(S)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-2,3-dimethyl-5-thioxo-pyrrolidine-2-carbonitrile

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Chemical Name:(S)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-2,3-dimethyl-5-thioxo-pyrrolidine-2-carbonitrile
CAS No.:223663-85-2
Molecular Formula:C₂₇H₃₂N₂O₃S
Molecular Weight:464.629
Hs Code.:

Synonyms:(S)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-2,3-dimethyl-5-thioxo-pyrrolidine-2-carbonitrile

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Chemical Property of (S)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-2,3-dimethyl-5-thioxo-pyrrolidine-2-carbonitrile

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Technology Process of (S)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-2,3-dimethyl-5-thioxo-pyrrolidine-2-carbonitrile

There total 7 articles about (S)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-2,3-dimethyl-5-thioxo-pyrrolidine-2-carbonitrile 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: 98.0%

: (S)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-2,3-dimethyl-5-oxo-pyrrolidine-2-carbonitrile

: 223663-85-2
(S)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-2,3-dimethyl-5-thioxo-pyrrolidine-2-carbonitrile

Guidance literature:: With Lawessons reagent; In toluene; at 80 ℃;
DOI:10.1002/(SICI)1521-3773(19990401)38:7<923::AID-ANIE923>3.0.CO;2-7

Reference yield:

: 5-tert-butoxymethyl-3-methyl-dihydro-furan-2-one

: 223663-85-2
(S)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-2,3-dimethyl-5-thioxo-pyrrolidine-2-carbonitrile

Guidance literature:: Multi-step reaction with 7 steps

1.1: LDA / tetrahydrofuran / -78 °C

1.2: hexamethylphosphoric acid triamide

2.1: TMSOTf / CH₂Cl₂; tetrahydrofuran / 0 °C

3.1: TFA / CH₂Cl₂ / 20 °C

4.1: tetrahydrofuran / -78 °C

5.1: 70 percent

6.1: 70 percent / methanol / 60 °C

7.1: 98 percent / Lawesson's reagent / toluene / 80 °C

With Lawessons reagent; trimethylsilyl trifluoromethanesulfonate; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; toluene; 1.1: Metallation / 1.2: Etherification / 2.1: Substitution / 3.1: Substitution / 4.1: Methylation / 6.1: Addition / 7.1: Substitution;
DOI:10.1002/(SICI)1521-3773(19990401)38:7<923::AID-ANIE923>3.0.CO;2-7

Reference yield:

: 223664-48-0
(5-tert-butoxymethyl-3-methyl-4,5-dihydro-furan-2-yloxy)-tert-butyl-dimethyl-silane

: 223663-85-2
(S)-3-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-2,3-dimethyl-5-thioxo-pyrrolidine-2-carbonitrile

Guidance literature:: Multi-step reaction with 6 steps

1: TMSOTf / CH₂Cl₂; tetrahydrofuran / 0 °C

2: TFA / CH₂Cl₂ / 20 °C

3: tetrahydrofuran / -78 °C

4: 70 percent

5: 70 percent / methanol / 60 °C

6: 98 percent / Lawesson's reagent / toluene / 80 °C

With Lawessons reagent; trimethylsilyl trifluoromethanesulfonate; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; toluene; 1: Substitution / 2: Substitution / 3: Methylation / 5: Addition / 6: Substitution;
DOI:10.1002/(SICI)1521-3773(19990401)38:7<923::AID-ANIE923>3.0.CO;2-7