(2R,3R,4S,5S)-2-<(tert-butyldiphenylsiloxy)methyl>-3,4-dihydroxy-7-(p-methoxybenzyl)-1-oxa-7-azaspiro<4.4>nonane-6,9-dione, diacetate ester

Base Information

Chemical Name:(2R,3R,4S,5S)-2-<(tert-butyldiphenylsiloxy)methyl>-3,4-dihydroxy-7-(p-methoxybenzyl)-1-oxa-7-azaspiro<4.4>nonane-6,9-dione, diacetate ester
CAS No.:221459-68-3
Molecular Formula:C₃₆H₄₁NO₉Si
Molecular Weight:659.808
Hs Code.:

Synonyms:(2R,3R,4S,5S)-2-<(tert-butyldiphenylsiloxy)methyl>-3,4-dihydroxy-7-(p-methoxybenzyl)-1-oxa-7-azaspiro<4.4>nonane-6,9-dione, diacetate ester

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Chemical Property of (2R,3R,4S,5S)-2-<(tert-butyldiphenylsiloxy)methyl>-3,4-dihydroxy-7-(p-methoxybenzyl)-1-oxa-7-azaspiro<4.4>nonane-6,9-dione, diacetate ester

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Technology Process of (2R,3R,4S,5S)-2-<(tert-butyldiphenylsiloxy)methyl>-3,4-dihydroxy-7-(p-methoxybenzyl)-1-oxa-7-azaspiro<4.4>nonane-6,9-dione, diacetate ester

There total 13 articles about (2R,3R,4S,5S)-2-<(tert-butyldiphenylsiloxy)methyl>-3,4-dihydroxy-7-(p-methoxybenzyl)-1-oxa-7-azaspiro<4.4>nonane-6,9-dione, diacetate ester 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

: 221459-68-3
(2R,3R,4S,5S)-2-<(tert-butyldiphenylsiloxy)methyl>-3,4-dihydroxy-7-(p-methoxybenzyl)-1-oxa-7-azaspiro<4.4>nonane-6,9-dione, diacetate ester

Guidance literature:: Multi-step reaction with 8 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

8: 1.) OsO₄, pyridine, 2.) pyridine, DMAP / 1.) THF, 0 deg C to room temp., 4 h, 2.) CH₂Cl₂, overnight

With pyridine; 1H-imidazole; dmap; sodium periodate; osmium(VIII) oxide; 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:

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

: 221459-68-3
(2R,3R,4S,5S)-2-<(tert-butyldiphenylsiloxy)methyl>-3,4-dihydroxy-7-(p-methoxybenzyl)-1-oxa-7-azaspiro<4.4>nonane-6,9-dione, diacetate ester

Guidance literature:: Multi-step reaction with 7 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

7: 1.) OsO₄, pyridine, 2.) pyridine, DMAP / 1.) THF, 0 deg C to room temp., 4 h, 2.) CH₂Cl₂, overnight

With pyridine; dmap; sodium periodate; osmium(VIII) oxide; 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

Reference yield:

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

: 221459-68-3
(2R,3R,4S,5S)-2-<(tert-butyldiphenylsiloxy)methyl>-3,4-dihydroxy-7-(p-methoxybenzyl)-1-oxa-7-azaspiro<4.4>nonane-6,9-dione, diacetate ester

Guidance literature:: Multi-step reaction with 6 steps

1: 92 percent / DMAP / pyridine; CH₂Cl₂ / 48 h

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

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

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

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

6: 1.) OsO₄, pyridine, 2.) pyridine, DMAP / 1.) THF, 0 deg C to room temp., 4 h, 2.) CH₂Cl₂, overnight

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