(1S,2R)-1-(tert-butyldimethylsilyloxy)-1-((1S,2S)-2-((1R,2R)-2-(4-methoxybenzyloxy)-1-(methoxymethoxy)propyl)cyclopropyl)-but-3-en-2-yl but-3-enoate

Base Information

• Chemical Name: (1S,2R)-1-(tert-butyldimethylsilyloxy)-1-((1S,2S)-2-((1R,2R)-2-(4-methoxybenzyloxy)-1-(methoxymethoxy)propyl)cyclopropyl)-but-3-en-2-yl but-3-enoate
• CAS No.: 1571901-01-3
• Molecular Formula: C₃₀H₄₈O₇Si
• Molecular Weight: 548.792

Synonyms:(1S,2R)-1-(tert-butyldimethylsilyloxy)-1-((1S,2S)-2-((1R,2R)-2-(4-methoxybenzyloxy)-1-(methoxymethoxy)propyl)cyclopropyl)-but-3-en-2-yl but-3-enoate

Chemical Property of (1S,2R)-1-(tert-butyldimethylsilyloxy)-1-((1S,2S)-2-((1R,2R)-2-(4-methoxybenzyloxy)-1-(methoxymethoxy)propyl)cyclopropyl)-but-3-en-2-yl but-3-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R)-1-(tert-butyldimethylsilyloxy)-1-((1S,2S)-2-((1R,2R)-2-(4-methoxybenzyloxy)-1-(methoxymethoxy)propyl)cyclopropyl)-but-3-en-2-yl but-3-enoate

There total 17 articles about (1S,2R)-1-(tert-butyldimethylsilyloxy)-1-((1S,2S)-2-((1R,2R)-2-(4-methoxybenzyloxy)-1-(methoxymethoxy)propyl)cyclopropyl)-but-3-en-2-yl but-3-enoate 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: 90.0%

but-3-enoic acid (625-38-7) + (1S,2R)-1-(tert-butyldimethylsilyloxy)-1-((1S,2S)-2-((1R,2R)-2-(4-methoxybenzyloxy)-1-(methoxymethoxy)propyl)cyclopropyl)-but-3-en-2-ol (1571900-99-6) → (1S,2R)-1-(tert-butyldimethylsilyloxy)-1-((1S,2S)-2-((1R,2R)-2-(4-methoxybenzyloxy)-1-(methoxymethoxy)propyl)cyclopropyl)-but-3-en-2-yl but-3-enoate (1571901-01-3)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1039/c3ob42367k

Reference yield:

tert-butyl(((1S,2S)-2-((1R,2R)-2-(4-methoxybenzyloxy)-1(methoxymethoxy)propyl)cyclopropyl)methoxy)dimethylsilane (1571900-77-0) → (1S,2R)-1-(tert-butyldimethylsilyloxy)-1-((1S,2S)-2-((1R,2R)-2-(4-methoxybenzyloxy)-1-(methoxymethoxy)propyl)cyclopropyl)-but-3-en-2-yl but-3-enoate (1571901-01-3)

Guidance literature:

Multi-step reaction with 12 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 0 - 20 °C

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.42 h

2.2: 0.42 h / 0 °C

3.1: dichloromethane / 6 h / 20 °C

4.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C

5.1: titanium(IV) isopropylate / dichloromethane / 0.5 h / Inert atmosphere; Molecular sieve

5.2: Inert atmosphere; Molecular sieve

6.1: 1-methyl-1H-imidazole / toluene / 5 h / 20 °C / Inert atmosphere

7.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / -40 °C / Inert atmosphere

8.1: 1H-imidazole / N,N-dimethyl-formamide / 9 h / 20 °C

9.1: methanol; potassium carbonate / 12 h / 20 °C

10.1: N-tosylimidazole; sodium hydride / tetrahydrofuran; mineral oil / 4 h / 0 - 20 °C

11.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -15 °C

11.2: 2 h / 25 °C

12.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 16 h / 20 °C

With 1H-imidazole; 1-methyl-1H-imidazole; titanium(IV) isopropylate; methanol; dmap; n-butyllithium; oxalyl dichloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; dicyclohexyl-carbodiimide; N-tosylimidazole; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil; 2.1: |Swern Oxidation / 2.2: |Swern Oxidation / 3.1: |Wittig Olefination / 12.1: |Steglich Esterification;

DOI:10.1039/c3ob42367k

Reference yield:

(2R,3R,E)-6-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)hex-4-en-3-ol (1571900-72-5) → (1S,2R)-1-(tert-butyldimethylsilyloxy)-1-((1S,2S)-2-((1R,2R)-2-(4-methoxybenzyloxy)-1-(methoxymethoxy)propyl)cyclopropyl)-but-3-en-2-yl but-3-enoate (1571901-01-3)

Guidance literature:

Multi-step reaction with 14 steps

1.1: diethylzinc / dichloromethane; hexane / -78 - 20 °C

2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 0 - 20 °C

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.42 h

4.2: 0.42 h / 0 °C

5.1: dichloromethane / 6 h / 20 °C

6.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C

7.1: titanium(IV) isopropylate / dichloromethane / 0.5 h / Inert atmosphere; Molecular sieve

7.2: Inert atmosphere; Molecular sieve

8.1: 1-methyl-1H-imidazole / toluene / 5 h / 20 °C / Inert atmosphere

9.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / -40 °C / Inert atmosphere

10.1: 1H-imidazole / N,N-dimethyl-formamide / 9 h / 20 °C

11.1: methanol; potassium carbonate / 12 h / 20 °C

12.1: N-tosylimidazole; sodium hydride / tetrahydrofuran; mineral oil / 4 h / 0 - 20 °C

13.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -15 °C

13.2: 2 h / 25 °C

14.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 16 h / 20 °C

With 1H-imidazole; 1-methyl-1H-imidazole; titanium(IV) isopropylate; methanol; dmap; n-butyllithium; oxalyl dichloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; diethylzinc; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; N-tosylimidazole; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil; 1.1: |Simmons-Smith Cyclopropanation / 4.1: |Swern Oxidation / 4.2: |Swern Oxidation / 5.1: |Wittig Olefination / 14.1: |Steglich Esterification;

DOI:10.1039/c3ob42367k

upstream raw materials:

(2R,3R,E)-6-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)hex-4-en-3-ol

(4R,5R,E)-5-(4-methoxybenzyloxy)hex-2-ene-1,4-diol

(R)-(+)-1-(2-furyl)ethanol

(1R,2R)-1-((1S,2S)-2-((tert-butyldimethylsilyloxy)methyl)cyclopropyl)-2-(4-methoxybenzyloxy)propan-1-ol

Downstream raw materials:

(R)-6-((S)-(tert-butyldimethylsilyloxy)((1S,2S)-2-((1R,2R)-2-(4-methoxybenzyloxy)-1-(methoxymethoxy)propyl)cyclopropyl)-methyl)-3,6-dihydro-2H-pyran-2-one

(R)-6-((S)-(tert-butyldimethylsilyloxy)((1S,2S)-2-((1R,2R)-2-(4-methoxybenzyloxy)-1-(methoxymethoxy)propyl)cyclopropyl)-methyl)-5,6-dihydro-2H-pyran-2-one

(E)-((1R,2R)-1-((1S,2S)-2-((S)-(tert-butyldimethylsilyloxy)((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)methyl)cyclopropyl)-1-hydroxypropan-2-yl) 3-(4-methoxyphenyl)acrylate

C₃₀H₄₄O₈Si

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