Acetic acid (2S,5S,6R)-5-methyl-6-((Z)-2-phenylsulfanyl-2-triethylsilanyl-vinyl)-tetrahydro-pyran-2-ylmethyl ester

Base Information

Chemical Name:Acetic acid (2S,5S,6R)-5-methyl-6-((Z)-2-phenylsulfanyl-2-triethylsilanyl-vinyl)-tetrahydro-pyran-2-ylmethyl ester
CAS No.:168333-70-8
Molecular Formula:C₂₃H₃₆O₃SSi
Molecular Weight:420.689
Hs Code.:

Synonyms:Acetic acid (2S,5S,6R)-5-methyl-6-((Z)-2-phenylsulfanyl-2-triethylsilanyl-vinyl)-tetrahydro-pyran-2-ylmethyl ester

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Chemical Property of Acetic acid (2S,5S,6R)-5-methyl-6-((Z)-2-phenylsulfanyl-2-triethylsilanyl-vinyl)-tetrahydro-pyran-2-ylmethyl ester

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Technology Process of Acetic acid (2S,5S,6R)-5-methyl-6-((Z)-2-phenylsulfanyl-2-triethylsilanyl-vinyl)-tetrahydro-pyran-2-ylmethyl ester

There total 1 articles about Acetic acid (2S,5S,6R)-5-methyl-6-((Z)-2-phenylsulfanyl-2-triethylsilanyl-vinyl)-tetrahydro-pyran-2-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: 88.0%

: 617-86-7
triethylsilane

: Acetic acid (2S,5S,6R)-5-methyl-6-phenylsulfanylethynyl-tetrahydro-pyran-2-ylmethyl ester

: 168333-70-8
Acetic acid (2S,5S,6R)-5-methyl-6-((Z)-2-phenylsulfanyl-2-triethylsilanyl-vinyl)-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: With sodium hexachloroplatinate; triethylamine; In isopropyl alcohol; butan-1-ol; at 110 ℃; for 1h;
DOI:10.1016/S0040-4020(97)00229-9

Reference yield: 99.0%

: 168333-70-8
Acetic acid (2S,5S,6R)-5-methyl-6-((Z)-2-phenylsulfanyl-2-triethylsilanyl-vinyl)-tetrahydro-pyran-2-ylmethyl ester

: 168333-71-9
[(2S,5S,6R)-5-Methyl-6-((Z)-2-phenylsulfanyl-2-triethylsilanyl-vinyl)-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: With sodium methylate; In methanol; at 0 ℃; for 1h;
DOI:10.1016/S0040-4020(97)00229-9

Reference yield:

: 168333-70-8
Acetic acid (2S,5S,6R)-5-methyl-6-((Z)-2-phenylsulfanyl-2-triethylsilanyl-vinyl)-tetrahydro-pyran-2-ylmethyl ester

: 168334-04-1
(S)-5-[(2S,3R,6R,8R,9S)-8-((S)-2-Benzenesulfonyl-1-methyl-ethyl)-3,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-3-methyl-pentan-2-one

Guidance literature:: Multi-step reaction with 15 steps

1: 99 percent / NaOMe / methanol / 1 h / 0 °C

2: 94 percent / imidazole / dimethylformamide / 10 h / Ambient temperature

3: 94 percent / MCPBA, Na₂HPO₄ / CH₂Cl₂ / 1 h / Ambient temperature

4: 1.) LiBr, 2.) tetrabutylammonium fluoride / 1.) ether, hexane, -78 deg C, 20 min, 2.) THF, room temperature, 4 h.

5: 95 percent / methyltriphenoxyphosphonium iodide / dimethylformamide / 1 h / Ambient temperature

6: 95 percent / Zn / aq. ethanol; pyridine / 70 °C

7: 80 percent / 2,6-lutidine / CH₂Cl₂ / 2.5 h / Ambient temperature

8: 82 percent / MCPBA, Na₂HPO₄ / CH₂Cl₂ / 5 h / Ambient temperature

9: 1.) n-BuLi, 2.) BF₃*Et₂O / 1.) hexane, THF, -78 deg C, 30 min, 2.) -78 deg C, 2 h.

10: 89 percent / PCC, molecular sieve 4 Angstroem / CH₂Cl₂ / 40 h / Ambient temperature

11: 90 percent / DBU / CH₂Cl₂ / 12 h / 0 °C

12: 91 percent / (triphenylphosphine)copper hydride hexamer / benzene / 40 h / Ambient temperature

13: tetrabutylammonium fluoride / tetrahydrofuran / 5.5 h / 65 °C

14: 70 percent / TsOH*H₂O / CH₂Cl₂ / 24 h / Ambient temperature

15: 85 percent / O₂, CuCl / PdCl₂ / dimethylformamide; H₂O / 40 h / Ambient temperature

With 1H-imidazole; 2,6-dimethylpyridine; disodium hydrogenphosphate; n-butyllithium; hydrido(triphenylphosphine)copper(I) hexamer; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; methyltriphenoxyphosphonium iodide; oxygen; sodium methylate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; copper(l) chloride; lithium bromide; zinc; palladium dichloride; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4020(97)00229-9