(E)-5-(1-Benzyloxycarbonylmethyl-cyclohexyl)-2-tert-butoxycarbonylamino-pent-4-enoic acid

Base Information

• Chemical Name: (E)-5-(1-Benzyloxycarbonylmethyl-cyclohexyl)-2-tert-butoxycarbonylamino-pent-4-enoic acid
• CAS No.: 138971-84-3
• Molecular Formula: C₂₅H₃₅NO₆
• Molecular Weight: 445.556

Synonyms:(E)-5-(1-Benzyloxycarbonylmethyl-cyclohexyl)-2-tert-butoxycarbonylamino-pent-4-enoic acid

Chemical Property of (E)-5-(1-Benzyloxycarbonylmethyl-cyclohexyl)-2-tert-butoxycarbonylamino-pent-4-enoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-5-(1-Benzyloxycarbonylmethyl-cyclohexyl)-2-tert-butoxycarbonylamino-pent-4-enoic acid

There total 16 articles about (E)-5-(1-Benzyloxycarbonylmethyl-cyclohexyl)-2-tert-butoxycarbonylamino-pent-4-enoic acid 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: 78.0%

(E)-5-(1-Benzyloxycarbonylmethyl-cyclohexyl)-2-tert-butoxycarbonylamino-pent-4-enoic acid ethyl ester (138971-83-2) → (E)-5-(1-Benzyloxycarbonylmethyl-cyclohexyl)-2-tert-butoxycarbonylamino-pent-4-enoic acid (138971-84-3)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; Ambient temperature;

DOI:10.1016/0040-4039(91)80476-M

Reference yield:

1,1,-Cyclohexanediacetic acid monobenzyl ester (113009-25-9) → (E)-5-(1-Benzyloxycarbonylmethyl-cyclohexyl)-2-tert-butoxycarbonylamino-pent-4-enoic acid (138971-84-3)

Guidance literature:

Multi-step reaction with 17 steps

1: (COCl)2 / toluene / Ambient temperature

2: diethyl ether / 0 °C

3: AgOCOPh, Et₃N / Ambient temperature

4: H₂ / Pd/C / methanol

5: 1.) LDA / 1.) THF, -78 deg C to -20 deg C, 2.) -78 deg C

6: NaIO₄ / methanol / 0 °C

7: CaCO₃ / toluene / Heating

8: 1.) 1 N aq. NaOH, 2.) 1 N aq. HCl / 1.) MeOH, room temperature, 2.) room temperature

9: DCC, DMAP / CH₂Cl₂

10: 99 percent / TFA / CH₂Cl₂ / Ambient temperature

11: (COCl)2 / toluene / Ambient temperature

12: NaBH₄ / tetrahydrofuran / 0 °C

13: 1.) CCl₄, n-Bu₃P, 2.) NaI / 1.) 0 deg C to room temperature, 2.) acetone, reflux

14: 1.) LDA / 1.) THF, -78 deg C, 2.) -78 deg C to room temperature

15: 1 N aq. HCl / CH₂Cl₂ / Ambient temperature

16: Et₃N / CH₂Cl₂ / Ambient temperature

17: 78 percent / 1 N aq. NaOH / dioxane / Ambient temperature

With hydrogenchloride; tetrachloromethane; dmap; sodium hydroxide; sodium tetrahydroborate; sodium periodate; oxalyl dichloride; tributylphosphine; hydrogen; silver benzoate; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; calcium carbonate; sodium iodide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; toluene;

DOI:10.1016/0040-4039(91)80476-M

Reference yield:

(1-Chlorocarbonylmethyl-cyclohexyl)-acetic acid benzyl ester → (E)-5-(1-Benzyloxycarbonylmethyl-cyclohexyl)-2-tert-butoxycarbonylamino-pent-4-enoic acid (138971-84-3)

Guidance literature:

Multi-step reaction with 16 steps

1: diethyl ether / 0 °C

2: AgOCOPh, Et₃N / Ambient temperature

3: H₂ / Pd/C / methanol

4: 1.) LDA / 1.) THF, -78 deg C to -20 deg C, 2.) -78 deg C

5: NaIO₄ / methanol / 0 °C

6: CaCO₃ / toluene / Heating

7: 1.) 1 N aq. NaOH, 2.) 1 N aq. HCl / 1.) MeOH, room temperature, 2.) room temperature

8: DCC, DMAP / CH₂Cl₂

9: 99 percent / TFA / CH₂Cl₂ / Ambient temperature

10: (COCl)2 / toluene / Ambient temperature

11: NaBH₄ / tetrahydrofuran / 0 °C

12: 1.) CCl₄, n-Bu₃P, 2.) NaI / 1.) 0 deg C to room temperature, 2.) acetone, reflux

13: 1.) LDA / 1.) THF, -78 deg C, 2.) -78 deg C to room temperature

14: 1 N aq. HCl / CH₂Cl₂ / Ambient temperature

15: Et₃N / CH₂Cl₂ / Ambient temperature

16: 78 percent / 1 N aq. NaOH / dioxane / Ambient temperature

With hydrogenchloride; tetrachloromethane; dmap; sodium hydroxide; sodium tetrahydroborate; sodium periodate; oxalyl dichloride; tributylphosphine; hydrogen; silver benzoate; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; calcium carbonate; sodium iodide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; toluene;

DOI:10.1016/0040-4039(91)80476-M

upstream raw materials:

(E)-5-(1-Benzyloxycarbonylmethyl-cyclohexyl)-2-tert-butoxycarbonylamino-pent-4-enoic acid ethyl ester

(3-Oxo-2-oxa-spiro[4.5]dec-1-yl)-acetic acid tert-butyl ester

3-(1-Carboxymethyl-cyclohexyl)-propionic acid tert-butyl ester

[1-((E)-3-Iodo-propenyl)-cyclohexyl]-acetic acid benzyl ester

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