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

Base Information

Chemical Name:(4S)-1,6-anhydro-2-O-tert-butyldimethylsilyl-3,4-dideoxy-4-C-methyl-4-C-p-toluenesulfonyloxyethyl-β-D-threo-hexopyranose
CAS No.:151982-19-3
Molecular Formula:C₂₂H₃₆O₆SSi
Molecular Weight:456.676
Hs Code.:

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

Suppliers and Price of (4S)-1,6-anhydro-2-O-tert-butyldimethylsilyl-3,4-dideoxy-4-C-methyl-4-C-p-toluenesulfonyloxyethyl-β-D-threo-hexopyranose

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (4S)-1,6-anhydro-2-O-tert-butyldimethylsilyl-3,4-dideoxy-4-C-methyl-4-C-p-toluenesulfonyloxyethyl-β-D-threo-hexopyranose

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (4S)-1,6-anhydro-2-O-tert-butyldimethylsilyl-3,4-dideoxy-4-C-methyl-4-C-p-toluenesulfonyloxyethyl-β-D-threo-hexopyranose

There total 7 articles about (4S)-1,6-anhydro-2-O-tert-butyldimethylsilyl-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: 93.0%

: 98-59-9
p-toluenesulfonyl chloride

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

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

Guidance literature:: With pyridine; dmap; 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

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

Guidance literature:: Multi-step reaction with 5 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

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; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1248/cpb.41.861

Reference yield:

: 151982-16-0
(4R)-1,6-anhydro-3,4-dideoxy-4-C-methyl-4-C-vinyl-β-D-threo-hexopyranose

: 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

Guidance literature:: Multi-step reaction with 3 steps

1: 96 percent / imidazole / dimethylformamide / Ambient temperature

2: 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

3: 93 percent / 4-dimethylaminopyridine (DMAP), pyridine / Ambient temperature

With pyridine; 1H-imidazole; dmap; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide; In N,N-dimethyl-formamide;
DOI:10.1248/cpb.41.861