Toluene-4-sulfonic acid (R)-4-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-3,5-dimethyl-6-oxo-6H-pyran-2-yl)-2-methoxymethoxy-butyl ester

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Chemical Name:Toluene-4-sulfonic acid (R)-4-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-3,5-dimethyl-6-oxo-6H-pyran-2-yl)-2-methoxymethoxy-butyl ester
CAS No.:140141-15-7
Molecular Formula:C₂₇H₄₂O₉SSi
Molecular Weight:570.777
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (R)-4-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-3,5-dimethyl-6-oxo-6H-pyran-2-yl)-2-methoxymethoxy-butyl ester

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Chemical Property of Toluene-4-sulfonic acid (R)-4-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-3,5-dimethyl-6-oxo-6H-pyran-2-yl)-2-methoxymethoxy-butyl ester

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Technology Process of Toluene-4-sulfonic acid (R)-4-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-3,5-dimethyl-6-oxo-6H-pyran-2-yl)-2-methoxymethoxy-butyl ester

There total 14 articles about Toluene-4-sulfonic acid (R)-4-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-3,5-dimethyl-6-oxo-6H-pyran-2-yl)-2-methoxymethoxy-butyl 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: 72.0%

: 109-87-5
Dimethoxymethane

: 140141-12-4,140141-18-0
Toluene-4-sulfonic acid (R)-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-4-(4-methoxy-3,5-dimethyl-6-oxo-6H-pyran-2-yl)-butyl ester

: 140141-15-7
Toluene-4-sulfonic acid (R)-4-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-3,5-dimethyl-6-oxo-6H-pyran-2-yl)-2-methoxymethoxy-butyl ester

Guidance literature:: With phosphorus pentoxide; In chloroform; at 0 ℃; for 0.166667h;
DOI:10.1016/S0040-4039(00)93985-6

Reference yield:

: 56070-88-3
3,5-dimethyl-6-formyl-4-methoxy-2-pyrone

: 140141-15-7
Toluene-4-sulfonic acid (R)-4-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-3,5-dimethyl-6-oxo-6H-pyran-2-yl)-2-methoxymethoxy-butyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: benzene / 2.3 h / Ambient temperature

2: NaBH₄ / ethanol / 0.33 h / 0 °C

3: 78 percent / L-DET, Ti(OiPr)4, t-BuOOH / CH₂Cl₂ / 3 h / -37 deg C - 30 deg C

4: 100 percent / pyridine / CH₂Cl₂ / 3 h / -35 °C

5: 90 percent / NaI / dimethylformamide / 5 h / 52 °C

6: 79 percent / Zn, AcOH / dimethylformamide / 3.5 h / Ambient temperature

7: 100 percent / imidazole / dimethylformamide / 14 h / Ambient temperature

8: 1.) 9-BBN, 2.) H₂O₂, sat. NaHCO₃ / 1.) THF, 0 deg C to r.t., 1,5 h, 2.) 0 deg C to r.t., 40 min

9: (COCl)2, DMSO, Et₃N / 2 h / -78 °C

10: tetrahydrofuran / 2.5 h / 0 °C

11: 93 percent / OsO₄, 4-methylmorpholine N-oxide / acetonitrile; H₂O / 3.7 h / Ambient temperature

12: 1.) n-Bu₂SnO / 1.) toluene, reflux, 2.5 h, 2.) CHCl₃, r.t., 3 h

13: 72 percent / P₂O₅ / CHCl₃ / 0.17 h / 0 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; osmium(VIII) oxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; diethyl (2R,3R)-tartrate; dihydrogen peroxide; phosphorus pentoxide; di(n-butyl)tin oxide; sodium hydrogencarbonate; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; sodium iodide; zinc; In tetrahydrofuran; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1016/S0040-4039(00)93985-6

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 140141-15-7
Toluene-4-sulfonic acid (R)-4-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-3,5-dimethyl-6-oxo-6H-pyran-2-yl)-2-methoxymethoxy-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / imidazole / dimethylformamide / 14 h / Ambient temperature

2: 1.) 9-BBN, 2.) H₂O₂, sat. NaHCO₃ / 1.) THF, 0 deg C to r.t., 1,5 h, 2.) 0 deg C to r.t., 40 min

3: (COCl)2, DMSO, Et₃N / 2 h / -78 °C

4: tetrahydrofuran / 2.5 h / 0 °C

5: 93 percent / OsO₄, 4-methylmorpholine N-oxide / acetonitrile; H₂O / 3.7 h / Ambient temperature

6: 1.) n-Bu₂SnO / 1.) toluene, reflux, 2.5 h, 2.) CHCl₃, r.t., 3 h

7: 72 percent / P₂O₅ / CHCl₃ / 0.17 h / 0 °C

With 1H-imidazole; osmium(VIII) oxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; dihydrogen peroxide; phosphorus pentoxide; di(n-butyl)tin oxide; sodium hydrogencarbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; chloroform; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4039(00)93985-6