3-C-(2-benzyloxyethyl)-6-O-(tert-butyldimethylsilyl)-3,5-dideoxy-1,2-O-isopropylidene-5-C-toluenesulfonyloxymethyl-β-L-talofuranose

Base Information

Chemical Name:3-C-(2-benzyloxyethyl)-6-O-(tert-butyldimethylsilyl)-3,5-dideoxy-1,2-O-isopropylidene-5-C-toluenesulfonyloxymethyl-β-L-talofuranose
CAS No.:113918-92-6
Molecular Formula:C₃₂H₄₈O₈SSi
Molecular Weight:620.88
Hs Code.:

Synonyms:3-C-(2-benzyloxyethyl)-6-O-(tert-butyldimethylsilyl)-3,5-dideoxy-1,2-O-isopropylidene-5-C-toluenesulfonyloxymethyl-β-L-talofuranose

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Chemical Property of 3-C-(2-benzyloxyethyl)-6-O-(tert-butyldimethylsilyl)-3,5-dideoxy-1,2-O-isopropylidene-5-C-toluenesulfonyloxymethyl-β-L-talofuranose

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Technology Process of 3-C-(2-benzyloxyethyl)-6-O-(tert-butyldimethylsilyl)-3,5-dideoxy-1,2-O-isopropylidene-5-C-toluenesulfonyloxymethyl-β-L-talofuranose

There total 8 articles about 3-C-(2-benzyloxyethyl)-6-O-(tert-butyldimethylsilyl)-3,5-dideoxy-1,2-O-isopropylidene-5-C-toluenesulfonyloxymethyl-β-L-talofuranose 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: 95.0%

: 113918-93-7
3-C-(2-benzyloxyethyl)-5-C-(tert-butyldimethylsilyloxy)methyl-3,5-dideoxy-1,2-O-isopropylidene-α-D-allofuranose

: 98-59-9
p-toluenesulfonyl chloride

: 113918-92-6
3-C-(2-benzyloxyethyl)-6-O-(tert-butyldimethylsilyl)-3,5-dideoxy-1,2-O-isopropylidene-5-C-toluenesulfonyloxymethyl-β-L-talofuranose

Guidance literature:: With pyridine; for 18h; Ambient temperature;
DOI:10.1248/cpb.35.2209

Reference yield:

: 58399-55-6
3-deoxy-3-C-<(ethoxycarbonyl)methyl>-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

: 113918-92-6
3-C-(2-benzyloxyethyl)-6-O-(tert-butyldimethylsilyl)-3,5-dideoxy-1,2-O-isopropylidene-5-C-toluenesulfonyloxymethyl-β-L-talofuranose

Guidance literature:: Multi-step reaction with 8 steps

1: LAH / tetrahydrofuran / Ambient temperature

2: NaH / tetrahydrofuran; dimethylsulfoxide / 4 h / Ambient temperature

3: 2percent H₂SO₄ / methanol / 40 h / Ambient temperature

4: imidazole / CH₂Cl₂ / 3 h / 0 °C

5: 1.) oxalyl chloride/DMSO 2.) Et₃N / 1.) CHCl₂, -70 deg C; 2.) CH₂Cl₂, -70 to 0 deg C

6: 84 percent / n-butyllithium / tetrahydrofuran / 1.) room temp., 1 h; 2.) room temp., 3 h

7: 87 percent / B₂H₆ / tetrahydrofuran / 6 h / -5 °C

8: 95 percent / pyridine / 18 h / Ambient temperature

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; sulfuric acid; sodium hydride; dimethyl sulfoxide; triethylamine; diborane; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1248/cpb.35.2209

Reference yield:

: 18427-19-5
1,2;5,6-di-O-isopropylidene-3-(2-hydroxyethyl)-α-D-allofuranoside

: 113918-92-6
3-C-(2-benzyloxyethyl)-6-O-(tert-butyldimethylsilyl)-3,5-dideoxy-1,2-O-isopropylidene-5-C-toluenesulfonyloxymethyl-β-L-talofuranose

Guidance literature:: Multi-step reaction with 7 steps

1: NaH / tetrahydrofuran; dimethylsulfoxide / 4 h / Ambient temperature

2: 2percent H₂SO₄ / methanol / 40 h / Ambient temperature

3: imidazole / CH₂Cl₂ / 3 h / 0 °C

4: 1.) oxalyl chloride/DMSO 2.) Et₃N / 1.) CHCl₂, -70 deg C; 2.) CH₂Cl₂, -70 to 0 deg C

5: 84 percent / n-butyllithium / tetrahydrofuran / 1.) room temp., 1 h; 2.) room temp., 3 h

6: 87 percent / B₂H₆ / tetrahydrofuran / 6 h / -5 °C

7: 95 percent / pyridine / 18 h / Ambient temperature

With pyridine; 1H-imidazole; n-butyllithium; oxalyl dichloride; sulfuric acid; sodium hydride; dimethyl sulfoxide; triethylamine; diborane; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1248/cpb.35.2209