(1R,4R,5S)-1-((S)-1-Hydroxy-2-methyl-propyl)-2-(4-methoxy-benzyl)-4-methyl-6-oxa-2-aza-bicyclo[3.2.0]heptane-3,7-dione

Base Information

Chemical Name:(1R,4R,5S)-1-((S)-1-Hydroxy-2-methyl-propyl)-2-(4-methoxy-benzyl)-4-methyl-6-oxa-2-aza-bicyclo[3.2.0]heptane-3,7-dione
CAS No.:212772-65-1
Molecular Formula:C₁₈H₂₃NO₅
Molecular Weight:333.384
Hs Code.:

Synonyms:(1R,4R,5S)-1-((S)-1-Hydroxy-2-methyl-propyl)-2-(4-methoxy-benzyl)-4-methyl-6-oxa-2-aza-bicyclo[3.2.0]heptane-3,7-dione

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Chemical Property of (1R,4R,5S)-1-((S)-1-Hydroxy-2-methyl-propyl)-2-(4-methoxy-benzyl)-4-methyl-6-oxa-2-aza-bicyclo[3.2.0]heptane-3,7-dione

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Technology Process of (1R,4R,5S)-1-((S)-1-Hydroxy-2-methyl-propyl)-2-(4-methoxy-benzyl)-4-methyl-6-oxa-2-aza-bicyclo[3.2.0]heptane-3,7-dione

There total 15 articles about (1R,4R,5S)-1-((S)-1-Hydroxy-2-methyl-propyl)-2-(4-methoxy-benzyl)-4-methyl-6-oxa-2-aza-bicyclo[3.2.0]heptane-3,7-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:

: (2R,3S,4R)-3-Hydroxy-2-((S)-1-hydroxy-2-methyl-propyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid

: 212772-65-1
(1R,4R,5S)-1-((S)-1-Hydroxy-2-methyl-propyl)-2-(4-methoxy-benzyl)-4-methyl-6-oxa-2-aza-bicyclo[3.2.0]heptane-3,7-dione

Guidance literature:: With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; In dichloromethane; at 23 ℃; for 0.5h; Yield given;
DOI:10.1002/(SICI)1521-3773(19980703)37:12<1676::AID-ANIE1676>3.0.CO;2-T

Reference yield:

: 20839-80-9
(4-methoxybenzylamino)acetic acid methyl ester

: 212772-65-1
(1R,4R,5S)-1-((S)-1-Hydroxy-2-methyl-propyl)-2-(4-methoxy-benzyl)-4-methyl-6-oxa-2-aza-bicyclo[3.2.0]heptane-3,7-dione

Guidance literature:: Multi-step reaction with 15 steps

1: Et₃N / CH₂Cl₂ / 1 h / 23 °C

2: 93 percent / LDA / tetrahydrofuran / 2 h / -78 °C

3: 90 percent / DBU / 1.) THF, -0 deg C, 15 min, 2.) THF, H₂O, -78 deg C, 0.5 h

4: 95 percent / NaBH(OAc)3 / acetic acid / 1 h / 23 °C

5: 85 percent / pyridine / 10 h / 23 °C

6: 98 percent / 2,6-lutidine / 12 h / 23 °C

7: 92 percent / NaOMe, MeOH / 5 h / 23 °C

8: 82 percent / Raney Ni / ethanol / 1 h / 0 °C

9: 95 percent / Dess-Martin reagent / CH₂Cl₂ / 1 h / 23 °C

10: tetrahydrofuran / 0.5 h / -40 °C

11: NH₄Cl, H₂O / tetrahydrofuran / 0.5 h

12: 99 percent / H₂ / Pd/C / ethanol / 12 h / 23 °C

13: 87 percent / TFA, H₂O / 4 h / 50 °C

14: LiOH, H₂O / tetrahydrofuran / 0.5 h / 23 °C

15: bis(2-oxo-3-oxazolidinyl)phosphinic chloride, Et₃N / CH₂Cl₂ / 0.5 h / 23 °C

With pyridine; 2,6-dimethylpyridine; methanol; lithium hydroxide; water; hydrogen; sodium methylate; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; sodium tris(acetoxy)borohydride; nickel; ammonium chloride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; acetic acid;
DOI:10.1002/(SICI)1521-3773(19980703)37:12<1676::AID-ANIE1676>3.0.CO;2-T

Reference yield:

: N-(4-Methoxy-benzyl)-N-methoxycarbonylmethyl-2-methyl-2-methylsulfanyl-malonamic acid methyl ester

: 212772-65-1
(1R,4R,5S)-1-((S)-1-Hydroxy-2-methyl-propyl)-2-(4-methoxy-benzyl)-4-methyl-6-oxa-2-aza-bicyclo[3.2.0]heptane-3,7-dione

Guidance literature:: Multi-step reaction with 14 steps

1: 93 percent / LDA / tetrahydrofuran / 2 h / -78 °C

2: 90 percent / DBU / 1.) THF, -0 deg C, 15 min, 2.) THF, H₂O, -78 deg C, 0.5 h

3: 95 percent / NaBH(OAc)3 / acetic acid / 1 h / 23 °C

4: 85 percent / pyridine / 10 h / 23 °C

5: 98 percent / 2,6-lutidine / 12 h / 23 °C

6: 92 percent / NaOMe, MeOH / 5 h / 23 °C

7: 82 percent / Raney Ni / ethanol / 1 h / 0 °C

8: 95 percent / Dess-Martin reagent / CH₂Cl₂ / 1 h / 23 °C

9: tetrahydrofuran / 0.5 h / -40 °C

10: NH₄Cl, H₂O / tetrahydrofuran / 0.5 h

11: 99 percent / H₂ / Pd/C / ethanol / 12 h / 23 °C

12: 87 percent / TFA, H₂O / 4 h / 50 °C

13: LiOH, H₂O / tetrahydrofuran / 0.5 h / 23 °C

14: bis(2-oxo-3-oxazolidinyl)phosphinic chloride, Et₃N / CH₂Cl₂ / 0.5 h / 23 °C

With pyridine; 2,6-dimethylpyridine; methanol; lithium hydroxide; water; hydrogen; sodium methylate; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; sodium tris(acetoxy)borohydride; nickel; ammonium chloride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; acetic acid;
DOI:10.1002/(SICI)1521-3773(19980703)37:12<1676::AID-ANIE1676>3.0.CO;2-T