(3R,4S,5R,6S)-6-((2S)-3-benzyloxy-2-tert-butyldimethylsilyloxypropyl)-4-hydroxy-3,5-dimethyltetrahydropyran-2-one

Base Information

Chemical Name:(3R,4S,5R,6S)-6-((2S)-3-benzyloxy-2-tert-butyldimethylsilyloxypropyl)-4-hydroxy-3,5-dimethyltetrahydropyran-2-one
CAS No.:765942-00-5
Molecular Formula:C₂₃H₃₈O₅Si
Molecular Weight:422.637
Hs Code.:

Synonyms:(3R,4S,5R,6S)-6-((2S)-3-benzyloxy-2-tert-butyldimethylsilyloxypropyl)-4-hydroxy-3,5-dimethyltetrahydropyran-2-one

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Chemical Property of (3R,4S,5R,6S)-6-((2S)-3-benzyloxy-2-tert-butyldimethylsilyloxypropyl)-4-hydroxy-3,5-dimethyltetrahydropyran-2-one

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Technology Process of (3R,4S,5R,6S)-6-((2S)-3-benzyloxy-2-tert-butyldimethylsilyloxypropyl)-4-hydroxy-3,5-dimethyltetrahydropyran-2-one

There total 9 articles about (3R,4S,5R,6S)-6-((2S)-3-benzyloxy-2-tert-butyldimethylsilyloxypropyl)-4-hydroxy-3,5-dimethyltetrahydropyran-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:

: 765941-98-8
(2S)-1-benzyloxy-2-tert-butyldimethylsilyloxypent-4-ene

: 765942-00-5
(3R,4S,5R,6S)-6-((2S)-3-benzyloxy-2-tert-butyldimethylsilyloxypropyl)-4-hydroxy-3,5-dimethyltetrahydropyran-2-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: ozone / methanol / -78 °C

1.2: 76 percent / methyl sulfide / methanol / 1 h / 20 °C

2.1: potassium tert-butoxide; n-butyllithium; (+)-B-methoxydiisopinocampheylborane / tetrahydrofuran / 3 h / -78 °C

2.2: 82 percent / aq. NaOH; H₂O₂ / tetrahydrofuran

3.1: 85 percent / triethylamine / CH₂Cl₂ / 1 h / 20 °C

4.1: 96 percent / Grubbs' second-generation catalyst / toluene / 3 h / 120 °C

5.1: 87 percent / NMO; OsO₄ / acetone; H₂O / 6 h / 20 °C

6.1: pyridine / CH₂Cl₂ / 0 °C

7.1: 1.8 g / tributyltin hydride; AIBN / benzene / 5 h / 85 °C

8.1: LDA; hexamethylphosphoramide / tetrahydrofuran; hexane / 2.67 h / -60 °C

8.2: 78 percent / n-butyllithium / hexane; tetrahydrofuran / 16 h / -78 °C

With pyridine; (+)-Ipc₂BOMe; N,N,N,N,N,N-hexamethylphosphoric triamide; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; tri-n-butyl-tin hydride; ozone; triethylamine; lithium diisopropyl amide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; methanol; hexane; dichloromethane; water; acetone; toluene; benzene;
DOI:10.1021/jo0492416

Reference yield:

: 256920-91-9
(2S,4S,5R)-1-benzyloxy-2-tert-butyldimethylsilyloxy-5-methyl-6-hepten-4-ol

: 765942-00-5
(3R,4S,5R,6S)-6-((2S)-3-benzyloxy-2-tert-butyldimethylsilyloxypropyl)-4-hydroxy-3,5-dimethyltetrahydropyran-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 85 percent / triethylamine / CH₂Cl₂ / 1 h / 20 °C

2.1: 96 percent / Grubbs' second-generation catalyst / toluene / 3 h / 120 °C

3.1: 87 percent / NMO; OsO₄ / acetone; H₂O / 6 h / 20 °C

4.1: pyridine / CH₂Cl₂ / 0 °C

5.1: 1.8 g / tributyltin hydride; AIBN / benzene / 5 h / 85 °C

6.1: LDA; hexamethylphosphoramide / tetrahydrofuran; hexane / 2.67 h / -60 °C

6.2: 78 percent / n-butyllithium / hexane; tetrahydrofuran / 16 h / -78 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; osmium(VIII) oxide; N-methyl-2-indolinone; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; triethylamine; lithium diisopropyl amide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; hexane; dichloromethane; water; acetone; toluene; benzene;
DOI:10.1021/jo0492416

Reference yield:

: 765941-99-9
(1S,3S)-1-((1R)-1-methyl-2-propenyl)-4-benzyloxy-3-tert-butyldimethylsilyloxybutyl prop-2-enoate

: 765942-00-5
(3R,4S,5R,6S)-6-((2S)-3-benzyloxy-2-tert-butyldimethylsilyloxypropyl)-4-hydroxy-3,5-dimethyltetrahydropyran-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: 96 percent / Grubbs' second-generation catalyst / toluene / 3 h / 120 °C

2.1: 87 percent / NMO; OsO₄ / acetone; H₂O / 6 h / 20 °C

3.1: pyridine / CH₂Cl₂ / 0 °C

4.1: 1.8 g / tributyltin hydride; AIBN / benzene / 5 h / 85 °C

5.1: LDA; hexamethylphosphoramide / tetrahydrofuran; hexane / 2.67 h / -60 °C

5.2: 78 percent / n-butyllithium / hexane; tetrahydrofuran / 16 h / -78 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; osmium(VIII) oxide; N-methyl-2-indolinone; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; lithium diisopropyl amide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; hexane; dichloromethane; water; acetone; toluene; benzene;
DOI:10.1021/jo0492416