2,2-Dimethyl-propionic acid (S)-2-benzyloxycarbonylamino-2-[(4S,5S)-5-((R)-2-benzyloxycarbonylamino-propionylamino)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethyl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (S)-2-benzyloxycarbonylamino-2-[(4S,5S)-5-((R)-2-benzyloxycarbonylamino-propionylamino)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethyl ester
CAS No.:81658-14-2
Molecular Formula:C₃₂H₄₃N₃O₉
Molecular Weight:613.708
Hs Code.:

2,2-Dimethyl-propionic acid (S)-2-benzyloxycarbonylamino-2-[(4S,5S)-5-((R)-2-benzyloxycarbonylamino-propionylamino)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethyl ester

Synonyms:2,2-Dimethyl-propionic acid (S)-2-benzyloxycarbonylamino-2-[(4S,5S)-5-((R)-2-benzyloxycarbonylamino-propionylamino)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethyl ester

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Chemical Property of 2,2-Dimethyl-propionic acid (S)-2-benzyloxycarbonylamino-2-[(4S,5S)-5-((R)-2-benzyloxycarbonylamino-propionylamino)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethyl ester

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Technology Process of 2,2-Dimethyl-propionic acid (S)-2-benzyloxycarbonylamino-2-[(4S,5S)-5-((R)-2-benzyloxycarbonylamino-propionylamino)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethyl ester

There total 6 articles about 2,2-Dimethyl-propionic acid (S)-2-benzyloxycarbonylamino-2-[(4S,5S)-5-((R)-2-benzyloxycarbonylamino-propionylamino)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethyl 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: 81.5%

: 81689-26-1
2,2-Dimethyl-propionic acid (2S,3S,4S)-2-benzyloxycarbonylamino-4-((R)-2-benzyloxycarbonylamino-propionylamino)-3,5-dihydroxy-pentyl ester

: 77-76-9
2,2-dimethoxy-propane

: 81658-14-2
2,2-Dimethyl-propionic acid (S)-2-benzyloxycarbonylamino-2-[(4S,5S)-5-((R)-2-benzyloxycarbonylamino-propionylamino)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethyl ester

Guidance literature:: With pyridinium p-toluenesulfonate; In dichloromethane; for 14h; reflux;
DOI:10.1016/S0040-4039(00)87057-4

Reference yield:

: 1676-75-1
N-benzyloxycarbonyl-O-t-butyl-L-serine

: 81658-14-2
2,2-Dimethyl-propionic acid (S)-2-benzyloxycarbonylamino-2-[(4S,5S)-5-((R)-2-benzyloxycarbonylamino-propionylamino)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 62 percent / diphenyl phosphorazidate, K₂CO₃ sesquihydrate / dimethylformamide / 1.) 0 deg C, 2 h, 2.) room temp., 14 h

2: trifluoroacetic acid / CH₂Cl₂ / 2 h / Ambient temperature

3: 67 percent / 4-N,N-dimethylaminopyridine, Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

4: 1.) HCl, 2.) NaHCO₃, NaBH₄ / 1.) MeOH, 40 deg C, 2.5 h; 2.) EtOH, -10 deg C, 1 h

5: 76.5 percent / diethyl phosphorocyanidate, Et₃N

6: 90.4 percent / LiCl-NaBH₄ / ethanol; tetrahydrofuran / 2.4 h / Ambient temperature

7: 81.5 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 14 h / reflux

With hydrogenchloride; dmap; sodium tetrahydroborate; diethyl cyanophosphonate; diphenyl phosphoryl azide; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; triethylamine; trifluoroacetic acid; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)87057-4

Reference yield:

: 81658-09-5
5-((S)-1-Benzyloxycarbonylamino-2-tert-butoxy-ethyl)-oxazole-4-carboxylic acid methyl ester

: 81658-14-2
2,2-Dimethyl-propionic acid (S)-2-benzyloxycarbonylamino-2-[(4S,5S)-5-((R)-2-benzyloxycarbonylamino-propionylamino)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: trifluoroacetic acid / CH₂Cl₂ / 2 h / Ambient temperature

2: 67 percent / 4-N,N-dimethylaminopyridine, Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

3: 1.) HCl, 2.) NaHCO₃, NaBH₄ / 1.) MeOH, 40 deg C, 2.5 h; 2.) EtOH, -10 deg C, 1 h

4: 76.5 percent / diethyl phosphorocyanidate, Et₃N

5: 90.4 percent / LiCl-NaBH₄ / ethanol; tetrahydrofuran / 2.4 h / Ambient temperature

6: 81.5 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 14 h / reflux

With hydrogenchloride; dmap; sodium tetrahydroborate; diethyl cyanophosphonate; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; triethylamine; trifluoroacetic acid; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1016/S0040-4039(00)87057-4