(3S,4R)-3-Benzyloxy-4-[(R)-methoxy-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-methoxy]-tetrahydro-furan

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Chemical Name:(3S,4R)-3-Benzyloxy-4-[(R)-methoxy-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-methoxy]-tetrahydro-furan
CAS No.:199122-72-0
Molecular Formula:C₂₁H₂₈O₄
Molecular Weight:344.451
Hs Code.:

Synonyms:(3S,4R)-3-Benzyloxy-4-[(R)-methoxy-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-methoxy]-tetrahydro-furan

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Chemical Property of (3S,4R)-3-Benzyloxy-4-[(R)-methoxy-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-methoxy]-tetrahydro-furan

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Technology Process of (3S,4R)-3-Benzyloxy-4-[(R)-methoxy-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-methoxy]-tetrahydro-furan

There total 6 articles about (3S,4R)-3-Benzyloxy-4-[(R)-methoxy-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-methoxy]-tetrahydro-furan 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: 99.0%

: 100-39-0
benzyl bromide

: 199122-53-7
(3S,4R)-4-[(R)-Methoxy-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-methoxy]-tetrahydro-furan-3-ol

: 199122-72-0
(3S,4R)-3-Benzyloxy-4-[(R)-methoxy-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-methoxy]-tetrahydro-furan

Guidance literature:: With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/ja971881l

Reference yield:

: 153380-53-1
(1R,2R,3S,4S)-3-methylbicyclo[2.2.1]hept-5-en-2-carboxaldehyde

: 199122-72-0
(3S,4R)-3-Benzyloxy-4-[(R)-methoxy-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-methoxy]-tetrahydro-furan

Guidance literature:: Multi-step reaction with 4 steps

1.1: 99 percent / pyridinium p-toluenesulfonate / toluene / 12 h / 20 °C

2.1: 95 percent / γ-collidine; N-bromosuccinimide / acetonitrile / -40 - 20 °C

3.1: 96 percent / MgBr₂*Et₂O; Zn / N,N-dimethyl-acetamide / 12 h / 75 °C

4.1: NaH / tetrahydrofuran; dimethylformamide / 0.5 h / 20 °C

4.2: 99 percent / tetrahydrofuran; dimethylformamide / 24 h / 20 °C

With 2,4,6-trimethyl-pyridine; N-Bromosuccinimide; pyridinium p-toluenesulfonate; sodium hydride; magnesium bromide; zinc; In tetrahydrofuran; N,N-dimethyl acetamide; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/S0040-4020(00)00859-0

Reference yield:

: 94668-49-2
(1R,2R,3S,4S)-3-methyl-5-norbornene-2-methanol

: 199122-72-0
(3S,4R)-3-Benzyloxy-4-[(R)-methoxy-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-methoxy]-tetrahydro-furan

Guidance literature:: Multi-step reaction with 5 steps

1.1: 73 percent / oxalyl chloride; DMSO / CH₂Cl₂ / 1 h / -78 °C

2.1: 99 percent / pyridinium p-toluenesulfonate / toluene / 12 h / 20 °C

3.1: 95 percent / γ-collidine; N-bromosuccinimide / acetonitrile / -40 - 20 °C

4.1: 96 percent / MgBr₂*Et₂O; Zn / N,N-dimethyl-acetamide / 12 h / 75 °C

5.1: NaH / tetrahydrofuran; dimethylformamide / 0.5 h / 20 °C

5.2: 99 percent / tetrahydrofuran; dimethylformamide / 24 h / 20 °C

With 2,4,6-trimethyl-pyridine; N-Bromosuccinimide; oxalyl dichloride; pyridinium p-toluenesulfonate; sodium hydride; dimethyl sulfoxide; magnesium bromide; zinc; In tetrahydrofuran; dichloromethane; N,N-dimethyl acetamide; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: Swern oxidation;
DOI:10.1016/S0040-4020(00)00859-0