(2R,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-3-phenyl-propionic acid (Z)-(2S,9R,11S)-2-acetoxy-9-(tert-butyl-dimethyl-silanyloxy)-12-methyl-bicyclo[7.3.1]trideca-1⁽¹²⁾,5-diene-3,7-diyn-11-yl ester

Base Information

• Chemical Name: (2R,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-3-phenyl-propionic acid (Z)-(2S,9R,11S)-2-acetoxy-9-(tert-butyl-dimethyl-silanyloxy)-12-methyl-bicyclo[7.3.1]trideca-1⁽¹²⁾,5-diene-3,7-diyn-11-yl ester
• CAS No.: 213924-94-8
• Molecular Formula: C₃₆H₄₇NO₈Si
• Molecular Weight: 649.857

Synonyms:(2R,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-3-phenyl-propionic acid (Z)-(2S,9R,11S)-2-acetoxy-9-(tert-butyl-dimethyl-silanyloxy)-12-methyl-bicyclo[7.3.1]trideca-1⁽¹²⁾,5-diene-3,7-diyn-11-yl ester

Chemical Property of (2R,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-3-phenyl-propionic acid (Z)-(2S,9R,11S)-2-acetoxy-9-(tert-butyl-dimethyl-silanyloxy)-12-methyl-bicyclo[7.3.1]trideca-1⁽¹²⁾,5-diene-3,7-diyn-11-yl ester

Chemical Property:

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Technology Process of (2R,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-3-phenyl-propionic acid (Z)-(2S,9R,11S)-2-acetoxy-9-(tert-butyl-dimethyl-silanyloxy)-12-methyl-bicyclo[7.3.1]trideca-1⁽¹²⁾,5-diene-3,7-diyn-11-yl ester

There total 16 articles about (2R,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-3-phenyl-propionic acid (Z)-(2S,9R,11S)-2-acetoxy-9-(tert-butyl-dimethyl-silanyloxy)-12-methyl-bicyclo[7.3.1]trideca-1⁽¹²⁾,5-diene-3,7-diyn-11-yl 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:

cyclohexanedione monoethylene ketal (4746-97-8) → (2R,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-3-phenyl-propionic acid (Z)-(2S,9R,11S)-2-acetoxy-9-(tert-butyl-dimethyl-silanyloxy)-12-methyl-bicyclo[7.3.1]trideca-1(12),5-diene-3,7-diyn-11-yl ester (213924-94-8)

Guidance literature:

Multi-step reaction with 16 steps

1: 60 percent / LDA, HMPA / tetrahydrofuran / 0.5 h / -78 °C

2: 99 percent / KHMDS / tetrahydrofuran / 1 h / -78 - 21 °C

3: 99 percent / diethyl ether / -78 - 21 °C

4: 80 percent / 35percent aq. CF₃COOH / CHCl₃ / 72 h / 21 °C

5: 84 percent / t-BuLi, CeCl₃ / tetrahydrofuran / 0.17 h / -78 °C

6: 98 percent / Et₃N / CH₂Cl₂ / 0 - 21 °C

7: 99 percent / i-Bu₂AlH / CH₂Cl₂ / 2 h / -78 - -60 °C

8: 93 percent / n-Bu₄NF / tetrahydrofuran / 4 h / -78 - 0 °C

9: 69 percent / I₂, morpholine / benzene / 2 h / 60 °C

10: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 21 °C

11: 76 percent / 2*(THF)2> / tetrahydrofuran / 0.5 h

12: 99 percent / DMAP / pyridine / 15 h / 21 °C

13: 66 percent / SeO₂ / dioxane / 0.5 h / 70 °C

14: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.75 h / 21 °C

15: 41 percent / NaBH₄, CeCl₃ / methanol / 0 °C

16: 1.) DCC, DMAP, 2.) PTSA / 1.) toluene, 21 deg C, 30 min, 2.) MeOH, 21 deg C, 1.5 h

With morpholine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; selenium(IV) oxide; cerium(III) chloride; CrCl₂(tetrahydrofuran)2; tetrabutyl ammonium fluoride; iodine; tert.-butyl lithium; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; diethyl ether; dichloromethane; chloroform; benzene;

DOI:10.1016/S0040-4039(98)01297-0

Reference yield:

ethyl 8-oxo-1,4-dioxaspiro[4.5]decane-7-carboxylate (14160-65-7,77793-24-9,122090-88-4) → (2R,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-3-phenyl-propionic acid (Z)-(2S,9R,11S)-2-acetoxy-9-(tert-butyl-dimethyl-silanyloxy)-12-methyl-bicyclo[7.3.1]trideca-1(12),5-diene-3,7-diyn-11-yl ester (213924-94-8)

Guidance literature:

Multi-step reaction with 15 steps

1: 99 percent / KHMDS / tetrahydrofuran / 1 h / -78 - 21 °C

2: 99 percent / diethyl ether / -78 - 21 °C

3: 80 percent / 35percent aq. CF₃COOH / CHCl₃ / 72 h / 21 °C

4: 84 percent / t-BuLi, CeCl₃ / tetrahydrofuran / 0.17 h / -78 °C

5: 98 percent / Et₃N / CH₂Cl₂ / 0 - 21 °C

6: 99 percent / i-Bu₂AlH / CH₂Cl₂ / 2 h / -78 - -60 °C

7: 93 percent / n-Bu₄NF / tetrahydrofuran / 4 h / -78 - 0 °C

8: 69 percent / I₂, morpholine / benzene / 2 h / 60 °C

9: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 21 °C

10: 76 percent / 2*(THF)2> / tetrahydrofuran / 0.5 h

11: 99 percent / DMAP / pyridine / 15 h / 21 °C

12: 66 percent / SeO₂ / dioxane / 0.5 h / 70 °C

13: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.75 h / 21 °C

14: 41 percent / NaBH₄, CeCl₃ / methanol / 0 °C

15: 1.) DCC, DMAP, 2.) PTSA / 1.) toluene, 21 deg C, 30 min, 2.) MeOH, 21 deg C, 1.5 h

With morpholine; dmap; sodium tetrahydroborate; selenium(IV) oxide; cerium(III) chloride; CrCl₂(tetrahydrofuran)2; tetrabutyl ammonium fluoride; iodine; tert.-butyl lithium; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; diethyl ether; dichloromethane; chloroform; benzene;

DOI:10.1016/S0040-4039(98)01297-0

Reference yield:

2-Methyl-5-oxo-cyclohex-1-enecarboxylic acid ethyl ester (98046-49-2) → (2R,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-3-phenyl-propionic acid (Z)-(2S,9R,11S)-2-acetoxy-9-(tert-butyl-dimethyl-silanyloxy)-12-methyl-bicyclo[7.3.1]trideca-1(12),5-diene-3,7-diyn-11-yl ester (213924-94-8)

Guidance literature:

Multi-step reaction with 12 steps

1: 84 percent / t-BuLi, CeCl₃ / tetrahydrofuran / 0.17 h / -78 °C

2: 98 percent / Et₃N / CH₂Cl₂ / 0 - 21 °C

3: 99 percent / i-Bu₂AlH / CH₂Cl₂ / 2 h / -78 - -60 °C

4: 93 percent / n-Bu₄NF / tetrahydrofuran / 4 h / -78 - 0 °C

5: 69 percent / I₂, morpholine / benzene / 2 h / 60 °C

6: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 21 °C

7: 76 percent / 2*(THF)2> / tetrahydrofuran / 0.5 h

8: 99 percent / DMAP / pyridine / 15 h / 21 °C

9: 66 percent / SeO₂ / dioxane / 0.5 h / 70 °C

10: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.75 h / 21 °C

11: 41 percent / NaBH₄, CeCl₃ / methanol / 0 °C

12: 1.) DCC, DMAP, 2.) PTSA / 1.) toluene, 21 deg C, 30 min, 2.) MeOH, 21 deg C, 1.5 h

With morpholine; dmap; sodium tetrahydroborate; selenium(IV) oxide; cerium(III) chloride; CrCl₂(tetrahydrofuran)2; tetrabutyl ammonium fluoride; iodine; tert.-butyl lithium; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; dichloromethane; benzene;

DOI:10.1016/S0040-4039(98)01297-0

upstream raw materials:

(2R,4S,5R)-(2R,4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid

cyclohexanedione monoethylene ketal

ethyl 8-oxo-1,4-dioxaspiro[4.5]decane-7-carboxylate

2-Methyl-5-oxo-cyclohex-1-enecarboxylic acid ethyl ester

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