{(R)-1-[(4S,5S)-5-((R)-2-Benzyloxycarbonylamino-propionylamino)-2,2-dimethyl-[1,3]dioxan-4-yl]-2-oxo-ethyl}-carbamic acid benzyl ester

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Chemical Name:{(R)-1-[(4S,5S)-5-((R)-2-Benzyloxycarbonylamino-propionylamino)-2,2-dimethyl-[1,3]dioxan-4-yl]-2-oxo-ethyl}-carbamic acid benzyl ester
CAS No.:81671-19-4
Molecular Formula:C₂₇H₃₃N₃O₈
Molecular Weight:527.574
Hs Code.:

Synonyms:{(R)-1-[(4S,5S)-5-((R)-2-Benzyloxycarbonylamino-propionylamino)-2,2-dimethyl-[1,3]dioxan-4-yl]-2-oxo-ethyl}-carbamic acid benzyl ester

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Chemical Property of {(R)-1-[(4S,5S)-5-((R)-2-Benzyloxycarbonylamino-propionylamino)-2,2-dimethyl-[1,3]dioxan-4-yl]-2-oxo-ethyl}-carbamic acid benzyl ester

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Technology Process of {(R)-1-[(4S,5S)-5-((R)-2-Benzyloxycarbonylamino-propionylamino)-2,2-dimethyl-[1,3]dioxan-4-yl]-2-oxo-ethyl}-carbamic acid benzyl ester

There total 9 articles about {(R)-1-[(4S,5S)-5-((R)-2-Benzyloxycarbonylamino-propionylamino)-2,2-dimethyl-[1,3]dioxan-4-yl]-2-oxo-ethyl}-carbamic acid benzyl 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:

: 81658-15-3
{(S)-1-[(4S,5S)-5-((R)-2-Benzyloxycarbonylamino-propionylamino)-2,2-dimethyl-[1,3]dioxan-4-yl]-2-hydroxy-ethyl}-carbamic acid benzyl ester

: 81671-19-4
{(R)-1-[(4S,5S)-5-((R)-2-Benzyloxycarbonylamino-propionylamino)-2,2-dimethyl-[1,3]dioxan-4-yl]-2-oxo-ethyl}-carbamic acid benzyl ester

Guidance literature:: With pyridine-SO₃ complex; dimethyl sulfoxide; triethylamine; at 20 ℃; for 0.166667h; Yield given;
DOI:10.1016/S0040-4039(00)87057-4

Reference yield:

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

: 81671-19-4
{(R)-1-[(4S,5S)-5-((R)-2-Benzyloxycarbonylamino-propionylamino)-2,2-dimethyl-[1,3]dioxan-4-yl]-2-oxo-ethyl}-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 9 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

8: LiCl-NaBH₄ / ethanol; tetrahydrofuran / 14 h / Ambient temperature

9: SO₃-pyridine, Et₃N, DMSO / 0.17 h / 20 °C

With hydrogenchloride; dmap; sodium tetrahydroborate; pyridine-SO₃ complex; diethyl cyanophosphonate; diphenyl phosphoryl azide; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)87057-4

Reference yield:

: 81658-10-8
5-((S)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-oxazole-4-carboxylic acid methyl ester

: 81671-19-4
{(R)-1-[(4S,5S)-5-((R)-2-Benzyloxycarbonylamino-propionylamino)-2,2-dimethyl-[1,3]dioxan-4-yl]-2-oxo-ethyl}-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 67 percent / 4-N,N-dimethylaminopyridine, Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

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

3: 76.5 percent / diethyl phosphorocyanidate, Et₃N

4: 90.4 percent / LiCl-NaBH₄ / ethanol; tetrahydrofuran / 2.4 h / Ambient temperature

5: 81.5 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 14 h / reflux

6: LiCl-NaBH₄ / ethanol; tetrahydrofuran / 14 h / Ambient temperature

7: SO₃-pyridine, Et₃N, DMSO / 0.17 h / 20 °C

With hydrogenchloride; dmap; sodium tetrahydroborate; pyridine-SO₃ complex; diethyl cyanophosphonate; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1016/S0040-4039(00)87057-4