(γS,2S,5S)-γ-(Benzyloxy)-5-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran-2-propanol

Base Information

Chemical Name:(γS,2S,5S)-γ-(Benzyloxy)-5-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran-2-propanol
CAS No.:170305-58-5
Molecular Formula:C₃₁H₄₀O₄Si
Molecular Weight:504.742
Hs Code.:

Synonyms:(γS,2S,5S)-γ-(Benzyloxy)-5-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran-2-propanol

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Chemical Property of (γS,2S,5S)-γ-(Benzyloxy)-5-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran-2-propanol

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Technology Process of (γS,2S,5S)-γ-(Benzyloxy)-5-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran-2-propanol

There total 8 articles about (γS,2S,5S)-γ-(Benzyloxy)-5-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran-2-propanol 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%

: 170305-57-4
(βS,2S,5S)-β-(Benzyloxy)-5-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran-2-propanal

: 170305-58-5
(γS,2S,5S)-γ-(Benzyloxy)-5-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran-2-propanol

Guidance literature:: With sodium tetrahydroborate; In methanol; for 0.5h;

Reference yield:

: 201472-26-6
(2R/S,5S)-5-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-2-ol

: 170305-58-5
(γS,2S,5S)-γ-(Benzyloxy)-5-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran-2-propanol

Guidance literature:: Multi-step reaction with 8 steps

1: 90 percent / Et₃N / CH₂Cl₂ / 12 h / Ambient temperature

2: 61 percent / BF₃*Et₂O / acetonitrile / 0.17 h / -35 °C

3: 92 percent / NaOMe / 1.5 h / Ambient temperature

4: 86 percent / DIBAH / CH₂Cl₂; hexane / 0.17 h / -78 °C

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

6: 91 percent / NaH / tetrahydrofuran / 1.) 15 min, 2.) r.t., 12 h

7: 1.) O₃, O₂, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2.) -78 deg C to r.t., 1 h

8: 91 percent / NaBH₄ / methanol / 0.5 h

With sodium tetrahydroborate; boron trifluoride diethyl etherate; oxygen; sodium methylate; tin(IV) chloride; sodium hydride; diisobutylaluminium hydride; ozone; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; hexane; dichloromethane; acetonitrile;

Reference yield:

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

: 170305-58-5
(γS,2S,5S)-γ-(Benzyloxy)-5-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran-2-propanol

Guidance literature:: Multi-step reaction with 7 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

6: 1.) O₃, O₂, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2.) -78 deg C to r.t., 1 h

7: 91 percent / NaBH₄ / methanol / 0.5 h

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