(2S,5S,1'S)-2-<1'-(Benzyloxy)but-3'-enyl>-5-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran

Base Information

Chemical Name:(2S,5S,1'S)-2-<1'-(Benzyloxy)but-3'-enyl>-5-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran
CAS No.:170305-56-3
Molecular Formula:C₃₂H₄₀O₃Si
Molecular Weight:500.753
Hs Code.:

Synonyms:(2S,5S,1'S)-2-<1'-(Benzyloxy)but-3'-enyl>-5-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran

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Chemical Property of (2S,5S,1'S)-2-<1'-(Benzyloxy)but-3'-enyl>-5-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran

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Technology Process of (2S,5S,1'S)-2-<1'-(Benzyloxy)but-3'-enyl>-5-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran

There total 5 articles about (2S,5S,1'S)-2-<1'-(Benzyloxy)but-3'-enyl>-5-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran 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%

: 100-39-0
benzyl bromide

: 170305-55-2
(1S,2'S,5'S)-1-<5'-<(tert-Butyldiphenylsiloxy)methyl>tetrahydrofuran-2'-yl>but-3-en-1-ol

: 170305-56-3
(2S,5S,1'S)-2-<1'-(Benzyloxy)but-3'-enyl>-5-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran

Guidance literature:: With sodium hydride; In tetrahydrofuran; 1.) 15 min, 2.) r.t., 12 h;

Reference yield:

: 201536-71-2
1-acetoxy-2,3-dideoxy-5-O-<(1,1-dimethylethyl)diphenylsilyl>-D-glycero-pentofuranose

: 170305-56-3
(2S,5S,1'S)-2-<1'-(Benzyloxy)but-3'-enyl>-5-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran

Guidance literature:: Multi-step reaction with 5 steps

1: 61 percent / BF₃*Et₂O / acetonitrile / 0.17 h / -35 °C

2: 92 percent / NaOMe / 1.5 h / Ambient temperature

3: 86 percent / DIBAH / CH₂Cl₂; hexane / 0.17 h / -78 °C

4: 93 percent / SnCl₄ / CH₂Cl₂ / 1.) -78 deg C, 3 min, 2.) -78 deg C, 5 min

5: 91 percent / NaH / tetrahydrofuran / 1.) 15 min, 2.) r.t., 12 h

With boron trifluoride diethyl etherate; sodium methylate; tin(IV) chloride; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; acetonitrile;

Reference yield:

: 170305-51-8
Methyl (2S,5S)-5-<(tert-Butyldiphenylsiloxy)methyl>tetrahydrofuran-2-carboxylate

: 170305-56-3
(2S,5S,1'S)-2-<1'-(Benzyloxy)but-3'-enyl>-5-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran

Guidance literature:: Multi-step reaction with 3 steps

1: 86 percent / DIBAH / CH₂Cl₂; hexane / 0.17 h / -78 °C

2: 93 percent / SnCl₄ / CH₂Cl₂ / 1.) -78 deg C, 3 min, 2.) -78 deg C, 5 min

3: 91 percent / NaH / tetrahydrofuran / 1.) 15 min, 2.) r.t., 12 h

With tin(IV) chloride; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane;