(1R,2R)-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}-propane-1,3-diol

Base Information

• Chemical Name: (1R,2R)-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}-propane-1,3-diol
• CAS No.: 225928-47-2
• Molecular Formula: C₃₁H₄₄O₇
• Molecular Weight: 528.686
• Mol file: 225928-47-2.mol

Synonyms:

Chemical Property of (1R,2R)-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}-propane-1,3-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R)-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}-propane-1,3-diol

There total 16 articles about (1R,2R)-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}-propane-1,3-diol 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) → (1R,2R)-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}-propane-1,3-diol (225928-47-2)

Guidance literature:

Multi-step reaction with 12 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

With 1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; sodium tetrahydroborate; sodium periodate; lithium borohydride; Schwartz's reagent; n-butyllithium; oxalyl dichloride; N,N-dimethyl-ethanamine; buffer pH 7; dicyclohexylboron chloride; tetrabutyl ammonium fluoride; hydrogen; iodine; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; 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) → (1R,2R)-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}-propane-1,3-diol (225928-47-2)

Guidance literature:

Multi-step reaction with 11 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

With 1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; sodium tetrahydroborate; sodium periodate; lithium borohydride; Schwartz's reagent; n-butyllithium; oxalyl dichloride; N,N-dimethyl-ethanamine; buffer pH 7; dicyclohexylboron chloride; tetrabutyl ammonium fluoride; hydrogen; iodine; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; 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:

(2S,3S)-3-Hydroxy-2-(4-methoxy-benzyloxy)-3-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propionaldehyde → (1R,2R)-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}-propane-1,3-diol (225928-47-2)

Guidance literature:

With sodium tetrahydroborate; In ethanol; Yield given;

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

upstream raw materials:

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

Benzoic acid (R)-3-(4-methoxy-benzyloxy)-1-methyl-2-oxo-propyl ester

Downstream raw materials:

((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

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

2,2-Dimethyl-propionic acid (2R,3R)-3-hydroxy-2-(4-methoxy-benzyloxy)-3-{(4S,5S)-5-[(E)-(S)-7-(4-methoxy-phenyl)-1-methyl-hept-6-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propyl ester