(all-S)-<5-(5'-tert-butyldiphenylsiloxymethyltetrahydrofuran-2'-yl)-2-(1''-benzyloxy-3''-buten-1''-yl)>-tetrahydrofuran

Base Information

Chemical Name:(all-S)-<5-(5'-tert-butyldiphenylsiloxymethyltetrahydrofuran-2'-yl)-2-(1''-benzyloxy-3''-buten-1''-yl)>-tetrahydrofuran
CAS No.:157732-27-9
Molecular Formula:C₃₆H₄₆O₄Si
Molecular Weight:570.844
Hs Code.:

Synonyms:(all-S)-<5-(5'-tert-butyldiphenylsiloxymethyltetrahydrofuran-2'-yl)-2-(1''-benzyloxy-3''-buten-1''-yl)>-tetrahydrofuran

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Chemical Property of (all-S)-<5-(5'-tert-butyldiphenylsiloxymethyltetrahydrofuran-2'-yl)-2-(1''-benzyloxy-3''-buten-1''-yl)>-tetrahydrofuran

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Technology Process of (all-S)-<5-(5'-tert-butyldiphenylsiloxymethyltetrahydrofuran-2'-yl)-2-(1''-benzyloxy-3''-buten-1''-yl)>-tetrahydrofuran

There total 2 articles about (all-S)-<5-(5'-tert-butyldiphenylsiloxymethyltetrahydrofuran-2'-yl)-2-(1''-benzyloxy-3''-buten-1''-yl)>-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: 90.0%

: 100-39-0
benzyl bromide

: 1-[(2S,5S,2'S,5'S)-5'-(tert-Butyl-diphenyl-silanyloxymethyl)-octahydro-[2,2']bifuranyl-5-yl]-but-3-en-1-ol

: 157732-27-9
(all-S)-<5-(5'-tert-butyldiphenylsiloxymethyltetrahydrofuran-2'-yl)-2-(1''-benzyloxy-3''-buten-1''-yl)>-tetrahydrofuran

: [(2S,5S,2'S,5'S)-5'-((R)-1-Benzyloxy-but-3-enyl)-octahydro-[2,2']bifuranyl-5-ylmethoxy]-tert-butyl-diphenyl-silane

Guidance literature:: With sodium hydride; In tetrahydrofuran;

Reference yield:

: 157732-26-8
(2S,5S,2'S,5'S)-5-<5'-<(tert-Butyldiphenylsiloxy)methyl>tetrahydrofuran-2'-yl>tetrahydrofuran-2-carboxaldehyde

: 157732-27-9
(all-S)-<5-(5'-tert-butyldiphenylsiloxymethyltetrahydrofuran-2'-yl)-2-(1''-benzyloxy-3''-buten-1''-yl)>-tetrahydrofuran

Guidance literature:: Multi-step reaction with 2 steps

2: NaH / tetrahydrofuran / 6 h / 45 °C

With sodium hydride; In tetrahydrofuran;
DOI:10.1002/chem.19970030723

Reference yield:

: 157732-27-9
(all-S)-<5-(5'-tert-butyldiphenylsiloxymethyltetrahydrofuran-2'-yl)-2-(1''-benzyloxy-3''-buten-1''-yl)>-tetrahydrofuran

: (all-S)-5,5''''-bis(tert-butyldiphenylsiloxymethyl)eicosahydro-<2,2';5',2'';5'',2''';5''',2''''>-pentafuran

Guidance literature:: Multi-step reaction with 11 steps

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

2: 99 percent / NaBH₄ / methanol / 0.5 h

3: 90 percent / pyridine, tri-n-butylphosphine / CH₂Cl₂ / 1 h

4: 76 percent / magnesium monoperoxophthalate / ethanol / 0.5 h / 20 °C

5: LDA / tetrahydrofuran; hexane / 5 h / -78 - 0 °C

6: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -50 deg C, 30 min, 2.) -50 deg C to 0 deg C, 30 min

7: Al/Hg, n-PrOH / tetrahydrofuran

8: 98 percent / NaBH₄ / ethanol / Ambient temperature

9: 81 percent / pyridine / 12 h / 20 °C

10: H₂ / 10percent Pd/C / ethyl acetate / 3 h

11: NaH / tetrahydrofuran / 2 h / 50 °C

With pyridine; propan-1-ol; sodium tetrahydroborate; aluminum amalgam; oxalyl dichloride; tributylphosphine; hydrogen; sodium hydride; magnesium monoperoxyphthalate hexahydrate; ozone; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; ethyl acetate;
DOI:10.1002/chem.19970030723