Toluene-4-sulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-5-((2S,5S)-5-hydroxy-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-pentyl ester

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Chemical Name:Toluene-4-sulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-5-((2S,5S)-5-hydroxy-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-pentyl ester
CAS No.:226927-00-0
Molecular Formula:C₂₇H₄₈O₇SSi
Molecular Weight:544.825
Hs Code.:

Toluene-4-sulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-5-((2S,5S)-5-hydroxy-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-pentyl ester

Synonyms:Toluene-4-sulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-5-((2S,5S)-5-hydroxy-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-pentyl ester

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Chemical Property of Toluene-4-sulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-5-((2S,5S)-5-hydroxy-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-pentyl ester

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Technology Process of Toluene-4-sulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-5-((2S,5S)-5-hydroxy-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-pentyl ester

There total 7 articles about Toluene-4-sulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-5-((2S,5S)-5-hydroxy-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-pentyl ester 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: 60.0%

: 98-59-9
p-toluenesulfonyl chloride

: 226926-99-4
(R)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-1-((2S,5S)-5-hydroxy-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-pentane-1,5-diol

: 226927-00-0
Toluene-4-sulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-5-((2S,5S)-5-hydroxy-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-pentyl ester

Guidance literature:: With pyridine; In dichloromethane;
DOI:10.1016/S0040-4039(99)00366-4

Reference yield:

: 226926-94-9
Acetic acid (E)-(R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-methyl-hex-3-enyl ester

: 226927-00-0
Toluene-4-sulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-5-((2S,5S)-5-hydroxy-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-pentyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) O₃, 2.) Me₂S, pyridine / 1.) MeOH/CH₂Cl₂, 78 deg C

2: 75 percent / CrCl₂ / tetrahydrofuran / 3 h / 0 °C

3: 40 percent / Cri₉₀₀ NiCl₂ / dimethylsulfoxide / 20 °C

4: 90 percent / NaBH₄, NiCl₂*6H₂O / methanol / 12 h / 0 - 20 °C

5: 90 percent / LiEt₃BH / tetrahydrofuran / 4 h / 60 °C

6: 60 percent / pyridine / CH₂Cl₂

With pyridine; chromium dichloride; sodium tetrahydroborate; dimethylsulfide; Cri₉₀₀ NiCl₂; lithium triethylborohydride; ozone; nickel dichloride; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1016/S0040-4039(99)00366-4

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 226927-00-0
Toluene-4-sulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-5-((2S,5S)-5-hydroxy-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-pentyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 96 percent / imidazole / dimethylformamide / 2.5 h / 20 °C

2: 1.) O₃, 2.) Me₂S, pyridine / 1.) MeOH/CH₂Cl₂, 78 deg C

3: 75 percent / CrCl₂ / tetrahydrofuran / 3 h / 0 °C

4: 40 percent / Cri₉₀₀ NiCl₂ / dimethylsulfoxide / 20 °C

5: 90 percent / NaBH₄, NiCl₂*6H₂O / methanol / 12 h / 0 - 20 °C

6: 90 percent / LiEt₃BH / tetrahydrofuran / 4 h / 60 °C

7: 60 percent / pyridine / CH₂Cl₂

With pyridine; 1H-imidazole; chromium dichloride; sodium tetrahydroborate; dimethylsulfide; Cri₉₀₀ NiCl₂; lithium triethylborohydride; ozone; nickel dichloride; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(99)00366-4