N-[(3R,4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-2-oxo-tetrahydro-furan-3-yl]-4-methyl-benzenesulfonamide

Base Information

Chemical Name:N-[(3R,4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-2-oxo-tetrahydro-furan-3-yl]-4-methyl-benzenesulfonamide
CAS No.:174272-16-3
Molecular Formula:C₂₈H₃₃NO₆SSi
Molecular Weight:539.725
Hs Code.:

Synonyms:N-[(3R,4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-2-oxo-tetrahydro-furan-3-yl]-4-methyl-benzenesulfonamide

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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 N-[(3R,4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-2-oxo-tetrahydro-furan-3-yl]-4-methyl-benzenesulfonamide

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Technology Process of N-[(3R,4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-2-oxo-tetrahydro-furan-3-yl]-4-methyl-benzenesulfonamide

There total 5 articles about N-[(3R,4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-2-oxo-tetrahydro-furan-3-yl]-4-methyl-benzenesulfonamide 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: 93.8%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 174272-15-2
(2R,3S,4R)-3-hydroxy-4-hydroxymethyl-2-(p-tolylsulfonamido)-4-butanolide

: 174272-16-3
N-[(3R,4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-2-oxo-tetrahydro-furan-3-yl]-4-methyl-benzenesulfonamide

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 3h; Ambient temperature;
DOI:10.1016/0008-6215(95)00261-8

Reference yield:

: 163356-94-3
1,6-anhydro-3-deoxy-2-O-pivaloyl-3-p-toluenesulfonamido-β-D-altropyranose

: 174272-16-3
N-[(3R,4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-2-oxo-tetrahydro-furan-3-yl]-4-methyl-benzenesulfonamide

Guidance literature:: Multi-step reaction with 5 steps

1: 96.5 percent / p-TsOH*H₂O / toluene / 1 h / Heating

2: 93.5 percent / aq. NaOH / methanol / 13.5 h / Ambient temperature

3: 96.2 percent / (COCl)2, Et₃N / CH₂Cl₂; dimethylsulfoxide / 2.5 h / -78 °C

4: 1.) AcOOH, AcOH, 2.) Me₂S, 3.) conc. HCl

5: 93.8 percent / imidazole / dimethylformamide / 3 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; peracetic acid; sodium hydroxide; oxalyl dichloride; dimethylsulfide; toluene-4-sulfonic acid; acetic acid; triethylamine; In methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
DOI:10.1016/0008-6215(95)00261-8

Reference yield:

: 174272-14-1
1,6-anhydro-3-deoxy-3,4-N,O-isopropylidene-3-(p-tolylsulfonamido)-β-D-ribo-hexopyranos-2-ulose

: 174272-16-3
N-[(3R,4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-2-oxo-tetrahydro-furan-3-yl]-4-methyl-benzenesulfonamide

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) AcOOH, AcOH, 2.) Me₂S, 3.) conc. HCl

2: 93.8 percent / imidazole / dimethylformamide / 3 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; peracetic acid; dimethylsulfide; acetic acid; In N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(95)00261-8