(1R,4E,3aR,7aR)-4-bromomethylene-7a-methyl-1-[(1S)-methyl-2-p-toluenesulfonyloxyethyl]perhydroindene

Base Information

Chemical Name:(1R,4E,3aR,7aR)-4-bromomethylene-7a-methyl-1-[(1S)-methyl-2-p-toluenesulfonyloxyethyl]perhydroindene
CAS No.:173388-39-1
Molecular Formula:C₂₁H₂₉BrO₃S
Molecular Weight:441.429
Hs Code.:

Synonyms:(1R,4E,3aR,7aR)-4-bromomethylene-7a-methyl-1-[(1S)-methyl-2-p-toluenesulfonyloxyethyl]perhydroindene

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Chemical Property of (1R,4E,3aR,7aR)-4-bromomethylene-7a-methyl-1-[(1S)-methyl-2-p-toluenesulfonyloxyethyl]perhydroindene

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Technology Process of (1R,4E,3aR,7aR)-4-bromomethylene-7a-methyl-1-[(1S)-methyl-2-p-toluenesulfonyloxyethyl]perhydroindene

There total 1 articles about (1R,4E,3aR,7aR)-4-bromomethylene-7a-methyl-1-[(1S)-methyl-2-p-toluenesulfonyloxyethyl]perhydroindene 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: 76.0%

: 1034-49-7
(bromomethyl)triphenyl phosphonium bromide

: 342645-83-4
(S)-2-[(1R,3aR,7aR)-octahydro-7a-methyl-4-oxo-4H-inden-1-yl]propyl 4-methylbenzenesulfonate

: 173388-39-1
(1R,4E,3aR,7aR)-4-bromomethylene-7a-methyl-1-[(1S)-methyl-2-p-toluenesulfonyloxyethyl]perhydroindene

Guidance literature:: (bromomethyl)triphenyl phosphonium bromide; With sodium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 1h;

(S)-2-[(1R,3aR,7aR)-octahydro-7a-methyl-4-oxo-4H-inden-1-yl]propyl 4-methylbenzenesulfonate; In tetrahydrofuran; at 0 ℃; for 2h;
DOI:10.1021/ol035922w

Reference yield:

: 173388-39-1
(1R,4E,3aR,7aR)-4-bromomethylene-7a-methyl-1-[(1S)-methyl-2-p-toluenesulfonyloxyethyl]perhydroindene

: (23S,24R)-25-dehydro-1α-hydroxy-24-methylvitamin D₃-26,23-lactone

Guidance literature:: Multi-step reaction with 8 steps

1.1: dimethylsulfoxide / 1.5 h / 70 °C

2.1: 692 mg / DIBAL-H / CH₂Cl₂; toluene / 1.5 h / 0 °C

3.1: CrCl₃; LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

4.1: 93 percent / DIBAL-H / toluene / 0 - 20 °C

5.1: 91 percent / pyridine / CH₂Cl₂ / 16 h / 0 °C

6.1: 93 percent / tetrapropylammonium perruthenate; N-methylmorpholine N-oxide / CH₂Cl₂ / 4 h / 20 °C

7.1: DIBAL-H / toluene / 1.5 h / -78 °C

7.2: 40 percent / MnO₂ / CH₂Cl₂ / 38 h / 20 °C

8.1: Et₃N / Pd(PPh₃)4 / toluene / 1.5 h / 110 °C

8.2: 48 percent / MeOH; (+)-10-camphorsulfonic acid / 1.5 h / 0 - 20 °C

With pyridine; chromium chloride; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene;
DOI:10.1021/ol035922w

Reference yield:

: 173388-39-1
(1R,4E,3aR,7aR)-4-bromomethylene-7a-methyl-1-[(1S)-methyl-2-p-toluenesulfonyloxyethyl]perhydroindene

: (23S,24S)-25-dehydro-1α-hydroxy-24-methylvitamin D₃-26,23-lactone

Guidance literature:: Multi-step reaction with 4 steps

1.1: dimethylsulfoxide / 1.5 h / 70 °C

2.1: 692 mg / DIBAL-H / CH₂Cl₂; toluene / 1.5 h / 0 °C

3.1: CrCl₃; LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

4.1: Et₃N / Pd(PPh₃)4 / toluene / 1.5 h / 110 °C

4.2: 48 percent / MeOH; (+)-10-camphorsulfonic acid / 1.5 h / 0 - 20 °C

With chromium chloride; lithium aluminium tetrahydride; diisobutylaluminium hydride; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene;
DOI:10.1021/ol035922w