(1R,3S,4R)-3-benzyloxy-4-(benzyloxymethyl)-1-tert-butyldimethylsilyloxycyclopentane

Base Information

Chemical Name:(1R,3S,4R)-3-benzyloxy-4-(benzyloxymethyl)-1-tert-butyldimethylsilyloxycyclopentane
CAS No.:1403561-77-2
Molecular Formula:C₂₆H₃₈O₃Si
Molecular Weight:426.671
Hs Code.:

Synonyms:(1R,3S,4R)-3-benzyloxy-4-(benzyloxymethyl)-1-tert-butyldimethylsilyloxycyclopentane

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1R,3S,4R)-3-benzyloxy-4-(benzyloxymethyl)-1-tert-butyldimethylsilyloxycyclopentane

Chemical Property:

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Technology Process of (1R,3S,4R)-3-benzyloxy-4-(benzyloxymethyl)-1-tert-butyldimethylsilyloxycyclopentane

There total 6 articles about (1R,3S,4R)-3-benzyloxy-4-(benzyloxymethyl)-1-tert-butyldimethylsilyloxycyclopentane 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: 91.0%

: 1403561-76-1
(1S,2R,4R)-2-(benzyloxymethyl)-4-tert-butyldimethylsilyloxycyclopentanol

: 100-39-0
benzyl bromide

: 1403561-77-2
(1R,3S,4R)-3-benzyloxy-4-(benzyloxymethyl)-1-tert-butyldimethylsilyloxycyclopentane

Guidance literature:: (1S,2R,4R)-2-(benzyloxymethyl)-4-tert-butyldimethylsilyloxycyclopentanol; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 1h; Inert atmosphere;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; at 20 ℃; Inert atmosphere;
DOI:10.1002/chem.201200733

Reference yield:

: 153186-83-5
(+/-)-3-[(benzyloxy)methyl]cyclopent-3-en-1-ol

: 1403561-77-2
(1R,3S,4R)-3-benzyloxy-4-(benzyloxymethyl)-1-tert-butyldimethylsilyloxycyclopentane

Guidance literature:: Multi-step reaction with 4 steps

1.1: vinyl acetate; pancreatin from porcine pancreas; triethylamine / acetone / 6 h / 20 °C / Enzymatic reaction

2.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

3.1: bis-(1,2-dimethylpropyl)borane / tetrahydrofuran / 48 h / 0 °C

3.2: 0 °C

4.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

4.2: 20 °C / Inert atmosphere

With 1H-imidazole; vinyl acetate; pancreatin from porcine pancreas; bis-(1,2-dimethylpropyl)borane; sodium hydride; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; acetone;
DOI:10.1002/chem.201200733

Reference yield:

: 1403561-38-5
(R)-3-(benzyloxymethyl)cyclopent-3-enyl acetate

: 1403561-77-2
(1R,3S,4R)-3-benzyloxy-4-(benzyloxymethyl)-1-tert-butyldimethylsilyloxycyclopentane

Guidance literature:: Multi-step reaction with 5 steps

1.1: methanol; sodium hydroxide / 2 h / 20 °C

2.1: di-isopropyl azodicarboxylate; triphenylphosphine; benzoic acid / diethyl ether / 16 h / 0 - 20 °C

3.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

4.1: bis-(1,2-dimethylpropyl)borane / tetrahydrofuran / 48 h / 0 °C

4.2: 0 °C

5.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

5.2: 20 °C / Inert atmosphere

With 1H-imidazole; methanol; di-isopropyl azodicarboxylate; bis-(1,2-dimethylpropyl)borane; sodium hydride; triphenylphosphine; benzoic acid; sodium hydroxide; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; 2.1: Mitsunobu reaction;
DOI:10.1002/chem.201200733