(2S,3S,4S,5S)-3-benzyloxy-2-benzyloxymethyl-2,4-dimethyl-4-dimethylphenylsilyl-5-ethyltetrahydrofuran

Base Information

Chemical Name:(2S,3S,4S,5S)-3-benzyloxy-2-benzyloxymethyl-2,4-dimethyl-4-dimethylphenylsilyl-5-ethyltetrahydrofuran
CAS No.:548487-93-0
Molecular Formula:C₃₁H₄₀O₃Si
Molecular Weight:488.742
Hs Code.:

Synonyms:(2S,3S,4S,5S)-3-benzyloxy-2-benzyloxymethyl-2,4-dimethyl-4-dimethylphenylsilyl-5-ethyltetrahydrofuran

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Chemical Property of (2S,3S,4S,5S)-3-benzyloxy-2-benzyloxymethyl-2,4-dimethyl-4-dimethylphenylsilyl-5-ethyltetrahydrofuran

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Technology Process of (2S,3S,4S,5S)-3-benzyloxy-2-benzyloxymethyl-2,4-dimethyl-4-dimethylphenylsilyl-5-ethyltetrahydrofuran

There total 5 articles about (2S,3S,4S,5S)-3-benzyloxy-2-benzyloxymethyl-2,4-dimethyl-4-dimethylphenylsilyl-5-ethyltetrahydrofuran 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: 96.0%

: 100-39-0
benzyl bromide

: 548488-20-6
(2S,3S,4S,5S)-4-dimethylphenylsilyl-3-hydroxy-2-hydroxymethyl-2,4-dimethyl-5-ethyltetrahydrofuran

: 548487-93-0
(2S,3S,4S,5S)-3-benzyloxy-2-benzyloxymethyl-2,4-dimethyl-4-dimethylphenylsilyl-5-ethyltetrahydrofuran

Guidance literature:: (2S,3S,4S,5S)-4-dimethylphenylsilyl-3-hydroxy-2-hydroxymethyl-2,4-dimethyl-5-ethyltetrahydrofuran; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In hexane; N,N-dimethyl-formamide; at 0 - 23 ℃; for 12h;
DOI:10.1021/ja034865z

Reference yield:

: 768-33-2
phenyldimethylsilyl chloride

: 548487-93-0
(2S,3S,4S,5S)-3-benzyloxy-2-benzyloxymethyl-2,4-dimethyl-4-dimethylphenylsilyl-5-ethyltetrahydrofuran

Guidance literature:: Multi-step reaction with 5 steps

1.1: Li / tetrahydrofuran / 16 h / 23 °C

1.2: CuI / tetrahydrofuran / 4 h / -30 °C

1.3: tetrahydrofuran / 3 h / -78 - -30 °C

2.1: 13.5 g / tetrahydrofuran / 12 h / -30 - 23 °C

3.1: 9.53 g / SnCl₄ / CH₂Cl₂ / 24 h / -78 °C

4.1: 93 percent / LiAlH₄ / tetrahydrofuran / 12 h / 0 °C

5.1: NaH / dimethylformamide / 0.5 h / 0 °C

5.2: 96 percent / n-Bu₄NI / hexane; dimethylformamide / 12 h / 0 - 23 °C

With lithium aluminium tetrahydride; tin(IV) chloride; lithium; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja034865z

Reference yield:

: (E)-3-(Dimethyl-phenyl-silanyl)-2-methyl-pent-1-en-1-ol

: 548487-93-0
(2S,3S,4S,5S)-3-benzyloxy-2-benzyloxymethyl-2,4-dimethyl-4-dimethylphenylsilyl-5-ethyltetrahydrofuran

Guidance literature:: Multi-step reaction with 4 steps

1.1: 13.5 g / tetrahydrofuran / 12 h / -30 - 23 °C

2.1: 9.53 g / SnCl₄ / CH₂Cl₂ / 24 h / -78 °C

3.1: 93 percent / LiAlH₄ / tetrahydrofuran / 12 h / 0 °C

4.1: NaH / dimethylformamide / 0.5 h / 0 °C

4.2: 96 percent / n-Bu₄NI / hexane; dimethylformamide / 12 h / 0 - 23 °C

With lithium aluminium tetrahydride; tin(IV) chloride; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja034865z