4H-Thiopyran-4-one, 3-[(R)-(6S)-1,4-dioxa-8-thiaspiro[4.5]dec-6-ylhydroxymethyl]tetrahydro-, (3S)-

Base Information

Chemical Name:4H-Thiopyran-4-one, 3-[(R)-(6S)-1,4-dioxa-8-thiaspiro[4.5]dec-6-ylhydroxymethyl]tetrahydro-, (3S)-
CAS No.:849343-23-3
Molecular Formula:C13H20O4S2
Molecular Weight:304.42600
Hs Code.:

Synonyms:(S)-3-((R)-(S)-1,4-Dioxa-8-thia-spiro[4.5]dec-6-yl-hydroxy-methyl)-tetrahydro-thiopyran-4-one;(3S)-3-[(R)-(6S)-1,4-dioxa-8-thiaspiro[4.5]dec-6-yl(hydroxy)methyl]tetrahydro-4H-thiopyran-4-one;

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 4H-Thiopyran-4-one, 3-[(R)-(6S)-1,4-dioxa-8-thiaspiro[4.5]dec-6-ylhydroxymethyl]tetrahydro-, (3S)-

Chemical Property:

PSA：106.36000
LogP:1.16570

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Technology Process of 4H-Thiopyran-4-one, 3-[(R)-(6S)-1,4-dioxa-8-thiaspiro[4.5]dec-6-ylhydroxymethyl]tetrahydro-, (3S)-

There total 1 articles about 4H-Thiopyran-4-one, 3-[(R)-(6S)-1,4-dioxa-8-thiaspiro[4.5]dec-6-ylhydroxymethyl]tetrahydro-, (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: 79.0%

: 849343-24-4
(3S)-3-[(R)-(6S)-1,4-dioxa-8-thiaspiro[4.5]dec-6-yl(methoxymethoxy)methyl]tetrahydro-4H-thiopyran-4-one

: 1228104-07-1
(2S,3S,4R,5S,6S)-3-(benzyloxy)-6-(6-ethyl-3,5-dimethyl-4-oxo-4H-pyran-2-yl)-5-(methoxymethoxy)-2,4-dimethylheptanal

: 1228104-14-0
2-((2S,3S,4R,5R,6R,7R)-5-(benzyloxy)-7-hydroxy-3-(methoxymethoxy)-7-((3S,5S)-5-((R)-(methoxymethoxy)((S)-1,4-dioxa-8-thiaspiro[4.5]decan-6-yl)methyl)-4-oxotetrahydro-2H-thiopyran-3-yl)-4,6-dimethylheptan-2-yl)-6-ethyl-3,5-dimethyl-4H-pyran-4-one

: 849343-23-3
(-)-(3S)-3-[(R)-(6S)-1,4-dioxa-8-thiaspiro[4.5]dec-6-yl(triethylsilyloxy)methyl]tetrahydro-4H-thiopyran-4-one

Guidance literature:: (3S)-3-[(R)-(6S)-1,4-dioxa-8-thiaspiro[4.5]dec-6-yl(methoxymethoxy)methyl]tetrahydro-4H-thiopyran-4-one; With titanium tetrachloride; In dichloromethane; at -78 ℃; for 0.0333333h; Inert atmosphere;

With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 1.5h; Inert atmosphere;

(2S,3S,4R,5S,6S)-3-(benzyloxy)-6-(6-ethyl-3,5-dimethyl-4-oxo-4H-pyran-2-yl)-5-(methoxymethoxy)-2,4-dimethylheptanal; In dichloromethane; for 3h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/ja102356j

Reference yield:

: 849343-23-3
(-)-(3S)-3-[(R)-(6S)-1,4-dioxa-8-thiaspiro[4.5]dec-6-yl(triethylsilyloxy)methyl]tetrahydro-4H-thiopyran-4-one

: 72598-35-7
(-)-serricornin

Guidance literature:: Multi-step reaction with 6 steps

1.1: 83 percent / Li(s-Bu)3BH / tetrahydrofuran / 3 h / -78 °C

2.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.17 h / 0 °C

3.1: NaH; imidazole / tetrahydrofuran / 0 - 20 °C

3.2: 93 percent / tetrahydrofuran / 15.5 h / 0 - 20 °C

4.1: 97 percent / Bu₃SnH; AIBN / toluene / 0.5 h / Heating

5.1: 82 percent / Raney nickel W-2 / ethanol / Heating

6.1: AcOH / CH₂Cl₂ / 0.17 h

With 1H-imidazole; 2,6-dimethylpyridine; 2,2'-azobis(isobutyronitrile); Raney nickel W-2; tri-n-butyl-tin hydride; L-Selectride; sodium hydride; acetic acid; In tetrahydrofuran; ethanol; dichloromethane; toluene;
DOI:10.1021/jo061747w

Reference yield:

: 849343-23-3
(-)-(3S)-3-[(R)-(6S)-1,4-dioxa-8-thiaspiro[4.5]dec-6-yl(triethylsilyloxy)methyl]tetrahydro-4H-thiopyran-4-one

: 83997-86-8
serricornin acetate <(4S,6S,7S)-4,6-dimethyl-7-acetoxy-3-nonanone>

Guidance literature:: Multi-step reaction with 7 steps

1.1: 83 percent / Li(s-Bu)3BH / tetrahydrofuran / 3 h / -78 °C

2.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.17 h / 0 °C

3.1: NaH; imidazole / tetrahydrofuran / 0 - 20 °C

3.2: 93 percent / tetrahydrofuran / 15.5 h / 0 - 20 °C

4.1: 97 percent / Bu₃SnH; AIBN / toluene / 0.5 h / Heating

5.1: 82 percent / Raney nickel W-2 / ethanol / Heating

6.1: AcOH / CH₂Cl₂ / 0.17 h

7.1: 31 mg / DMAP / CH₂Cl₂ / 0.25 h

With 1H-imidazole; 2,6-dimethylpyridine; dmap; 2,2'-azobis(isobutyronitrile); Raney nickel W-2; tri-n-butyl-tin hydride; L-Selectride; sodium hydride; acetic acid; In tetrahydrofuran; ethanol; dichloromethane; toluene;
DOI:10.1021/jo061747w