4,6-O-benzylidene-2,3-bis-O-(tert-butyldimethylsilyl)-D-glucono-1,5-lactone

Base Information

Chemical Name:4,6-O-benzylidene-2,3-bis-O-(tert-butyldimethylsilyl)-D-glucono-1,5-lactone
CAS No.:498554-04-4
Molecular Formula:C₂₅H₄₂O₆Si₂
Molecular Weight:494.776
Hs Code.:

Synonyms:4,6-O-benzylidene-2,3-bis-O-(tert-butyldimethylsilyl)-D-glucono-1,5-lactone

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Chemical Property of 4,6-O-benzylidene-2,3-bis-O-(tert-butyldimethylsilyl)-D-glucono-1,5-lactone

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Technology Process of 4,6-O-benzylidene-2,3-bis-O-(tert-butyldimethylsilyl)-D-glucono-1,5-lactone

There total 1 articles about 4,6-O-benzylidene-2,3-bis-O-(tert-butyldimethylsilyl)-D-glucono-1,5-lactone 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: 92.0%

: 113533-88-3,113533-89-4
4,6-O-benzylidene-2,3-bis-O-(tert-butyldimethylsilyl)-D-glucopyranose

: 498554-04-4
4,6-O-benzylidene-2,3-bis-O-(tert-butyldimethylsilyl)-D-glucono-1,5-lactone

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 0 ℃;
DOI:10.1016/S0040-4020(02)01329-7

Reference yield: 100.0%

: 75-24-1
trimethylaluminum

: 498554-04-4
4,6-O-benzylidene-2,3-bis-O-(tert-butyldimethylsilyl)-D-glucono-1,5-lactone

: 498554-05-5
(1R,3R,6R,9R,10S)-9,10-bis(tert-butyldimethylsilyloxy)-8-methylene-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decane

Guidance literature:: trimethylaluminum; With titanocene dichloride; In toluene; at 23 ℃; for 72h;

4,6-O-benzylidene-2,3-bis-O-(tert-butyldimethylsilyl)-D-glucono-1,5-lactone; In tetrahydrofuran; toluene; at 0 - 24 ℃;
DOI:10.1016/S0040-4020(02)01329-7

Reference yield:

: 498554-04-4
4,6-O-benzylidene-2,3-bis-O-(tert-butyldimethylsilyl)-D-glucono-1,5-lactone

: {(1R,3R,6R,9S,10S)-9,10-bis(tert-butyldimethylsilyloxy)-3-phenyl-2,4,7-trioxabicyclo[4.4.0]dec-8-yl}methanol

Guidance literature:: Multi-step reaction with 2 steps

1.1: titanocene dichloride / toluene / 72 h / 23 °C

1.2: 100 percent / toluene; tetrahydrofuran / 0 - 24 °C

2.1: BH₃*THF / tetrahydrofuran / 4.5 h / 0 °C

2.2: 80 percent / aq. NaOH; H₂O₂ / tetrahydrofuran / 1.5 h / 24 °C

With borane-THF; titanocene dichloride; In tetrahydrofuran; toluene; 1.2: Tebbe olefination;
DOI:10.1016/S0040-4020(02)01329-7