[1R,4S,5S,6S,4(1'S)]-[2'-hydroxy-1'-(4-oxo-3-oxa-6-phenylbicyclo[3.1.0]hex-2-yl)ethyl]carbamic acid tert-butyl ester

Base Information

• Chemical Name: [1R,4S,5S,6S,4(1'S)]-[2'-hydroxy-1'-(4-oxo-3-oxa-6-phenylbicyclo[3.1.0]hex-2-yl)ethyl]carbamic acid tert-butyl ester
• CAS No.: 331821-73-9
• Molecular Formula: C₁₈H₂₃NO₅
• Molecular Weight: 333.384

Synonyms:[1R,4S,5S,6S,4(1'S)]-[2'-hydroxy-1'-(4-oxo-3-oxa-6-phenylbicyclo[3.1.0]hex-2-yl)ethyl]carbamic acid tert-butyl ester

Chemical Property of [1R,4S,5S,6S,4(1'S)]-[2'-hydroxy-1'-(4-oxo-3-oxa-6-phenylbicyclo[3.1.0]hex-2-yl)ethyl]carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [1R,4S,5S,6S,4(1'S)]-[2'-hydroxy-1'-(4-oxo-3-oxa-6-phenylbicyclo[3.1.0]hex-2-yl)ethyl]carbamic acid tert-butyl ester

There total 8 articles about [1R,4S,5S,6S,4(1'S)]-[2'-hydroxy-1'-(4-oxo-3-oxa-6-phenylbicyclo[3.1.0]hex-2-yl)ethyl]carbamic acid tert-butyl 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:

phenylacetylene (536-74-3) → [1R,4S,5S,6S,4(1'S)]-[2'-hydroxy-1'-(4-oxo-3-oxa-6-phenylbicyclo[3.1.0]hex-2-yl)ethyl]carbamic acid tert-butyl ester (331821-73-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: n-BuLi; 18-crown-6 / tetrahydrofuran; hexane / 1.17 h / -78 °C

1.2: 8 percent / tetrahydrofuran; hexane / 2.25 h / -78 °C

2.1: 78 percent / Red-Al / diethyl ether / 0.92 h / 0 - 20 °C

3.1: N,N-dimethylaniline / CH₂Cl₂ / 0.25 h / 0 °C

4.1: Et₃N / CH₂Cl₂ / 0.42 h / 0 - 20 °C

5.1: 71 percent / Cu(TBS)2 / toluene / Heating

6.1: aq. HCl; triethylsilane / dioxane / 1 h

7.1: 2.61 g / Et₃N / acetonitrile / 12 h / 20 °C

With hydrogenchloride; triethylsilane; n-butyllithium; 18-crown-6 ether; N,N-dimethyl-aniline; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; Cu(TBS)2; In tetrahydrofuran; 1,4-dioxane; diethyl ether; hexane; dichloromethane; toluene; acetonitrile;

DOI:10.1021/jo001257i

Reference yield:

trans-[4S,4(1'S)]-4-(1'-hydroxy-3'-phenyl-2'-propenyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (154437-23-7) → [1R,4S,5S,6S,4(1'S)]-[2'-hydroxy-1'-(4-oxo-3-oxa-6-phenylbicyclo[3.1.0]hex-2-yl)ethyl]carbamic acid tert-butyl ester (331821-73-9)

Guidance literature:

Multi-step reaction with 5 steps

1: N,N-dimethylaniline / CH₂Cl₂ / 0.25 h / 0 °C

2: Et₃N / CH₂Cl₂ / 0.42 h / 0 - 20 °C

3: 71 percent / Cu(TBS)2 / toluene / Heating

4: aq. HCl; triethylsilane / dioxane / 1 h

5: 2.61 g / Et₃N / acetonitrile / 12 h / 20 °C

With hydrogenchloride; triethylsilane; N,N-dimethyl-aniline; triethylamine; Cu(TBS)2; In 1,4-dioxane; dichloromethane; toluene; acetonitrile;

DOI:10.1021/jo001257i

Reference yield:

tert-butyl (4S)-4-<(1S)-1-hydroxy-3-phenyl-2-propynyl>-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (241478-34-2) → [1R,4S,5S,6S,4(1'S)]-[2'-hydroxy-1'-(4-oxo-3-oxa-6-phenylbicyclo[3.1.0]hex-2-yl)ethyl]carbamic acid tert-butyl ester (331821-73-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 78 percent / Red-Al / diethyl ether / 0.92 h / 0 - 20 °C

2: N,N-dimethylaniline / CH₂Cl₂ / 0.25 h / 0 °C

3: Et₃N / CH₂Cl₂ / 0.42 h / 0 - 20 °C

4: 71 percent / Cu(TBS)2 / toluene / Heating

5: aq. HCl; triethylsilane / dioxane / 1 h

6: 2.61 g / Et₃N / acetonitrile / 12 h / 20 °C

With hydrogenchloride; triethylsilane; N,N-dimethyl-aniline; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; Cu(TBS)2; In 1,4-dioxane; diethyl ether; dichloromethane; toluene; acetonitrile;

DOI:10.1021/jo001257i

upstream raw materials:

di-tert-butyl dicarbonate

phenylacetylene

trans-[4S,4(1'S)]-4-(1'-hydroxy-3'-phenyl-2'-propenyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

tert-butyl (4S)-4-<(1S)-1-hydroxy-3-phenyl-2-propynyl>-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Downstream raw materials:

(R)-4-((S)-1-{(S)-(tert-Butyl-dimethyl-silanyloxy)-[(1S,2R,3S)-2-((S)-1-methoxycarbonyl-3-methylsulfanyl-propylcarbamoyl)-3-phenyl-cyclopropyl]-methyl}-propylcarbamoyl)-2,2-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester

(R)-4-{(S)-1-[(S)-(tert-Butyl-dimethyl-silanyloxy)-((1S,2R,3S)-2-carboxy-3-phenyl-cyclopropyl)-methyl]-propylcarbamoyl}-2,2-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester

(R)-4-{(S)-1-[(S)-(tert-Butyl-dimethyl-silanyloxy)-((1S,2R,3S)-2-methoxycarbonyl-3-phenyl-cyclopropyl)-methyl]-propylcarbamoyl}-2,2-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester

(R)-2,2-Dimethyl-4-[(S)-1-((1S,2S,5R,6S)-4-oxo-6-phenyl-3-oxa-bicyclo[3.1.0]hex-2-yl)-propylcarbamoyl]-thiazolidine-3-carboxylic acid tert-butyl ester

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 331821-73-9 [1R,4S,5S,6S,4(1'S)]-[2'-hydroxy-1'-(4-oxo-3-oxa-6-phenylbicyclo[3.1.0]hex-2-yl)ethyl]carbamic acid tert-butyl ester

Send

Send

Metric Ton KG G Pound L ML

Send

Send