(2S,3R,4R,5S,6S)-3,7-bis(tert-butyldimethylsilyloxy)-5-hydroxy-2,4,6-trimethylheptyl-p-nitrobenzoate

Base Information

Chemical Name:(2S,3R,4R,5S,6S)-3,7-bis(tert-butyldimethylsilyloxy)-5-hydroxy-2,4,6-trimethylheptyl-p-nitrobenzoate
CAS No.:765941-34-2
Molecular Formula:C₂₉H₅₃NO₇Si₂
Molecular Weight:583.913
Hs Code.:

Synonyms:(2S,3R,4R,5S,6S)-3,7-bis(tert-butyldimethylsilyloxy)-5-hydroxy-2,4,6-trimethylheptyl-p-nitrobenzoate

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Chemical Property of (2S,3R,4R,5S,6S)-3,7-bis(tert-butyldimethylsilyloxy)-5-hydroxy-2,4,6-trimethylheptyl-p-nitrobenzoate

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Technology Process of (2S,3R,4R,5S,6S)-3,7-bis(tert-butyldimethylsilyloxy)-5-hydroxy-2,4,6-trimethylheptyl-p-nitrobenzoate

There total 13 articles about (2S,3R,4R,5S,6S)-3,7-bis(tert-butyldimethylsilyloxy)-5-hydroxy-2,4,6-trimethylheptyl-p-nitrobenzoate 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: 93.0%

: 765941-29-5
(2S,3R,4R,5S,6S)-3,7-bis(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptane-1,5-diol

: 122-04-3
4-nitro-benzoyl chloride

: 765941-34-2
(2S,3R,4R,5S,6S)-3,7-bis(tert-butyldimethylsilyloxy)-5-hydroxy-2,4,6-trimethylheptyl-p-nitrobenzoate

Guidance literature:: With pyridine; dmap; In dichloromethane; at 20 ℃; for 3h;
DOI:10.1021/jo0492416

Reference yield:

: 765942-01-6
(1R,2S)-1-((1S)-2-tert-butyldimethylsilyloxy-1-methylethyl)-2-methyl-3-butenyl prop-2-enoate

: 765941-34-2
(2S,3R,4R,5S,6S)-3,7-bis(tert-butyldimethylsilyloxy)-5-hydroxy-2,4,6-trimethylheptyl-p-nitrobenzoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: 86 percent / Grubbs' second-generation catalyst / toluene / 3 h / Heating

2.1: 72 percent / NMO; OsO₄ / acetone; H₂O / 6 h / 20 °C

3.1: pyridine / CH₂Cl₂ / 0 °C

4.1: 0.96 g / tributyltin hydride; AIBN / benzene / 5 h / 80 °C

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

5.2: 75 percent / n-butyllithium / hexane; tetrahydrofuran / 16 h / -78 °C

6.1: 78 percent / 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 1 h / -78 °C

7.1: 65 percent / LiBH₄ / tetrahydrofuran / 2 h / 0 °C

8.1: 93 percent / pyridine; DMAP / CH₂Cl₂ / 3 h / 20 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; osmium(VIII) oxide; lithium borohydride; N-methyl-2-indolinone; 2,6-di-tert-butyl-4-methylpyridine; 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

Reference yield:

: 112057-64-4
(R)-3-(tert-butyldimethylsilyloxy)-2-methylpropan-1-ol

: 765941-34-2
(2S,3R,4R,5S,6S)-3,7-bis(tert-butyldimethylsilyloxy)-5-hydroxy-2,4,6-trimethylheptyl-p-nitrobenzoate

Guidance literature:: Multi-step reaction with 11 steps

1.1: 87 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 0 °C

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

2.2: 75 percent / aq. NaOH; H₂O₂ / tetrahydrofuran

3.1: 79 percent / diisopropylethylamine / CH₂Cl₂ / 1 h / 20 °C

4.1: 86 percent / Grubbs' second-generation catalyst / toluene / 3 h / Heating

5.1: 72 percent / NMO; OsO₄ / acetone; H₂O / 6 h / 20 °C

6.1: pyridine / CH₂Cl₂ / 0 °C

7.1: 0.96 g / tributyltin hydride; AIBN / benzene / 5 h / 80 °C

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

8.2: 75 percent / n-butyllithium / hexane; tetrahydrofuran / 16 h / -78 °C

9.1: 78 percent / 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 1 h / -78 °C

10.1: 65 percent / LiBH₄ / tetrahydrofuran / 2 h / 0 °C

11.1: 93 percent / pyridine; DMAP / CH₂Cl₂ / 3 h / 20 °C

With pyridine; (+)-Ipc₂BOMe; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; osmium(VIII) oxide; lithium borohydride; n-butyllithium; N-methyl-2-indolinone; 2,6-di-tert-butyl-4-methylpyridine; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; tri-n-butyl-tin hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 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