(S)-4-benzyl-3-((2S,3S,5R)-5-((S)-1,2-dihydroxyethyl)-5-methyl-2-((1S,3R,5S)-5-methyl-1-((2R,5R)-5-methyl-5-vinyltetrahydrofuran-2-yl)-2,8-dioxabicyclo[3.2.1]octan-3-yl)tetrahydrofuran-3-carbonyl)oxazolidin-2-one

Base Information

Chemical Name:(S)-4-benzyl-3-((2S,3S,5R)-5-((S)-1,2-dihydroxyethyl)-5-methyl-2-((1S,3R,5S)-5-methyl-1-((2R,5R)-5-methyl-5-vinyltetrahydrofuran-2-yl)-2,8-dioxabicyclo[3.2.1]octan-3-yl)tetrahydrofuran-3-carbonyl)oxazolidin-2-one
CAS No.:1291070-05-7
Molecular Formula:C₃₂H₄₃NO₉
Molecular Weight:585.695
Hs Code.:

(S)-4-benzyl-3-((2S,3S,5R)-5-((S)-1,2-dihydroxyethyl)-5-methyl-2-((1S,3R,5S)-5-methyl-1-((2R,5R)-5-methyl-5-vinyltetrahydrofuran-2-yl)-2,8-dioxabicyclo[3.2.1]octan-3-yl)tetrahydrofuran-3-carbonyl)oxazolidin-2-one

Synonyms:(S)-4-benzyl-3-((2S,3S,5R)-5-((S)-1,2-dihydroxyethyl)-5-methyl-2-((1S,3R,5S)-5-methyl-1-((2R,5R)-5-methyl-5-vinyltetrahydrofuran-2-yl)-2,8-dioxabicyclo[3.2.1]octan-3-yl)tetrahydrofuran-3-carbonyl)oxazolidin-2-one

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Chemical Property of (S)-4-benzyl-3-((2S,3S,5R)-5-((S)-1,2-dihydroxyethyl)-5-methyl-2-((1S,3R,5S)-5-methyl-1-((2R,5R)-5-methyl-5-vinyltetrahydrofuran-2-yl)-2,8-dioxabicyclo[3.2.1]octan-3-yl)tetrahydrofuran-3-carbonyl)oxazolidin-2-one

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Technology Process of (S)-4-benzyl-3-((2S,3S,5R)-5-((S)-1,2-dihydroxyethyl)-5-methyl-2-((1S,3R,5S)-5-methyl-1-((2R,5R)-5-methyl-5-vinyltetrahydrofuran-2-yl)-2,8-dioxabicyclo[3.2.1]octan-3-yl)tetrahydrofuran-3-carbonyl)oxazolidin-2-one

There total 23 articles about (S)-4-benzyl-3-((2S,3S,5R)-5-((S)-1,2-dihydroxyethyl)-5-methyl-2-((1S,3R,5S)-5-methyl-1-((2R,5R)-5-methyl-5-vinyltetrahydrofuran-2-yl)-2,8-dioxabicyclo[3.2.1]octan-3-yl)tetrahydrofuran-3-carbonyl)oxazolidin-2-one 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: 53.0%

: 1291070-03-5
(S)-4-benzyl-3-((S,E)-6-hydroxy-2-((S)-hydroxy((1S,3R,5S)-5-methyl-1-((2R,5R)-5-methyl-5-vinyltetrahydrofuran-2-yl)-2,8-dioxabicyclo[3.2.1]octan-3-yl)methyl)-4-methylhex-4-enoyl)oxazolidin-2-one

: 1291070-05-7
(S)-4-benzyl-3-((2S,3S,5R)-5-((S)-1,2-dihydroxyethyl)-5-methyl-2-((1S,3R,5S)-5-methyl-1-((2R,5R)-5-methyl-5-vinyltetrahydrofuran-2-yl)-2,8-dioxabicyclo[3.2.1]octan-3-yl)tetrahydrofuran-3-carbonyl)oxazolidin-2-one

Guidance literature:: With titanium(IV) isopropylate; diethyl (2R,3R)-tartrate; Cumene hydroperoxide; In dichloromethane; at -30 ℃; optical yield given as %de; Inert atmosphere; Molecular sieve;
DOI:10.1021/ol200627d

Reference yield:

: 126-91-0
linalool

: 1291070-05-7
(S)-4-benzyl-3-((2S,3S,5R)-5-((S)-1,2-dihydroxyethyl)-5-methyl-2-((1S,3R,5S)-5-methyl-1-((2R,5R)-5-methyl-5-vinyltetrahydrofuran-2-yl)-2,8-dioxabicyclo[3.2.1]octan-3-yl)tetrahydrofuran-3-carbonyl)oxazolidin-2-one

Guidance literature:: Multi-step reaction with 14 steps

1.1: 2,6-dimethylpyridine / dichloromethane / -78 - 0 °C / Inert atmosphere

2.1: pyridine; ozone / dichloromethane / -78 °C

2.2: 20 °C / Cooling with ice

3.1: 1-(2-(dimethylamino)-ethyl)-3-phenylurea; Nitrosobenzene; L-proline / chloroform / 0.08 h / Inert atmosphere

3.2: 0 °C / Inert atmosphere

3.3: 20 °C / Inert atmosphere

4.1: pyridinium p-toluenesulfonate / N,N-dimethyl-formamide; acetone / 12 h / 20 °C / Inert atmosphere

5.1: 9-bora-bicyclo[3.3.1]nonane / 20 °C / Inert atmosphere

5.2: 6 h / 20 °C / Inert atmosphere

6.1: oxone||potassium monopersulfate triple salt; tetra(n-butyl)ammonium hydrogensulfate; disodium ethylenediaminetetraacetic acid; potassium carbonate; acetic acid; (3aS,4'R,7aS)-2,2,2',2'-tetramethyldihydrospiro[[1,3]dioxolo-[4,5-c]pyran-6,4'-[1,3]dioxolan]-7(7aH)-one; potassium hydroxide / Dimethoxymethane; water; acetonitrile / 3 h / 0 °C / Inert atmosphere

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.75 h / 20 °C / Inert atmosphere; Molecular sieve

8.1: hydrogenchloride / diethyl ether; chloroform / 20 °C / Inert atmosphere

9.1: sulfur trioxide pyridine complex; N-ethyl-N,N-diisopropylamine / dichloromethane; dimethyl sulfoxide / 0 °C / Inert atmosphere

10.1: camphor-10-sulfonic acid / methanol / 20 °C / Inert atmosphere

11.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C / Inert atmosphere

11.2: 0.58 h / Inert atmosphere

12.1: di-n-butylboryl trifluoromethanesulfonate; triethylamine / dichloromethane / -78 - 0 °C / Inert atmosphere

12.2: -78 - 0 °C / Inert atmosphere

12.3: pH 7 / Inert atmosphere; aq. phosphate buffer; Cooling

13.1: camphor-10-sulfonic acid / methanol; dichloromethane / 20 °C / Inert atmosphere

14.1: titanium(IV) isopropylate; diethyl (2R,3R)-tartrate; Cumene hydroperoxide / dichloromethane / -30 °C / Inert atmosphere; Molecular sieve

With pyridine; 2,6-dimethylpyridine; titanium(IV) isopropylate; hydrogenchloride; oxalyl dichloride; diethyl (2R,3R)-tartrate; Cumene hydroperoxide; oxone||potassium monopersulfate triple salt; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; 1-(2-(dimethylamino)-ethyl)-3-phenylurea; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydrogensulfate; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; disodium ethylenediaminetetraacetic acid; potassium carbonate; ozone; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 9-bora-bicyclo[3.3.1]nonane; Nitrosobenzene; (3aS,4'R,7aS)-2,2,2',2'-tetramethyldihydrospiro[[1,3]dioxolo-[4,5-c]pyran-6,4'-[1,3]dioxolan]-7(7aH)-one; L-proline; potassium hydroxide; In tetrahydrofuran; methanol; diethyl ether; Dimethoxymethane; dichloromethane; chloroform; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; acetonitrile; 5.2: Suzuki coupling / 6.1: Shi epoxidation / 12.1: Aldol reaction;
DOI:10.1021/ol200627d

Reference yield:

: 960060-33-7
1-(tert-butyldimethylsilyloxy)-3-methylbut-3-en-2-ol

: 1291070-05-7
(S)-4-benzyl-3-((2S,3S,5R)-5-((S)-1,2-dihydroxyethyl)-5-methyl-2-((1S,3R,5S)-5-methyl-1-((2R,5R)-5-methyl-5-vinyltetrahydrofuran-2-yl)-2,8-dioxabicyclo[3.2.1]octan-3-yl)tetrahydrofuran-3-carbonyl)oxazolidin-2-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: propionic acid / N,N-dimethyl-formamide / 0.67 h / 150 °C / Inert atmosphere; Microwave irradiation; Sealed tube

2.1: lithium hydroxide monohydrate / water; isopropyl alcohol / 0.75 h / 60 °C / Inert atmosphere

2.2: pH 5 - 6 / Inert atmosphere

3.1: triethylamine / tetrahydrofuran / 0 °C / Inert atmosphere

4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

4.2: -78 - 20 °C / Inert atmosphere

5.1: di-n-butylboryl trifluoromethanesulfonate; triethylamine / dichloromethane / -78 - 0 °C / Inert atmosphere

5.2: -78 - 0 °C / Inert atmosphere

5.3: pH 7 / Inert atmosphere; aq. phosphate buffer; Cooling

6.1: camphor-10-sulfonic acid / methanol; dichloromethane / 20 °C / Inert atmosphere

7.1: titanium(IV) isopropylate; diethyl (2R,3R)-tartrate; Cumene hydroperoxide / dichloromethane / -30 °C / Inert atmosphere; Molecular sieve

With titanium(IV) isopropylate; n-butyllithium; lithium hydroxide monohydrate; diethyl (2R,3R)-tartrate; Cumene hydroperoxide; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; propionic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; 5.1: Aldol reaction;
DOI:10.1021/ol200627d