((1S,2S)-3-Hydroxy-2-(4-methoxy-benzyloxy)-1-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propyl)-carbamic acid tert-butyl ester

Base Information

• Chemical Name: ((1S,2S)-3-Hydroxy-2-(4-methoxy-benzyloxy)-1-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propyl)-carbamic acid tert-butyl ester
• CAS No.: 225928-49-4
• Molecular Formula: C₃₆H₅₃NO₈
• Molecular Weight: 627.819

Synonyms:

Chemical Property of ((1S,2S)-3-Hydroxy-2-(4-methoxy-benzyloxy)-1-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propyl)-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((1S,2S)-3-Hydroxy-2-(4-methoxy-benzyloxy)-1-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propyl)-carbamic acid tert-butyl ester

There total 20 articles about ((1S,2S)-3-Hydroxy-2-(4-methoxy-benzyloxy)-1-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propyl)-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:

[(4S,5S)-5-((S)-5-Benzyloxy-1-methyl-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol (190712-24-4) → ((1S,2S)-3-Hydroxy-2-(4-methoxy-benzyloxy)-1-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propyl)-carbamic acid tert-butyl ester (225928-49-4)

Guidance literature:

Multi-step reaction with 17 steps

1: 97 percent / imidazole / dimethylformamide

2: 99 percent / H₂ / 5 percent Pd/C / ethyl acetate

3: I₂, imidazole, Ph₃P / benzene

4: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide

5: K₂CO₃ / methanol

6: 1.) Cp₂Zr(H)Cl; 2.) (Ph₃P)2PdCl₂, DIBAL / 1.) THF; 2.) THF

7: TBAF / tetrahydrofuran

8: (COCl)2, Et₃N, DMSO / CH₂Cl₂

9: (cyclohexyl)2BCl, Me₂NEt / diethyl ether

10: 79 percent / LiBH₄ / tetrahydrofuran

11: NaIO₄, buffer pH 7 / tetrahydrofuran

12: NaBH₄ / ethanol

13: 83 percent / pyridine

14: pyridine / CH₂Cl₂

15: n-Bu₄NN₃ / benzene

16: LiAlH₄ / tetrahydrofuran

17: dioxane

With pyridine; 1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; lithium borohydride; Schwartz's reagent; n-butyllithium; oxalyl dichloride; N,N-dimethyl-ethanamine; buffer pH 7; dicyclohexylboron chloride; tetrabutyl ammonium fluoride; hydrogen; iodine; tetrabutylammoniun azide; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4039(99)00411-6

Reference yield:

[(4S,5S)-5-((S)-5-Benzyloxy-1-methyl-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-tert-butyl-dimethyl-silane (225928-52-9) → ((1S,2S)-3-Hydroxy-2-(4-methoxy-benzyloxy)-1-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propyl)-carbamic acid tert-butyl ester (225928-49-4)

Guidance literature:

Multi-step reaction with 16 steps

1: 99 percent / H₂ / 5 percent Pd/C / ethyl acetate

2: I₂, imidazole, Ph₃P / benzene

3: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide

4: K₂CO₃ / methanol

5: 1.) Cp₂Zr(H)Cl; 2.) (Ph₃P)2PdCl₂, DIBAL / 1.) THF; 2.) THF

6: TBAF / tetrahydrofuran

7: (COCl)2, Et₃N, DMSO / CH₂Cl₂

8: (cyclohexyl)2BCl, Me₂NEt / diethyl ether

9: 79 percent / LiBH₄ / tetrahydrofuran

10: NaIO₄, buffer pH 7 / tetrahydrofuran

11: NaBH₄ / ethanol

12: 83 percent / pyridine

13: pyridine / CH₂Cl₂

14: n-Bu₄NN₃ / benzene

15: LiAlH₄ / tetrahydrofuran

16: dioxane

With pyridine; 1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; lithium borohydride; Schwartz's reagent; n-butyllithium; oxalyl dichloride; N,N-dimethyl-ethanamine; buffer pH 7; dicyclohexylboron chloride; tetrabutyl ammonium fluoride; hydrogen; iodine; tetrabutylammoniun azide; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; dichloromethane; ethyl acetate; benzene;

DOI:10.1016/S0040-4039(99)00411-6

Reference yield:

para-iodoanisole (696-62-8) → ((1S,2S)-3-Hydroxy-2-(4-methoxy-benzyloxy)-1-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propyl)-carbamic acid tert-butyl ester (225928-49-4)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) Cp₂Zr(H)Cl; 2.) (Ph₃P)2PdCl₂, DIBAL / 1.) THF; 2.) THF

2: TBAF / tetrahydrofuran

3: (COCl)2, Et₃N, DMSO / CH₂Cl₂

4: (cyclohexyl)2BCl, Me₂NEt / diethyl ether

5: 79 percent / LiBH₄ / tetrahydrofuran

6: NaIO₄, buffer pH 7 / tetrahydrofuran

7: NaBH₄ / ethanol

8: 83 percent / pyridine

9: pyridine / CH₂Cl₂

10: n-Bu₄NN₃ / benzene

11: LiAlH₄ / tetrahydrofuran

12: dioxane

With pyridine; bis-triphenylphosphine-palladium(II) chloride; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; lithium borohydride; Schwartz's reagent; oxalyl dichloride; N,N-dimethyl-ethanamine; buffer pH 7; dicyclohexylboron chloride; tetrabutyl ammonium fluoride; tetrabutylammoniun azide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; dichloromethane; benzene;

DOI:10.1016/S0040-4039(99)00411-6

upstream raw materials:

di-tert-butyl dicarbonate

para-iodoanisole

[(4S,5S)-5-((S)-5-Benzyloxy-1-methyl-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol

(R)-3-Hydroxy-1-(4-methoxy-benzyloxy)-butan-2-one

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