(4S)-1,6-anhydro-3,4-dideoxy-4-C-methyl-4-C-p-toluenesulfonyloxyethyl-β-D-threo-hexopyranose

Base Information

Chemical Name:(4S)-1,6-anhydro-3,4-dideoxy-4-C-methyl-4-C-p-toluenesulfonyloxyethyl-β-D-threo-hexopyranose
CAS No.:151982-20-6
Molecular Formula:C₁₆H₂₂O₆S
Molecular Weight:342.413
Hs Code.:

Synonyms:(4S)-1,6-anhydro-3,4-dideoxy-4-C-methyl-4-C-p-toluenesulfonyloxyethyl-β-D-threo-hexopyranose

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Chemical Property of (4S)-1,6-anhydro-3,4-dideoxy-4-C-methyl-4-C-p-toluenesulfonyloxyethyl-β-D-threo-hexopyranose

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Technology Process of (4S)-1,6-anhydro-3,4-dideoxy-4-C-methyl-4-C-p-toluenesulfonyloxyethyl-β-D-threo-hexopyranose

There total 8 articles about (4S)-1,6-anhydro-3,4-dideoxy-4-C-methyl-4-C-p-toluenesulfonyloxyethyl-β-D-threo-hexopyranose 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: 96.0%

: 151982-19-3
(4S)-1,6-anhydro-2-O-tert-butyldimethylsilyl-3,4-dideoxy-4-C-methyl-4-C-p-toluenesulfonyloxyethyl-β-D-threo-hexopyranose

: 151982-20-6
(4S)-1,6-anhydro-3,4-dideoxy-4-C-methyl-4-C-p-toluenesulfonyloxyethyl-β-D-threo-hexopyranose

Guidance literature:: With pyridine hydrogenfluoride; In diethyl ether; for 4h; Ambient temperature;
DOI:10.1248/cpb.41.861

Reference yield:

: 151982-14-8
1,6-anhydro-3,4-dideoxy-4-methyl-β-D-glycero-hex-3-enopyranos-2-ulose

: 151982-20-6
(4S)-1,6-anhydro-3,4-dideoxy-4-C-methyl-4-C-p-toluenesulfonyloxyethyl-β-D-threo-hexopyranose

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) CuI, 2.) HMPA / 1.) THF_. -20 deg C, 15 min, 2.) THF, -78 deg C, 15 min

2: 99 percent / L-Selectride / tetrahydrofuran / 1.5 h / -78 °C

3: 96 percent / imidazole / dimethylformamide / Ambient temperature

4: 1.) 9-borabicyclo<3.3.1>nonane (9-BBN), 2.) 30percent aq. H₂O₂, 3 M aq. NaOH / 1.) THF, RT, 1 h, 2.) THF, 45 deg C, 1 h

5: 93 percent / 4-dimethylaminopyridine (DMAP), pyridine / Ambient temperature

6: 96 percent / HF-pyridine / diethyl ether / 4 h / Ambient temperature

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium hydroxide; copper(l) iodide; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide; L-Selectride; pyridine hydrogenfluoride; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1248/cpb.41.861

Reference yield:

: 151982-18-2
(4S)-1,6-anhydro-2-O-tert-butyldimethylsilyl-3,4-dideoxy-4-C-methyl-4-C-hydroxyethyl-β-D-threo-hexopyranose

: 151982-20-6
(4S)-1,6-anhydro-3,4-dideoxy-4-C-methyl-4-C-p-toluenesulfonyloxyethyl-β-D-threo-hexopyranose

Guidance literature:: Multi-step reaction with 2 steps

1: 93 percent / 4-dimethylaminopyridine (DMAP), pyridine / Ambient temperature

2: 96 percent / HF-pyridine / diethyl ether / 4 h / Ambient temperature

With pyridine; dmap; pyridine hydrogenfluoride; In diethyl ether;
DOI:10.1248/cpb.41.861