2,4,6-triisopropyl-benzenesulfonic acid (1R)-1-((2R,3aS,5R,6R,10aS)-5-ethyl-6-triethylsilanyloxy-2,3,3a,5,6,7,10,10a-octahydro-furo[3,2-b]oxonin-2-yl)-prop-2-ynyl ester

Base Information

Chemical Name:2,4,6-triisopropyl-benzenesulfonic acid (1R)-1-((2R,3aS,5R,6R,10aS)-5-ethyl-6-triethylsilanyloxy-2,3,3a,5,6,7,10,10a-octahydro-furo[3,2-b]oxonin-2-yl)-prop-2-ynyl ester
CAS No.:441018-95-7
Molecular Formula:C₃₆H₅₈O₆SSi
Molecular Weight:647.004
Hs Code.:

2,4,6-triisopropyl-benzenesulfonic acid (1R)-1-((2R,3aS,5R,6R,10aS)-5-ethyl-6-triethylsilanyloxy-2,3,3a,5,6,7,10,10a-octahydro-furo[3,2-b]oxonin-2-yl)-prop-2-ynyl ester

Synonyms:2,4,6-triisopropyl-benzenesulfonic acid (1R)-1-((2R,3aS,5R,6R,10aS)-5-ethyl-6-triethylsilanyloxy-2,3,3a,5,6,7,10,10a-octahydro-furo[3,2-b]oxonin-2-yl)-prop-2-ynyl ester

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Chemical Property of 2,4,6-triisopropyl-benzenesulfonic acid (1R)-1-((2R,3aS,5R,6R,10aS)-5-ethyl-6-triethylsilanyloxy-2,3,3a,5,6,7,10,10a-octahydro-furo[3,2-b]oxonin-2-yl)-prop-2-ynyl ester

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Technology Process of 2,4,6-triisopropyl-benzenesulfonic acid (1R)-1-((2R,3aS,5R,6R,10aS)-5-ethyl-6-triethylsilanyloxy-2,3,3a,5,6,7,10,10a-octahydro-furo[3,2-b]oxonin-2-yl)-prop-2-ynyl ester

There total 22 articles about 2,4,6-triisopropyl-benzenesulfonic acid (1R)-1-((2R,3aS,5R,6R,10aS)-5-ethyl-6-triethylsilanyloxy-2,3,3a,5,6,7,10,10a-octahydro-furo[3,2-b]oxonin-2-yl)-prop-2-ynyl 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: 96.0%

: 6553-96-4
2,4,6-triisopropylphenylsulfonyl chloride

: 441018-94-6
(1R)-1-((2R,3aS,5R,6R,10aS)-5-ethyl-6-triethylsilanyloxy-2,3,3a,5,6,7,10,10a-octahydro-furo[3,2-b]oxonin-2-yl)-prop-2-yn-1-ol

: 441018-95-7
2,4,6-triisopropyl-benzenesulfonic acid (1R)-1-((2R,3aS,5R,6R,10aS)-5-ethyl-6-triethylsilanyloxy-2,3,3a,5,6,7,10,10a-octahydro-furo[3,2-b]oxonin-2-yl)-prop-2-ynyl ester

Guidance literature:: With dmap; In dichloromethane; for 2.5h; Heating;
DOI:10.1021/ja005892h DOI:10.1016/S0040-4020(02)00040-6

Reference yield:

: 289619-01-8
(4R)-4-benzyl-3-[2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-acetyl]-oxazolidin-2-one

: 441018-95-7
2,4,6-triisopropyl-benzenesulfonic acid (1R)-1-((2R,3aS,5R,6R,10aS)-5-ethyl-6-triethylsilanyloxy-2,3,3a,5,6,7,10,10a-octahydro-furo[3,2-b]oxonin-2-yl)-prop-2-ynyl ester

Guidance literature:: Multi-step reaction with 19 steps

1.1: NaN(SiMe₃)2 / toluene; tetrahydrofuran / 0.5 h / -78 °C

1.2: 75 percent / toluene; tetrahydrofuran / 2 h / -45 °C

2.1: 88 percent / NaBH₄; H₂O / tetrahydrofuran / 5 - 20 °C

3.1: (COCl)2; DMSO / CH₂Cl₂ / 0.42 h / -78 °C

4.1: methoxyborane derived from 3-carene / diethyl ether / 1 h / 20 °C

4.2: diethyl ether / 2 h / -78 °C

4.3: aq. NaOH; aq. H₂O₂ / diethyl ether; tetrahydrofuran / 3 h / 20 °C

5.1: 96 percent / pyridine; 4-dimethylaminopyridine / CH₂Cl₂

6.1: 75 percent / DDQ / CH₂Cl₂; various solvent(s) / pH 7

7.1: 92 percent / NaBH₄ / ethanol / 0.5 h / 0 °C

8.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

9.1: 88 percent / PPTS / CH₂Cl₂; ethanol / 2 h

10.1: 97 percent / (+)-diethyl tartrate; t-BuOOH; Ti(Oi-Pr)4 / CH₂Cl₂ / 40 h / -20 °C

11.1: 94 percent / (Cy₃P)2Cl₂Ru=CHPh / CH₂Cl₂ / 6 h / Heating

12.1: 92 percent / MeOH; K₂CO₃ / 2 h

13.1: aq. sodium periodate / tetrahydrofuran / 0.75 h / pH 7

14.1: 96 percent / CH₂Cl₂ / 16 h / Heating

15.1: 83 percent / i-Bu₂AlH / tetrahydrofuran; hexane / 2.5 h / -78 °C

16.1: 94 percent / (+)-diethyl tartrate; Ti(Oi-Pr)4; t-BuOOH / CH₂Cl₂ / 40 h / -20 °C

17.1: 84 percent / Ph₃P; N-chlorosuccinimide / CH₂Cl₂ / 1 h / Heating

18.1: 87 percent / diisopropylamine; butyl lithium / tetrahydrofuran; hexane / 0.5 h / -30 °C

19.1: 96 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 2.5 h / Heating

With pyridine; 2,6-dimethylpyridine; titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; sodium periodate; N-chloro-succinimide; Grubbs catalyst first generation; n-butyllithium; oxalyl dichloride; methoxyborane derived from 3-carene; water; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; (+)-Weinsaeure-diethylester; diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; toluene; 3.1: Swern oxidation / 10.1: Sharpless asymmetric epoxidation / 16.1: Sharpless epoxidation;
DOI:10.1016/S0040-4020(02)00040-6

Reference yield:

: 441018-90-2
(2R,3aS,5R,6R,10aS)-5-ethyl-6-triethylsilanyloxy-2,3,3a,5,6,7,10,10a-octahydro-furo[3,2-b]oxonine-2-carbaldehyde

: 441018-95-7
2,4,6-triisopropyl-benzenesulfonic acid (1R)-1-((2R,3aS,5R,6R,10aS)-5-ethyl-6-triethylsilanyloxy-2,3,3a,5,6,7,10,10a-octahydro-furo[3,2-b]oxonin-2-yl)-prop-2-ynyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 96 percent / CH₂Cl₂ / 16 h / Heating

2: 83 percent / i-Bu₂AlH / tetrahydrofuran; hexane / 2.5 h / -78 °C

3: 94 percent / (+)-diethyl tartrate; Ti(Oi-Pr)4; t-BuOOH / CH₂Cl₂ / 40 h / -20 °C

4: 84 percent / Ph₃P; N-chlorosuccinimide / CH₂Cl₂ / 1 h / Heating

5: 87 percent / diisopropylamine; butyl lithium / tetrahydrofuran; hexane / 0.5 h / -30 °C

6: 96 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 2.5 h / Heating

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; N-chloro-succinimide; n-butyllithium; diisobutylaluminium hydride; (+)-Weinsaeure-diethylester; diisopropylamine; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; 3: Sharpless epoxidation;
DOI:10.1016/S0040-4020(02)00040-6