(2R,4R,5S)-4-[(1S,2R)-1-benzyloxy-2-tert-butyldimethylsiloxy-1-methylbutyl]-2-(p-methoxyphenyl)-5-methyl-1,3-dioxane

Base Information

• Chemical Name: (2R,4R,5S)-4-[(1S,2R)-1-benzyloxy-2-tert-butyldimethylsiloxy-1-methylbutyl]-2-(p-methoxyphenyl)-5-methyl-1,3-dioxane
• CAS No.: 548488-09-1
• Molecular Formula: C₃₀H₄₆O₅Si
• Molecular Weight: 514.778
• Mol file: 548488-09-1.mol

Synonyms:(2R,4R,5S)-4-[(1S,2R)-1-benzyloxy-2-tert-butyldimethylsiloxy-1-methylbutyl]-2-(p-methoxyphenyl)-5-methyl-1,3-dioxane

Chemical Property of (2R,4R,5S)-4-[(1S,2R)-1-benzyloxy-2-tert-butyldimethylsiloxy-1-methylbutyl]-2-(p-methoxyphenyl)-5-methyl-1,3-dioxane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4R,5S)-4-[(1S,2R)-1-benzyloxy-2-tert-butyldimethylsiloxy-1-methylbutyl]-2-(p-methoxyphenyl)-5-methyl-1,3-dioxane

There total 17 articles about (2R,4R,5S)-4-[(1S,2R)-1-benzyloxy-2-tert-butyldimethylsiloxy-1-methylbutyl]-2-(p-methoxyphenyl)-5-methyl-1,3-dioxane 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: 96.0%

p-Anisaldehyde dimethyl acetal (2186-92-7) + (2S,3R,4S,5R)-4-benzyloxy-2,4-dimethyl-5-(tert-butyldimethylsiloxy)heptane-1,3-diol (548487-87-2) → (2R,4R,5S)-4-[(1S,2R)-1-benzyloxy-2-tert-butyldimethylsiloxy-1-methylbutyl]-2-(p-methoxyphenyl)-5-methyl-1,3-dioxane (548488-09-1)

Guidance literature:

With p-Anisaldehyde dimethyl acetal; pyridinium p-toluenesulfonate; In dichloromethane; at 23 ℃; for 5h;

DOI:10.1021/ja034865z

Reference yield: 76.0%

3-(tert-butyl-dimethyl-silanyloxy)-2-[2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-pentan-2-ol (933487-16-2) + benzyl bromide (100-39-0) → (2R,4R,5S)-4-[(1S,2R)-1-benzyloxy-2-tert-butyldimethylsiloxy-1-methylbutyl]-2-(p-methoxyphenyl)-5-methyl-1,3-dioxane (548488-09-1)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 4h;

DOI:10.1021/ja068813w

Reference yield:

(2R,3R,4R,5R)-4-dimethylphenylsilyl-3-hydroxy-2-hydroxymethyl-2,4-dimethyl-5-ethyltetrahydrofuran (548488-22-8) → (2R,4R,5S)-4-[(1S,2R)-1-benzyloxy-2-tert-butyldimethylsiloxy-1-methylbutyl]-2-(p-methoxyphenyl)-5-methyl-1,3-dioxane (548488-09-1)

Guidance literature:

Multi-step reaction with 11 steps

1.1: NaH / dimethylformamide / 0.5 h / 23 °C

1.2: 96 percent / n-Bu₄NI / dimethylformamide / 12 h / 23 °C

2.1: 85 percent / KH; cumene hydroperoxide; NMP / n-Bu₄NF / tetrahydrofuran / 15 h / 60 °C

3.1: NaH / dimethylformamide / 0.5 h / 0 °C

3.2: 95 percent / n-Bu₄NI / dimethylformamide / 12 h / 23 °C

4.1: 96 percent / NaHCO₃; aq. ceric ammonium nitrate; NaHSO₃ / acetonitrile / 1 h / 23 °C

5.1: 78 percent / Ph₃P; imidazole; I₂ / benzene / 1 h / Heating

6.1: 100 percent / Sc(OTf)3 / acetonitrile / 1 h / 23 °C

7.1: 83 percent / Zn; AcOH / methanol; diethyl ether / 12 h / 23 °C

8.1: 97 percent / 2,6-lutidine / 3 h / 0 - 23 °C

9.1: 94 percent / i-Bu₂AlH / CH₂Cl₂; toluene / -78 - 0 °C

10.1: HN(SiHMe₂) / 24 h / 90 °C

10.2: 87 percent / Pt⁽⁰⁾-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex / toluene; xylene / 12 h / 70 °C

11.1: 96 percent / p-anisaldehyde dimethylacetal; PPTS / CH₂Cl₂ / 5 h / 23 °C

With 1H-imidazole; 2,6-dimethylpyridine; 1-methyl-pyrrolidin-2-one; ammonium cerium(IV) nitrate; Cumene hydroperoxide; p-Anisaldehyde dimethyl acetal; iodine; pyridinium p-toluenesulfonate; potassium hydride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; sodium hydrogensulfite; acetic acid; triphenylphosphine; 1,1,3,3-tetramethyldisilazane; scandium tris(trifluoromethanesulfonate); zinc; tetrabutyl ammonium fluoride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;

DOI:10.1021/ja034865z

upstream raw materials:

p-Anisaldehyde dimethyl acetal

(2S,3R,4S,5R)-4-benzyloxy-2,4-dimethyl-5-(tert-butyldimethylsiloxy)heptane-1,3-diol

3-(tert-butyl-dimethyl-silanyloxy)-2-[2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-pentan-2-ol

benzyl bromide