Carpetimycin A

Base Information

• Chemical Name: Carpetimycin A
• CAS No.: 76025-73-5
• Molecular Formula: C₁₄H₁₈N₂O₆S
• Molecular Weight: 342.373
• UNII: 2LV1X0V38M
• Wikidata: Q27254906
• Mol file: 76025-73-5.mol

Synonyms:C 19393 H(2);C-19393 H(2);carpetimycin A

Chemical Property of Carpetimycin A

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: >145° (dec)
• Boiling Point: 691.786°C at 760 mmHg
• Flash Point: 372.179°C
• PSA: 146.71000
• Density: 1.554g/cm³
• LogP: 1.28410
• XLogP3: -1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 342.08855747
• Heavy Atom Count: 23
• Complexity: 666

Purity/Quality:

95% ^*data from raw suppliers

CARPETIMYCIN A 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC=CS(=O)C1=C(N2C(C1)C(C2=O)C(C)(C)O)C(=O)O
• Isomeric SMILES: CC(=O)N/C=C/[S@@](=O)C1=C(N2[C@H](C1)[C@@H](C2=O)C(C)(C)O)C(=O)O

Technology Process of Carpetimycin A

There total 16 articles about Carpetimycin A 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:

(5R,6R)-3-((R)-(E)-2-Acetylamino-ethenesulfinyl)-6-(1-hydroxy-1-methyl-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (79244-00-1) → carpetimycin A (76025-73-5)

Guidance literature:

With phosphate buffer; hydrogen; palladium on activated charcoal; In 1,4-dioxane;

DOI:10.1021/ja00344a044

Reference yield:

(S)-3-<(benzyloxycarbonyl)amino>-4-(methoxycarbonyl)butyric acid (77856-52-1) → carpetimycin A (76025-73-5)

Guidance literature:

Multi-step reaction with 16 steps

1: NaBH₄

2: Ac₂O / pyridine

3: 77 percent / LDA / tetrahydrofuran / 1 h / -78 °C

4: 88 percent Turnov_. / hydrochloric acid

5: H₂, catalyst

6: Et₃N / diethyl ether / 2 h / 25 °C

7: t-BuMgCl / diethyl ether / 12 h / 25 °C

8: 1percent AcOH / methanol / 24 h / 25 °C

9: 66 percent / CrO₃ / pyridine / 12 h / 25 °C

10: 1.) carbonyl diimidazole / 1.) THF, 25 deg C, 45 min, 2.) TFH, 25 deg C, 12 h

11: TsN₃, Et₃N / acetonitrile / 12 h / 25 °C

12: 1N HCl / methanol / 0.67 h / 25 °C

13: Rh₂(OAc)4 / benzene / 1 h / Heating

15: 45 percent / MPCBA / CH₂Cl₂ / -30 deg C -> -5 deg C, 70 min

16: H₂, phosphate buffer, pH 6.8 / 10percent Pd/C / dioxane

With chromium(VI) oxide; hydrogenchloride; dirhodium tetraacetate; sodium tetrahydroborate; 4-toluenesulfonyl azide; phosphate buffer; tert-butylmagnesium chloride; hydrogen; acetic anhydride; acetic acid; triethylamine; 1,1'-carbonyldiimidazole; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; diethyl ether; dichloromethane; acetonitrile; benzene;

DOI:10.1021/ja00344a044

Reference yield:

(2R,3R)-3-Amino-5-hydroxy-2-(1-hydroxy-1-methyl-ethyl)-pentanoic acid methyl ester (84787-58-6) → carpetimycin A (76025-73-5)

Guidance literature:

Multi-step reaction with 11 steps

1: Et₃N / diethyl ether / 2 h / 25 °C

2: t-BuMgCl / diethyl ether / 12 h / 25 °C

3: 1percent AcOH / methanol / 24 h / 25 °C

4: 66 percent / CrO₃ / pyridine / 12 h / 25 °C

5: 1.) carbonyl diimidazole / 1.) THF, 25 deg C, 45 min, 2.) TFH, 25 deg C, 12 h

6: TsN₃, Et₃N / acetonitrile / 12 h / 25 °C

7: 1N HCl / methanol / 0.67 h / 25 °C

8: Rh₂(OAc)4 / benzene / 1 h / Heating

10: 45 percent / MPCBA / CH₂Cl₂ / -30 deg C -> -5 deg C, 70 min

11: H₂, phosphate buffer, pH 6.8 / 10percent Pd/C / dioxane

With chromium(VI) oxide; hydrogenchloride; dirhodium tetraacetate; 4-toluenesulfonyl azide; phosphate buffer; tert-butylmagnesium chloride; hydrogen; acetic acid; triethylamine; 1,1'-carbonyldiimidazole; palladium on activated charcoal; In 1,4-dioxane; pyridine; methanol; diethyl ether; dichloromethane; acetonitrile; benzene;

DOI:10.1021/ja00344a044

upstream raw materials:

(5R,6R)-3-((R)-(E)-2-Acetylamino-ethenesulfinyl)-6-(1-hydroxy-1-methyl-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(S)-3-<(benzyloxycarbonyl)amino>-4-(methoxycarbonyl)butyric acid

(2R,3R)-3-Amino-5-hydroxy-2-(1-hydroxy-1-methyl-ethyl)-pentanoic acid methyl ester

(3R,4R)-4-(2-Hydroxy-ethyl)-3-(1-methyl-1-trimethylsilanyloxy-ethyl)-azetidin-2-one