(1R,2S,3S,6R,7S)-7-Methyl-4-oxo-3-phenylacetylamino-8,10-dioxa-5-aza-tricyclo[5.2.1.0^2,5]decane-6-carboxylic acid methyl ester

Base Information

• Chemical Name: (1R,2S,3S,6R,7S)-7-Methyl-4-oxo-3-phenylacetylamino-8,10-dioxa-5-aza-tricyclo[5.2.1.0^2,5]decane-6-carboxylic acid methyl ester
• CAS No.: 173241-47-9
• Molecular Formula: C₁₈H₂₀N₂O₆
• Molecular Weight: 360.367

Synonyms:(1R,2S,3S,6R,7S)-7-Methyl-4-oxo-3-phenylacetylamino-8,10-dioxa-5-aza-tricyclo[5.2.1.0^2,5]decane-6-carboxylic acid methyl ester

Chemical Property of (1R,2S,3S,6R,7S)-7-Methyl-4-oxo-3-phenylacetylamino-8,10-dioxa-5-aza-tricyclo[5.2.1.0^2,5]decane-6-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (1R,2S,3S,6R,7S)-7-Methyl-4-oxo-3-phenylacetylamino-8,10-dioxa-5-aza-tricyclo[5.2.1.0^2,5]decane-6-carboxylic acid methyl ester

There total 8 articles about (1R,2S,3S,6R,7S)-7-Methyl-4-oxo-3-phenylacetylamino-8,10-dioxa-5-aza-tricyclo[5.2.1.0^2,5]decane-6-carboxylic acid methyl 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:

O-(tert-butyldimethylsilyl)-D-threonine methyl ester → (1R,2S,3S,6R,7S)-7-Methyl-4-oxo-3-phenylacetylamino-8,10-dioxa-5-aza-tricyclo[5.2.1.02,5]decane-6-carboxylic acid methyl ester (173241-47-9)

Guidance literature:

Multi-step reaction with 8 steps

1: MgSO₄ / CH₂Cl₂ / 4 h / 0 °C

2: 90 percent / Et₃N / CH₂Cl₂ / 3 h

3: 87 percent / trifluoroacetic acid / CH₂Cl₂ / 4 h / 14 °C

4: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 2.5 h / Ambient temperature

5: 87 percent / TsOH / tetrahydrofuran; H₂O / 18 h / Heating

6: 48 percent / p-TsOH, silica gel / benzene / 0.42 h / Heating

7: NH₂NH₂*H₂O / 1) CH₃OH, CH₂Cl₂, rt, 3 h; 2) CH₂Cl₂, reflux, 48 h, rt, 48 h

8: NaHCO₃ / H₂O; acetone / Ambient temperature

With silica gel; sodium hydrogencarbonate; magnesium sulfate; Dess-Martin periodane; toluene-4-sulfonic acid; hydrazine hydrate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; acetone; benzene;

DOI:10.1021/jo951651u

Reference yield:

(3S,4S)-1-<1-(methoxycarbonyl)-2-hydroxyprop-1-enyl>-3-phthalimido-4-<(R)-1,2-dihydroxyethyl>azetidin-2-one → (1R,2S,3S,6R,7S)-7-Methyl-4-oxo-3-phenylacetylamino-8,10-dioxa-5-aza-tricyclo[5.2.1.02,5]decane-6-carboxylic acid methyl ester (173241-47-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 48 percent / p-TsOH, silica gel / benzene / 0.42 h / Heating

2: NH₂NH₂*H₂O / 1) CH₃OH, CH₂Cl₂, rt, 3 h; 2) CH₂Cl₂, reflux, 48 h, rt, 48 h

3: NaHCO₃ / H₂O; acetone / Ambient temperature

With silica gel; sodium hydrogencarbonate; toluene-4-sulfonic acid; hydrazine hydrate; In water; acetone; benzene;

DOI:10.1021/jo951651u

Reference yield:

(1R,2S,3S,6R,7S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-7-methyl-4-oxo-8,10-dioxa-5-aza-tricyclo[5.2.1.02,5]decane-6-carboxylic acid methyl ester (173105-17-4) → (1R,2S,3S,6R,7S)-7-Methyl-4-oxo-3-phenylacetylamino-8,10-dioxa-5-aza-tricyclo[5.2.1.02,5]decane-6-carboxylic acid methyl ester (173241-47-9)

Guidance literature:

Multi-step reaction with 2 steps

1: NH₂NH₂*H₂O / 1) CH₃OH, CH₂Cl₂, rt, 3 h; 2) CH₂Cl₂, reflux, 48 h, rt, 48 h

2: NaHCO₃ / H₂O; acetone / Ambient temperature

With sodium hydrogencarbonate; hydrazine hydrate; In water; acetone;

DOI:10.1021/jo951651u

upstream raw materials:

phenylacetyl chloride

(1R,2S,3S,6R,7S)-3-Amino-7-methyl-4-oxo-8,10-dioxa-5-aza-tricyclo[5.2.1.0^2,5]decane-6-carboxylic acid methyl ester

(1R,2S,3S,6R,7S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-7-methyl-4-oxo-8,10-dioxa-5-aza-tricyclo[5.2.1.0^2,5]decane-6-carboxylic acid methyl ester

(3S,4S)-1-<1(R)-(methoxycarbonyl)-2(S)-hydroxypropyl>-3-phthalimido-4-<(R)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one

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