Toluene-4-sulfonic acid (4aR,5aS,6aR,8S,9S,10aS,11aR,13aS)-9-hydroxy-2,2,10a-trimethyl-8-(2-triisopropylsilanyloxy-ethyl)-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-9-ylmethyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (4aR,5aS,6aR,8S,9S,10aS,11aR,13aS)-9-hydroxy-2,2,10a-trimethyl-8-(2-triisopropylsilanyloxy-ethyl)-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-9-ylmethyl ester
CAS No.:315203-96-4
Molecular Formula:C₃₆H₆₀O₁₀SSi
Molecular Weight:713.018
Hs Code.:

Toluene-4-sulfonic acid (4aR,5aS,6aR,8S,9S,10aS,11aR,13aS)-9-hydroxy-2,2,10a-trimethyl-8-(2-triisopropylsilanyloxy-ethyl)-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-9-ylmethyl ester

Synonyms:Toluene-4-sulfonic acid (4aR,5aS,6aR,8S,9S,10aS,11aR,13aS)-9-hydroxy-2,2,10a-trimethyl-8-(2-triisopropylsilanyloxy-ethyl)-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-9-ylmethyl ester

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Chemical Property of Toluene-4-sulfonic acid (4aR,5aS,6aR,8S,9S,10aS,11aR,13aS)-9-hydroxy-2,2,10a-trimethyl-8-(2-triisopropylsilanyloxy-ethyl)-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-9-ylmethyl ester

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Technology Process of Toluene-4-sulfonic acid (4aR,5aS,6aR,8S,9S,10aS,11aR,13aS)-9-hydroxy-2,2,10a-trimethyl-8-(2-triisopropylsilanyloxy-ethyl)-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-9-ylmethyl ester

There total 39 articles about Toluene-4-sulfonic acid (4aR,5aS,6aR,8S,9S,10aS,11aR,13aS)-9-hydroxy-2,2,10a-trimethyl-8-(2-triisopropylsilanyloxy-ethyl)-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-9-ylmethyl 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: 99.0%

: 98-59-9
p-toluenesulfonyl chloride

: 315203-95-3
(4aR,5aS,6aR,8S,9S,10aS,11aR,13aS)-9-Hydroxymethyl-2,2,10a-trimethyl-8-(2-triisopropylsilanyloxy-ethyl)-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-9-ol

: 315203-96-4
Toluene-4-sulfonic acid (4aR,5aS,6aR,8S,9S,10aS,11aR,13aS)-9-hydroxy-2,2,10a-trimethyl-8-(2-triisopropylsilanyloxy-ethyl)-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-9-ylmethyl ester

Guidance literature:: With dmap; In 1,2-dichloro-ethane; at 20 ℃;
DOI:10.1016/S0040-4039(00)01483-0

Reference yield:

: 315203-99-7
(2R,3S,5R,6S)-5-(benzyloxy)-6-(2-(benzyloxy)ethyl)-2-(hydroxymethyl)tetrahydro-2H-pyran-3-ol

: 315203-96-4
Toluene-4-sulfonic acid (4aR,5aS,6aR,8S,9S,10aS,11aR,13aS)-9-hydroxy-2,2,10a-trimethyl-8-(2-triisopropylsilanyloxy-ethyl)-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-9-ylmethyl ester

Guidance literature:: Multi-step reaction with 23 steps

1.1: imidazole / dimethylformamide / 9 h / 50 °C

2.1: 3.11 g / camphorsulfonic acid / methanol; CH₂Cl₂ / 1.33 h / 0 °C

3.1: 95 percent / imidazole; triphenylphosphine; iodine / benzene / 0.42 h / 20 °C

4.1: 96 percent / potassium t-butoxide / tetrahydrofuran / 3 h / 0 °C

5.1: tetrahydrofuran / 3 h / 20 °C

6.1: NaHCO₃; [1,1'-bis(diphenylphosphino)ferrocene]PdCl₂*CH₂Cl₂ / tetrahydrofuran; H₂O; dimethylformamide / 24 h / 20 °C

6.2: 419.6 mg / sodium hydroxide; hydrogen peroxide / tetrahydrofuran; H₂O / 0.5 h / 20 °C

7.1: BH₃*THF / tetrahydrofuran / -30 °C

7.2: 77 percent / sodium hydroxide; hydrogen peroxide / tetrahydrofuran; H₂O / 1.5 h / 20 - 40 °C

8.1: 88 percent / potassium hydride; tetra-n-butylammonium iodide / tetrahydrofuran; various solvent(s) / 1.5 h / 20 °C

9.1: 261 mg / tetra-n-butylammonium fluoride / tetrahydrofuran / 1.5 h / 20 °C

10.1: 94 percent / molecular sieves 4A; tetrapropylammonium perruthenate; N-methylmorpholine N-oxide / CH₂Cl₂ / 1.17 h / 20 °C

11.1: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; phosphate buffer / CH₂Cl₂; H₂O / 0.67 h / 20 °C / pH 7.0

12.1: NaHCO₃; Zn(OTf)2 / CH₂Cl₂ / 20 °C

13.1: 723.1 mg / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 4 h / 20 °C

14.1: 96 percent / m-chloroperbenzoic acid; NaHCO₃ / CH₂Cl₂ / 1.25 h / 20 °C

15.1: 90 percent / CH₂Cl₂; hexane / 5 h / -78 - 20 °C

16.1: sodium methoxide / methanol; CH₂Cl₂ / 0.58 h / 20 °C

17.1: 35.8 mg / pyridinium p-toluenesulfonate / CH₂Cl₂; dimethylformamide / 20 °C

18.1: hydrogen / Pd(OH)2/C / ethyl acetate / 20 °C

19.1: 185.5 mg / imidazole / CH₂Cl₂ / 22 h / 20 °C

20.1: 99 percent / molecular sieves 4A; N-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH₂Cl₂ / 0.5 h / 20 °C

21.1: 92 percent / tetrahydrofuran / 3.5 h / -78 - 20 °C

22.1: N-methylmorpholine N-oxide; OsO₄ / 2-methyl-propan-2-ol; H₂O / 36 h / 20 °C

22.2: 96 percent / NaHSO₃; pyridine / 2-methyl-propan-2-ol; H₂O / 1 h / 20 °C

23.1: 99 percent / 4-(dimethylamino)pyridine / 1,2-dichloro-ethane / 20 °C

With 1H-imidazole; dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; osmium(VIII) oxide; phosphate buffer; tetrapropylammonium perruthennate; borane-THF; 4 A molecular sieve; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; iodine; sodium methylate; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; potassium hydride; zinc trifluoromethanesulfonate; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dihydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 6.1: Suzuki coupling / 21.1: Wittig methylenation;
DOI:10.1016/S0040-4020(01)00164-8

Reference yield:

: 315204-06-9
(4aR,5aS,6aR,8S,9R,10aS,11aR,13aS)-9-Benzyloxy-8-(2-benzyloxy-ethyl)-2,2,10a-trimethyl-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalene

: 315203-96-4
Toluene-4-sulfonic acid (4aR,5aS,6aR,8S,9S,10aS,11aR,13aS)-9-hydroxy-2,2,10a-trimethyl-8-(2-triisopropylsilanyloxy-ethyl)-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-9-ylmethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: hydrogen / Pd(OH)2/C / ethyl acetate / 20 °C

2.1: 185.5 mg / imidazole / CH₂Cl₂ / 22 h / 20 °C

3.1: 99 percent / molecular sieves 4A; N-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH₂Cl₂ / 0.5 h / 20 °C

4.1: 92 percent / tetrahydrofuran / 3.5 h / -78 - 20 °C

5.1: N-methylmorpholine N-oxide; OsO₄ / 2-methyl-propan-2-ol; H₂O / 36 h / 20 °C

5.2: 96 percent / NaHSO₃; pyridine / 2-methyl-propan-2-ol; H₂O / 1 h / 20 °C

6.1: 99 percent / 4-(dimethylamino)pyridine / 1,2-dichloro-ethane / 20 °C

With 1H-imidazole; dmap; osmium(VIII) oxide; tetrapropylammonium perruthennate; 4 A molecular sieve; hydrogen; 4-methylmorpholine N-oxide; palladium dihydroxide; In tetrahydrofuran; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; tert-butyl alcohol; 4.1: Wittig methylenation;
DOI:10.1016/S0040-4020(01)00164-8