2-Pentanone, 3-methyl-5-[(2S,3R,6R,8R,9S)-3,9-dimethyl-8-[(1S)-1-methyl-2-(phenyl sulfonyl)ethyl]-1,7-dioxaspiro[5.5]undec-2-yl]-, (3S)-

Base Information

• Chemical Name: 2-Pentanone, 3-methyl-5-[(2S,3R,6R,8R,9S)-3,9-dimethyl-8-[(1S)-1-methyl-2-(phenyl sulfonyl)ethyl]-1,7-dioxaspiro[5.5]undec-2-yl]-, (3S)-
• CAS No.: 168334-04-1
• Molecular Formula: C26H40O5S
• Molecular Weight: 464.65800
• Mol file: 168334-04-1.mol

Synonyms:

Chemical Property of 2-Pentanone, 3-methyl-5-[(2S,3R,6R,8R,9S)-3,9-dimethyl-8-[(1S)-1-methyl-2-(phenyl sulfonyl)ethyl]-1,7-dioxaspiro[5.5]undec-2-yl]-, (3S)-

Chemical Property:

• Boiling Point: 598.1±33.0 °C(Predicted)
• PSA: 78.05000
• Density: 1.13±0.1 g/cm3(Predicted)
• LogP: 6.50900

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Pentanone, 3-methyl-5-[(2S,3R,6R,8R,9S)-3,9-dimethyl-8-[(1S)-1-methyl-2-(phenyl sulfonyl)ethyl]-1,7-dioxaspiro[5.5]undec-2-yl]-, (3S)-

There total 23 articles about 2-Pentanone, 3-methyl-5-[(2S,3R,6R,8R,9S)-3,9-dimethyl-8-[(1S)-1-methyl-2-(phenyl sulfonyl)ethyl]-1,7-dioxaspiro[5.5]undec-2-yl]-, (3S)- 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: 85.0%

(2R,3S,6R,8S,9R)-2-((S)-2-Benzenesulfonyl-1-methyl-ethyl)-3,9-dimethyl-8-((S)-3-methyl-pent-4-enyl)-1,7-dioxa-spiro[5.5]undecane → (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 (168334-04-1)

Guidance literature:

With oxygen; copper(l) chloride; palladium dichloride; In water; N,N-dimethyl-formamide; for 40h; Ambient temperature;

DOI:10.1016/S0040-4020(97)00229-9

Reference yield:

(2S,3R,4S)-1-Benzenesulfonyl-2,4-dimethyl-oct-7-en-3-ol (168333-75-3) → (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 (168334-04-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 80 percent / 2,6-lutidine / CH₂Cl₂ / 2.5 h / Ambient temperature

2: 82 percent / MCPBA, Na₂HPO₄ / CH₂Cl₂ / 5 h / Ambient temperature

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

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

5: 90 percent / DBU / CH₂Cl₂ / 12 h / 0 °C

6: 91 percent / (triphenylphosphine)copper hydride hexamer / benzene / 40 h / Ambient temperature

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

8: 70 percent / TsOH*H₂O / CH₂Cl₂ / 24 h / Ambient temperature

9: 85 percent / O₂, CuCl / PdCl₂ / dimethylformamide; H₂O / 40 h / Ambient temperature

With 2,6-dimethylpyridine; disodium hydrogenphosphate; n-butyllithium; hydrido(triphenylphosphine)copper(I) hexamer; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; oxygen; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; copper(l) chloride; palladium dichloride; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4020(97)00229-9

Reference yield:

(2R,3S,6S)-2-((S)-2-Benzenesulfonyl-1-methyl-ethyl)-6-iodomethyl-3-methyl-tetrahydro-pyran (168333-74-2) → (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 (168334-04-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 95 percent / Zn / aq. ethanol; pyridine / 70 °C

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

3: 82 percent / MCPBA, Na₂HPO₄ / CH₂Cl₂ / 5 h / Ambient temperature

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

5: 89 percent / PCC, molecular sieve 4 Angstroem / CH₂Cl₂ / 40 h / Ambient temperature

6: 90 percent / DBU / CH₂Cl₂ / 12 h / 0 °C

7: 91 percent / (triphenylphosphine)copper hydride hexamer / benzene / 40 h / Ambient temperature

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

9: 70 percent / TsOH*H₂O / CH₂Cl₂ / 24 h / Ambient temperature

10: 85 percent / O₂, CuCl / PdCl₂ / dimethylformamide; H₂O / 40 h / Ambient temperature

With 2,6-dimethylpyridine; disodium hydrogenphosphate; n-butyllithium; hydrido(triphenylphosphine)copper(I) hexamer; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; oxygen; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; copper(l) chloride; zinc; palladium dichloride; In tetrahydrofuran; pyridine; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4020(97)00229-9

upstream raw materials:

(2S,3R,4S)-1-Benzenesulfonyl-2,4-dimethyl-oct-7-en-3-ol

(2R,3S,6S)-2-((S)-2-Benzenesulfonyl-1-methyl-ethyl)-6-iodomethyl-3-methyl-tetrahydro-pyran

[(2S,5S,6R)-6-((S)-2-Benzenesulfonyl-1-methyl-ethyl)-5-methyl-tetrahydro-pyran-2-yl]-methanol

[(1R,2S)-1-((S)-2-Benzenesulfonyl-1-methyl-ethyl)-2-methyl-hex-5-enyloxy]-tert-butyl-dimethyl-silane

Downstream raw materials:

<2S,2(3S),3R,6R,8R,8(1S),9S>-3,9-dimethyl-2-<3-(2-methyl-1,3-dithian-2-yl)butyl>-8-<1-methyl-2-(phenylsulfonyl)ethyl>-1,7-dioxaspiro<5,5>undecane

tautomycin

C₅₉H₁₀₈O₇S₄Si₂

(2S,3S,6R)-6-{(2S,3S,6R,8S,9R)-3,9-Dimethyl-8-[(S)-3-(2-methyl-[1,3]dithian-2-yl)-butyl]-1,7-dioxa-spiro[5.5]undec-2-yl}-2-{2-[(4R,5S,6R)-6-isopropyl-5-methoxy-2-(4-methoxy-phenyl)-[1,3]dioxan-4-ylmethyl]-[1,3]dithian-2-yl}-heptan-3-ol

Refernces