(2S,5S)-2-<(tert-butyldiphenylsiloxy)methyl>-7-(p-methoxybenzyl)-1-oxa-7-azaspiro<4.4>non-3-ene-6,9-dione

Base Information

Chemical Name:(2S,5S)-2-<(tert-butyldiphenylsiloxy)methyl>-7-(p-methoxybenzyl)-1-oxa-7-azaspiro<4.4>non-3-ene-6,9-dione
CAS No.:221459-60-5
Molecular Formula:C₃₂H₃₅NO₅Si
Molecular Weight:541.719
Hs Code.:

Synonyms:(2S,5S)-2-<(tert-butyldiphenylsiloxy)methyl>-7-(p-methoxybenzyl)-1-oxa-7-azaspiro<4.4>non-3-ene-6,9-dione

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Chemical Property of (2S,5S)-2-<(tert-butyldiphenylsiloxy)methyl>-7-(p-methoxybenzyl)-1-oxa-7-azaspiro<4.4>non-3-ene-6,9-dione

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Technology Process of (2S,5S)-2-<(tert-butyldiphenylsiloxy)methyl>-7-(p-methoxybenzyl)-1-oxa-7-azaspiro<4.4>non-3-ene-6,9-dione

There total 12 articles about (2S,5S)-2-<(tert-butyldiphenylsiloxy)methyl>-7-(p-methoxybenzyl)-1-oxa-7-azaspiro<4.4>non-3-ene-6,9-dione 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:

: 32780-06-6
(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

: 221459-60-5
(2S,5S)-2-<(tert-butyldiphenylsiloxy)methyl>-7-(p-methoxybenzyl)-1-oxa-7-azaspiro<4.4>non-3-ene-6,9-dione

Guidance literature:: Multi-step reaction with 7 steps

1: 75 percent / imidazole / dimethylformamide / 1.) 20 deg C, 44 h, 2.) 20 to 60 deg C, 4 h

2: 97 percent / Dibal-H / CH₂Cl₂ / 16 h / -78 °C

3: 92 percent / DMAP / pyridine; CH₂Cl₂ / 48 h

4: 2.) t-BuOK / 1.) THF, -78 deg C, 2.) THF, -78 deg C to room temp.

5: 1.) t-BuLi, 2.) BF₃*OEt₂ / 1.) THF, pentane, 2.) THF, pentane, ether

6: 75 percent / pyridinium p-toluenesulfonate / benzene / 4 h / 80 °C

7: NaIO₄, NaHCO₃ / methanol / 12 h / 0 °C

With 1H-imidazole; dmap; sodium periodate; boron trifluoride diethyl etherate; potassium tert-butylate; tert.-butyl lithium; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo982259u

Reference yield:

: 2-(tert-butyl-diphenyl-silanyloxymethyl)-7-(4-methoxy-benzyl)-4-phenylselanyl-1-oxa-7-aza-spiro[4.4]nonane-6,9-dione

: 221459-62-7
(2S,5R)-2-<(tert-butyldiphenylsiloxy)methyl>-7-(p-methoxybenzyl)-1-oxa-7-azaspiro<4.4>non-3-ene-6,9-dione

: 221459-60-5
(2S,5S)-2-<(tert-butyldiphenylsiloxy)methyl>-7-(p-methoxybenzyl)-1-oxa-7-azaspiro<4.4>non-3-ene-6,9-dione

Guidance literature:: With sodium periodate; sodium hydrogencarbonate; In methanol; at 0 ℃; for 12h; Yield given; Yields of byproduct given;
DOI:10.1021/jo982259u

Reference yield:

: 102717-29-3
(5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one

: 221459-60-5
(2S,5S)-2-<(tert-butyldiphenylsiloxy)methyl>-7-(p-methoxybenzyl)-1-oxa-7-azaspiro<4.4>non-3-ene-6,9-dione

Guidance literature:: Multi-step reaction with 6 steps

1: 97 percent / Dibal-H / CH₂Cl₂ / 16 h / -78 °C

2: 92 percent / DMAP / pyridine; CH₂Cl₂ / 48 h

3: 2.) t-BuOK / 1.) THF, -78 deg C, 2.) THF, -78 deg C to room temp.

4: 1.) t-BuLi, 2.) BF₃*OEt₂ / 1.) THF, pentane, 2.) THF, pentane, ether

5: 75 percent / pyridinium p-toluenesulfonate / benzene / 4 h / 80 °C

6: NaIO₄, NaHCO₃ / methanol / 12 h / 0 °C

With dmap; sodium periodate; boron trifluoride diethyl etherate; potassium tert-butylate; tert.-butyl lithium; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; In pyridine; methanol; dichloromethane; benzene;
DOI:10.1021/jo982259u