(all-S)-4-benzyloxy-1,4-bis-<5'-(5''-tert-butyldiphenylsiloxymethyltetrahydrofuran-2''-yl)-tetrahydrofuran-2'-yl>butanone

Base Information

Chemical Name:(all-S)-4-benzyloxy-1,4-bis-<5'-(5''-tert-butyldiphenylsiloxymethyltetrahydrofuran-2''-yl)-tetrahydrofuran-2'-yl>butanone
CAS No.:157732-29-1
Molecular Formula:C₆₁H₇₈O₈Si₂
Molecular Weight:995.457
Hs Code.:

Synonyms:(all-S)-4-benzyloxy-1,4-bis-<5'-(5''-tert-butyldiphenylsiloxymethyltetrahydrofuran-2''-yl)-tetrahydrofuran-2'-yl>butanone

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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 (all-S)-4-benzyloxy-1,4-bis-<5'-(5''-tert-butyldiphenylsiloxymethyltetrahydrofuran-2''-yl)-tetrahydrofuran-2'-yl>butanone

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Technology Process of (all-S)-4-benzyloxy-1,4-bis-<5'-(5''-tert-butyldiphenylsiloxymethyltetrahydrofuran-2''-yl)-tetrahydrofuran-2'-yl>butanone

There total 11 articles about (all-S)-4-benzyloxy-1,4-bis-<5'-(5''-tert-butyldiphenylsiloxymethyltetrahydrofuran-2''-yl)-tetrahydrofuran-2'-yl>butanone 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:

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

: 157732-29-1
(all-S)-4-benzyloxy-1,4-bis-<5'-(5''-tert-butyldiphenylsiloxymethyltetrahydrofuran-2''-yl)-tetrahydrofuran-2'-yl>butanone

Guidance literature:: Multi-step reaction with 9 steps

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

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

4: 99 percent / NaBH₄ / methanol / 0.5 h

5: 90 percent / pyridine, tri-n-butylphosphine / CH₂Cl₂ / 1 h

6: 76 percent / magnesium monoperoxophthalate / ethanol / 0.5 h / 20 °C

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

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

9: Al/Hg, n-PrOH / tetrahydrofuran

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

Reference yield:

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

: 157732-29-1
(all-S)-4-benzyloxy-1,4-bis-<5'-(5''-tert-butyldiphenylsiloxymethyltetrahydrofuran-2''-yl)-tetrahydrofuran-2'-yl>butanone

Guidance literature:: Multi-step reaction with 8 steps

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

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

3: 99 percent / NaBH₄ / methanol / 0.5 h

4: 90 percent / pyridine, tri-n-butylphosphine / CH₂Cl₂ / 1 h

5: 76 percent / magnesium monoperoxophthalate / ethanol / 0.5 h / 20 °C

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

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

8: Al/Hg, n-PrOH / tetrahydrofuran

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

Reference yield:

: 195731-41-0
(S)-3-Benzyloxy-3-[(2S,5S,2'S,5'S)-5'-(tert-butyl-diphenyl-silanyloxymethyl)-octahydro-[2,2']bifuranyl-5-yl]-propan-1-ol

: 157732-29-1
(all-S)-4-benzyloxy-1,4-bis-<5'-(5''-tert-butyldiphenylsiloxymethyltetrahydrofuran-2''-yl)-tetrahydrofuran-2'-yl>butanone

Guidance literature:: Multi-step reaction with 5 steps

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

2: 76 percent / magnesium monoperoxophthalate / ethanol / 0.5 h / 20 °C

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

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

5: Al/Hg, n-PrOH / tetrahydrofuran

With pyridine; propan-1-ol; aluminum amalgam; oxalyl dichloride; tributylphosphine; magnesium monoperoxyphthalate hexahydrate; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; ethanol; hexane; dichloromethane;
DOI:10.1002/chem.19970030723