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

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-ol
CAS No.:1571900-99-6
Molecular Formula:C₂₆H₄₄O₆Si
Molecular Weight:480.717
Hs Code.:

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

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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-ol

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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-ol

There total 15 articles about (1S,2R)-1-(tert-butyldimethylsilyloxy)-1-((1S,2S)-2-((1R,2R)-2-(4-methoxybenzyloxy)-1-(methoxymethoxy)propyl)cyclopropyl)-but-3-en-2-ol 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: 95.0%

: tert-butyl((S)-((1S,2S)-2-((1R,2R)-2-(4-methoxybenzyloxy)-1-(methoxymethoxy)propyl)cyclopropyl)((R)-oxiran-2-yl)methoxy)-dimethylsilane

: 2181-42-2
trimethylsulphonium iodide

: 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-ol

Guidance literature:: trimethylsulphonium iodide; With n-butyllithium; In tetrahydrofuran; hexane; at -15 ℃; for 1h;

tert-butyl((S)-((1S,2S)-2-((1R,2R)-2-(4-methoxybenzyloxy)-1-(methoxymethoxy)propyl)cyclopropyl)((R)-oxiran-2-yl)methoxy)-dimethylsilane; In tetrahydrofuran; hexane; at 25 ℃; for 2h;
DOI:10.1039/c3ob42367k

Reference yield:

: 1571900-72-5
(2R,3R,E)-6-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)hex-4-en-3-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-ol

Guidance literature:: Multi-step reaction with 13 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

With 1H-imidazole; 1-methyl-1H-imidazole; titanium(IV) isopropylate; methanol; 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; 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;
DOI:10.1039/c3ob42367k

Reference yield:

: 1571900-66-7
(4R,5R,E)-5-(4-methoxybenzyloxy)hex-2-ene-1,4-diol

: 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-ol

Guidance literature:: Multi-step reaction with 14 steps

1.1: 1H-imidazole / dichloromethane / 6 h / 0 - 20 °C

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

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

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

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

5.2: 0.42 h / 0 °C

6.1: dichloromethane / 6 h / 20 °C

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

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

8.2: Inert atmosphere; Molecular sieve

9.1: 1-methyl-1H-imidazole / toluene / 5 h / 20 °C / Inert atmosphere

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

11.1: 1H-imidazole / N,N-dimethyl-formamide / 9 h / 20 °C

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

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

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

14.2: 2 h / 25 °C

With 1H-imidazole; 1-methyl-1H-imidazole; titanium(IV) isopropylate; methanol; 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; N-tosylimidazole; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil; 2.1: |Simmons-Smith Cyclopropanation / 5.1: |Swern Oxidation / 5.2: |Swern Oxidation / 6.1: |Wittig Olefination;
DOI:10.1039/c3ob42367k