(1S,4R,5R,6S)-5-[(R)-((1R,2S)-2-Benzyloxy-1-vinyl-but-3-enyloxy)-methoxy-methyl]-6-methyl-bicyclo[2.2.1]hept-2-ene

Base Information

• Chemical Name: (1S,4R,5R,6S)-5-[(R)-((1R,2S)-2-Benzyloxy-1-vinyl-but-3-enyloxy)-methoxy-methyl]-6-methyl-bicyclo[2.2.1]hept-2-ene
• CAS No.: 215389-18-7
• Molecular Formula: C₂₃H₃₀O₃
• Molecular Weight: 354.489

Synonyms:(1S,4R,5R,6S)-5-[(R)-((1R,2S)-2-Benzyloxy-1-vinyl-but-3-enyloxy)-methoxy-methyl]-6-methyl-bicyclo[2.2.1]hept-2-ene

Chemical Property of (1S,4R,5R,6S)-5-[(R)-((1R,2S)-2-Benzyloxy-1-vinyl-but-3-enyloxy)-methoxy-methyl]-6-methyl-bicyclo[2.2.1]hept-2-ene

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (1S,4R,5R,6S)-5-[(R)-((1R,2S)-2-Benzyloxy-1-vinyl-but-3-enyloxy)-methoxy-methyl]-6-methyl-bicyclo[2.2.1]hept-2-ene

There total 8 articles about (1S,4R,5R,6S)-5-[(R)-((1R,2S)-2-Benzyloxy-1-vinyl-but-3-enyloxy)-methoxy-methyl]-6-methyl-bicyclo[2.2.1]hept-2-ene 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: 79.0%

benzyl bromide (100-39-0) + (3S,4R)-4-[(R)-Methoxy-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-methoxy]-hexa-1,5-dien-3-ol (249730-05-0) → (1S,4R,5R,6S)-5-[(R)-((1R,2S)-2-Benzyloxy-1-vinyl-but-3-enyloxy)-methoxy-methyl]-6-methyl-bicyclo[2.2.1]hept-2-ene (215389-18-7)

Guidance literature:

(3S,4R)-4-[(R)-Methoxy-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-methoxy]-hexa-1,5-dien-3-ol; With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

benzyl bromide; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 24h;

DOI:10.1016/S0040-4020(00)00859-0

Reference yield:

(1R,2R,3S,4S)-3-methylbicyclo[2.2.1]hept-5-en-2-carboxaldehyde (153380-53-1) → (1S,4R,5R,6S)-5-[(R)-((1R,2S)-2-Benzyloxy-1-vinyl-but-3-enyloxy)-methoxy-methyl]-6-methyl-bicyclo[2.2.1]hept-2-ene (215389-18-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 84 percent / pyridinium p-toluenesulfonate / toluene / 12 h / 20 °C

2.1: 91 percent / γ-collidine; N-bromosuccinimide / acetonitrile / -40 - 20 °C

3.1: 85 percent / ZnCl₂; Zn / N,N-dimethyl-acetamide / 12 h / 75 °C

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

4.2: 79 percent / tetrahydrofuran; dimethylformamide / 24 h / 20 °C

With 2,4,6-trimethyl-pyridine; N-Bromosuccinimide; pyridinium p-toluenesulfonate; sodium hydride; zinc(II) chloride; zinc; In tetrahydrofuran; N,N-dimethyl acetamide; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0040-4020(00)00859-0

Reference yield:

(2S,4R,5S)-2-((1R,2R,3S,4S)-3-Methyl-bicyclo[2.2.1]hept-5-en-2-yl)-4,5-divinyl-[1,3]dioxolane (215389-06-3) → (1S,4R,5R,6S)-5-[(R)-((1R,2S)-2-Benzyloxy-1-vinyl-but-3-enyloxy)-methoxy-methyl]-6-methyl-bicyclo[2.2.1]hept-2-ene (215389-18-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 91 percent / γ-collidine; N-bromosuccinimide / acetonitrile / -40 - 20 °C

2.1: 85 percent / ZnCl₂; Zn / N,N-dimethyl-acetamide / 12 h / 75 °C

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

3.2: 79 percent / tetrahydrofuran; dimethylformamide / 24 h / 20 °C

With 2,4,6-trimethyl-pyridine; N-Bromosuccinimide; sodium hydride; zinc(II) chloride; zinc; In tetrahydrofuran; N,N-dimethyl acetamide; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4020(00)00859-0

upstream raw materials:

benzyl bromide

(1R,2R,3R,5S,6R,8R,9R,10S,12R)-2-Bromo-8-methoxy-12-methyl-5,6-divinyl-4,7-dioxa-tricyclo[7.2.1.0^3,10]dodecane

(3S,4R)-4-[(R)-Methoxy-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-methoxy]-hexa-1,5-dien-3-ol

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

Downstream raw materials:

(2S,4R,5S)-2-((1R,2R,3S,4S)-3-Methyl-bicyclo[2.2.1]hept-5-en-2-yl)-4,5-divinyl-[1,3]dioxolane

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