-O-isopropylidene-3-O-[3'-(1-methylethylidene)-4'-trimethylsilylazetidin-2'-on-4'-yl]-5-O-trityl-α-D-xylofuranose which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 62.0%

: 1189-71-5
isocyanate de chlorosulfonyle

: 308279-18-7
1,2-O-isopropylidene-3-O-(3'-methyl-1'-trimethylsilylbuta-1',2'-dienyl)-5-O-trityl-α-D-xylo-furanose

: (4'S)-1,2-O-isopropylidene-3-O-[3'-(1-methylethylidene)-4'-trimethylsilylazetidin-2'-on-4'-yl]-5-O-trityl-α-D-xylofuranose

: 308279-20-1
(4'R)-1,2-O-isopropylidene-3-O-[3'-(1-methylethylidene)-4'-trimethylsilylazetidin-2'-on-4'-yl]-5-O-trityl-α-D-xylofuranose

Guidance literature:: isocyanate de chlorosulfonyle; 1,2-O-isopropylidene-3-O-(3'-methyl-1'-trimethylsilylbuta-1',2'-dienyl)-5-O-trityl-α-D-xylo-furanose; With sodium carbonate; In toluene; at -70 - -30 ℃; for 1.5h;

With sodium bis(2-methoxyethoxy)aluminium dihydride; In toluene; at -70 ℃; for 30h; Title compound not separated from byproducts;
DOI:10.1016/S0957-4166(00)00260-3

Reference yield:

: 262300-84-5
1,2-O-isopropylidene-3-O-(3'-methylbuta-1',2'-dienyl)-5-O-trityl-α-D-xylofuranose

: 308279-20-1
(4'R)-1,2-O-isopropylidene-3-O-[3'-(1-methylethylidene)-4'-trimethylsilylazetidin-2'-on-4'-yl]-5-O-trityl-α-D-xylofuranose

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / -30 °C

1.2: 87 percent / hexane; tetrahydrofuran / 0.75 h / -30 - 20 °C

2.1: Na₂CO₃ / toluene / 1.5 h / -70 - -30 °C

2.2: 62 percent / Red-Al / toluene / 30 h / -70 °C

With n-butyllithium; sodium carbonate; In tetrahydrofuran; hexane; toluene; 1.1: Metallation / 1.2: sililation / 2.1: Cycloaddition / 2.2: reductive cleavage;
DOI:10.1016/S0957-4166(00)00260-3