(1R,2S,4S)-2-<(6S)-t-butyldimethylsilyloxy-1-heptynyl>-4-(2-methoxyethoxymethoxy)-1-cyclopentylmethyl benzyl ether

Base Information

• Chemical Name: (1R,2S,4S)-2-<(6S)-t-butyldimethylsilyloxy-1-heptynyl>-4-(2-methoxyethoxymethoxy)-1-cyclopentylmethyl benzyl ether
• CAS No.: 93929-68-1
• Molecular Formula: C₃₀H₅₀O₅Si
• Molecular Weight: 518.809

Synonyms:(1R,2S,4S)-2-<(6S)-t-butyldimethylsilyloxy-1-heptynyl>-4-(2-methoxyethoxymethoxy)-1-cyclopentylmethyl benzyl ether

Chemical Property of (1R,2S,4S)-2-<(6S)-t-butyldimethylsilyloxy-1-heptynyl>-4-(2-methoxyethoxymethoxy)-1-cyclopentylmethyl benzyl ether

Chemical Property:

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Technology Process of (1R,2S,4S)-2-<(6S)-t-butyldimethylsilyloxy-1-heptynyl>-4-(2-methoxyethoxymethoxy)-1-cyclopentylmethyl benzyl ether

There total 20 articles about (1R,2S,4S)-2-<(6S)-t-butyldimethylsilyloxy-1-heptynyl>-4-(2-methoxyethoxymethoxy)-1-cyclopentylmethyl benzyl ether 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: 82.0%

(1R,2S,4S)-2-ethynyl-4-(2-methoxyethoxymethoxy)-1-cyclopentylmethyl benzyl ether (93929-66-9) + tert-butyl[(1S)-4-iodo-1-methylbutoxy]dimethylsilane (93929-67-0) → (1R,2S,4S)-2-<(6S)-t-butyldimethylsilyloxy-1-heptynyl>-4-(2-methoxyethoxymethoxy)-1-cyclopentylmethyl benzyl ether (93929-68-1)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; for 1h; Ambient temperature;

DOI:10.1016/S0040-4020(01)91304-3

Reference yield:

(2S)-2-methylbutane-1,4-diol (626-95-9,56718-04-8,94799-25-4,24347-57-7) → (1R,2S,4S)-2-<(6S)-t-butyldimethylsilyloxy-1-heptynyl>-4-(2-methoxyethoxymethoxy)-1-cyclopentylmethyl benzyl ether (93929-68-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 23.7 percent / pyridine / Ambient temperature

2: 87 percent / immidazole / dimethylformamide / 16 h / Ambient temperature

3: 85 percent / Na / tetrahydrofuran; liquid ammonia / 1.5 h / -35 - -30 °C

4: 17 g / pyridine / 8 h / 0 °C

5: 74 percent / NaHCO₃, NaI / acetone / 40 h / Heating

6: 82 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 1 h / Ambient temperature

With 1H-imidazole; n-butyllithium; sodium; sodium hydrogencarbonate; sodium iodide; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; ammonia; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4020(01)91304-3

Reference yield:

(S)-5-tosyloxypentan-4-olide (58879-34-8) → (1R,2S,4S)-2-<(6S)-t-butyldimethylsilyloxy-1-heptynyl>-4-(2-methoxyethoxymethoxy)-1-cyclopentylmethyl benzyl ether (93929-68-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 77 percent / LiAlH₄ / tetrahydrofuran / 4 h / Ambient temperature

2: 23.7 percent / pyridine / Ambient temperature

3: 87 percent / immidazole / dimethylformamide / 16 h / Ambient temperature

4: 85 percent / Na / tetrahydrofuran; liquid ammonia / 1.5 h / -35 - -30 °C

5: 17 g / pyridine / 8 h / 0 °C

6: 74 percent / NaHCO₃, NaI / acetone / 40 h / Heating

7: 82 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 1 h / Ambient temperature

With 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; sodium; sodium hydrogencarbonate; sodium iodide; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; ammonia; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4020(01)91304-3

upstream raw materials:

(1R,2S,4S)-2-ethynyl-4-(2-methoxyethoxymethoxy)-1-cyclopentylmethyl benzyl ether

tert-butyl[(1S)-4-iodo-1-methylbutoxy]dimethylsilane

(S)-4-t-butyldimethylsilyloxy-1-trityloxypentane

(2S)-2-methylbutane-1,4-diol

Downstream raw materials:

(+)-brefeldin A

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