1,5-anhydro-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-1-phenylsulfonyl-D-arabino-hex-1-enitol

Base Information

Chemical Name:1,5-anhydro-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-1-phenylsulfonyl-D-arabino-hex-1-enitol
CAS No.:142393-19-9
Molecular Formula:C₂₅H₃₂O₆SSi
Molecular Weight:488.677
Hs Code.:

Synonyms:1,5-anhydro-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-1-phenylsulfonyl-D-arabino-hex-1-enitol

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Chemical Property of 1,5-anhydro-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-1-phenylsulfonyl-D-arabino-hex-1-enitol

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Technology Process of 1,5-anhydro-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-1-phenylsulfonyl-D-arabino-hex-1-enitol

There total 10 articles about 1,5-anhydro-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-1-phenylsulfonyl-D-arabino-hex-1-enitol 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: 88.0%

: 331456-80-5
2,3-Di-O-(tert-butyldimethylsilyl)-4,6-O-benzylidene-β-D-xylopyranosyl phenyl sulfone

: 142393-19-9,131389-38-3
1,5-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-2-deoxy-1-phenylsulfonyl-D-arabino-hex-1-enitol

Guidance literature:: With methyllithium lithium bromide; In tetrahydrofuran; at -78 ℃; for 0.333333h;
DOI:10.1055/s-2001-10802

Reference yield: 80.0%

: 142270-08-4
4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-O-methyl-β-D-glucopyranosyl phenyl sulfone

: 142393-19-9
1,5-anhydro-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-1-phenylsulfonyl-D-arabino-hex-1-enitol

Guidance literature:: With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.333333h;
DOI:10.1016/S0008-6215(00)90552-4

Reference yield:

: phenyl 3-O-(tert-butyldimethysilyl)-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside

: 142393-19-9,131389-38-3
1,5-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-2-deoxy-1-phenylsulfonyl-D-arabino-hex-1-enitol

Guidance literature:: Multi-step reaction with 3 steps

1: 72 percent / DIPEA / CH₂Cl₂ / 12 h / 20 °C

2: 83 percent / MCPBA; NaHCO₃ / CH₂Cl₂ / 12 h / 0 - 20 °C

3: 88 percent / MeLi*LiBr / tetrahydrofuran / 0.33 h / -78 °C

With methyllithium lithium bromide; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1055/s-2001-10802