{3-[(S)-1-((R)-1-Benzyloxy-2-hydroxy-ethyl)-6-(tert-butyl-diphenyl-silanyloxy)-1,5-dimethyl-hexyloxy]-2-oxo-propyl}-phosphonic acid dimethyl ester

Base Information

• Chemical Name: {3-[(S)-1-((R)-1-Benzyloxy-2-hydroxy-ethyl)-6-(tert-butyl-diphenyl-silanyloxy)-1,5-dimethyl-hexyloxy]-2-oxo-propyl}-phosphonic acid dimethyl ester
• CAS No.: 849411-97-8
• Molecular Formula: C₃₈H₅₅O₈PSi
• Molecular Weight: 698.909
• Mol file: 849411-97-8.mol

Synonyms:{3-[(S)-1-((R)-1-Benzyloxy-2-hydroxy-ethyl)-6-(tert-butyl-diphenyl-silanyloxy)-1,5-dimethyl-hexyloxy]-2-oxo-propyl}-phosphonic acid dimethyl ester

Chemical Property of {3-[(S)-1-((R)-1-Benzyloxy-2-hydroxy-ethyl)-6-(tert-butyl-diphenyl-silanyloxy)-1,5-dimethyl-hexyloxy]-2-oxo-propyl}-phosphonic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {3-[(S)-1-((R)-1-Benzyloxy-2-hydroxy-ethyl)-6-(tert-butyl-diphenyl-silanyloxy)-1,5-dimethyl-hexyloxy]-2-oxo-propyl}-phosphonic acid dimethyl ester

There total 11 articles about {3-[(S)-1-((R)-1-Benzyloxy-2-hydroxy-ethyl)-6-(tert-butyl-diphenyl-silanyloxy)-1,5-dimethyl-hexyloxy]-2-oxo-propyl}-phosphonic acid dimethyl 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: 84.0%

dimethyl 3-{(1S)-1-[(1S)-1-benzyloxy-2-methoxymethoxyethyl]-6-(tert-butyldiphenylsilanyloxy)-1,5-dimethylhexyloxy}-2-oxopropylphosphonate (724422-95-1) → {3-[(S)-1-((R)-1-Benzyloxy-2-hydroxy-ethyl)-6-(tert-butyl-diphenyl-silanyloxy)-1,5-dimethyl-hexyloxy]-2-oxo-propyl}-phosphonic acid dimethyl ester (849411-97-8)

Guidance literature:

With trimethylsilyl bromide; In dichloromethane; at -40 ℃;

DOI:10.1021/ol049433n

Reference yield:

(+-)-2-methyl-pent-4-enoic acid (1575-74-2) → {3-[(S)-1-((R)-1-Benzyloxy-2-hydroxy-ethyl)-6-(tert-butyl-diphenyl-silanyloxy)-1,5-dimethyl-hexyloxy]-2-oxo-propyl}-phosphonic acid dimethyl ester (849411-97-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: LiAlH₄ / tetrahydrofuran / 16 h / 20 °C

2.1: 91 percent / imidazole / dimethylformamide / 12 h / 20 °C

3.1: 9-BBN dimer / tetrahydrofuran / 2 h / 0 °C

3.2: 74 percent / K₃PO₄ / Pd(PPh₃)4 / tetrahydrofuran; dioxane / 5 h / 85 °C

4.1: AD-mix-β; MeSO2NH2 / H2O; 2-methyl-propan-2-ol; toluene / 30 h / 0 °C

5.1: 74 percent / n-Bu₄NI; Ag₂O / CH₂Cl₂ / 5 h / 20 °C

6.1: LiAlH₄ / diethyl ether / 0 - 20 °C

7.1: 0.445 g / NaH / tetrahydrofuran / 3 h / 0 - 20 °C

8.1: [Rh(OAc)2]2 / toluene / 2 h / 110 °C

9.1: 118 mg / n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

10.1: 84 percent / Me₃SiBr / CH₂Cl₂ / 0.5 h / -40 °C

With 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; trimethylsilyl bromide; methanesulfonamide; AD-mix-β; tetra-(n-butyl)ammonium iodide; sodium hydride; silver(l) oxide; dimeric 9-borabicyclo[3.3.1]nonane; dirhodium tetraacetate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 3.2: Suzuki-Miyaura coupling / 4.1: Sharpless dihydroxylation;

DOI:10.1021/jo048115z

Reference yield:

2-methylpent-4-en-1-ol (5673-98-3) → {3-[(S)-1-((R)-1-Benzyloxy-2-hydroxy-ethyl)-6-(tert-butyl-diphenyl-silanyloxy)-1,5-dimethyl-hexyloxy]-2-oxo-propyl}-phosphonic acid dimethyl ester (849411-97-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 91 percent / imidazole / dimethylformamide / 12 h / 20 °C

2.1: 9-BBN dimer / tetrahydrofuran / 2 h / 0 °C

2.2: 74 percent / K₃PO₄ / Pd(PPh₃)4 / tetrahydrofuran; dioxane / 5 h / 85 °C

3.1: AD-mix-β; MeSO2NH2 / H2O; 2-methyl-propan-2-ol; toluene / 30 h / 0 °C

4.1: 74 percent / n-Bu₄NI; Ag₂O / CH₂Cl₂ / 5 h / 20 °C

5.1: LiAlH₄ / diethyl ether / 0 - 20 °C

6.1: 0.445 g / NaH / tetrahydrofuran / 3 h / 0 - 20 °C

7.1: [Rh(OAc)2]2 / toluene / 2 h / 110 °C

8.1: 118 mg / n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

9.1: 84 percent / Me₃SiBr / CH₂Cl₂ / 0.5 h / -40 °C

With 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; trimethylsilyl bromide; methanesulfonamide; AD-mix-β; tetra-(n-butyl)ammonium iodide; sodium hydride; silver(l) oxide; dimeric 9-borabicyclo[3.3.1]nonane; dirhodium tetraacetate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 2.2: Suzuki-Miyaura coupling / 3.1: Sharpless dihydroxylation;

DOI:10.1021/jo048115z

upstream raw materials:

dimethyl 3-{(1S)-1-[(1S)-1-benzyloxy-2-methoxymethoxyethyl]-6-(tert-butyldiphenylsilanyloxy)-1,5-dimethylhexyloxy}-2-oxopropylphosphonate

(+-)-2-methyl-pent-4-enoic acid

2-methylpent-4-en-1-ol

tert-butyldipheny((2-methylpent-4-en-1-yl)oxy)silane

Downstream raw materials:

5-{(2S,3R)-3-Benzyloxy-6-[2-benzyloxy-eth-(E)-ylidene]-2-methyl-oxepan-2-yl}-2-methyl-pentan-1-ol

5-{(2S,3R)-3-Benzyloxy-6-[2-benzyloxy-eth-(E)-ylidene]-2-methyl-oxepan-2-yl}-2-methyl-pentanoic acid

(E)-5-[3-(2S,3R)-benzyloxy-6-(2-benzyloxyethylidene)-2-methyloxepan-2-yl]-N-methoxy-2,N-dimethylpentanamide

(6R,7S)-6-benzyloxy-7-[5-(tert-butyldiphenylsilanyloxy)-4-methylpentyl]-7-methyl-6,7-dihydrooxepin-3-one