2,2-dimethyl propionic acid (R)-[(1R,2R)-benzyloxy-1-methyl-tert-butyldimethylsiloxy-butyl]-2-methylallyl ester

Base Information

• Chemical Name: 2,2-dimethyl propionic acid (R)-[(1R,2R)-benzyloxy-1-methyl-tert-butyldimethylsiloxy-butyl]-2-methylallyl ester
• CAS No.: 548488-08-0
• Molecular Formula: C₂₇H₄₆O₄Si
• Molecular Weight: 462.745
• Mol file: 548488-08-0.mol

Synonyms:2,2-dimethyl propionic acid (R)-[(1R,2R)-benzyloxy-1-methyl-tert-butyldimethylsiloxy-butyl]-2-methylallyl ester

Chemical Property of 2,2-dimethyl propionic acid (R)-[(1R,2R)-benzyloxy-1-methyl-tert-butyldimethylsiloxy-butyl]-2-methylallyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-dimethyl propionic acid (R)-[(1R,2R)-benzyloxy-1-methyl-tert-butyldimethylsiloxy-butyl]-2-methylallyl ester

There total 9 articles about 2,2-dimethyl propionic acid (R)-[(1R,2R)-benzyloxy-1-methyl-tert-butyldimethylsiloxy-butyl]-2-methylallyl 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: 97.0%

t-butyldimethylsiyl triflate (69739-34-0) + 2,2-dimethyl propionic acid (R)-[(1R,2R)-1-benzyloxy-1-methyl-2-hydroxybutyl]-2-methylallyl ester (548488-07-9) → 2,2-dimethyl propionic acid (R)-[(1R,2R)-benzyloxy-1-methyl-tert-butyldimethylsiloxy-butyl]-2-methylallyl ester (548488-08-0)

Guidance literature:

With 2,6-dimethylpyridine; at 0 - 23 ℃; for 3h;

DOI:10.1021/ja034865z

Reference yield:

(2R,3R,4R,5R)-4-dimethylphenylsilyl-3-hydroxy-2-hydroxymethyl-2,4-dimethyl-5-ethyltetrahydrofuran (548488-22-8) → 2,2-dimethyl propionic acid (R)-[(1R,2R)-benzyloxy-1-methyl-tert-butyldimethylsiloxy-butyl]-2-methylallyl ester (548488-08-0)

Guidance literature:

Multi-step reaction with 8 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

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

DOI:10.1021/ja034865z

Reference yield:

(2S,3R,4R,5R)-3-acetoxy-4-dimethylphenylsilyl-2,4-dimethyl-5-ethyltetrahydrofuran-2-carboxylic acid ethyl ester (548488-21-7) → 2,2-dimethyl propionic acid (R)-[(1R,2R)-benzyloxy-1-methyl-tert-butyldimethylsiloxy-butyl]-2-methylallyl ester (548488-08-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: LiAlH₄ / diethyl ether / 23 °C

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

2.2: 96 percent / n-Bu₄NI / dimethylformamide / 12 h / 23 °C

3.1: 85 percent / KH; cumene hydroperoxide; NMP / n-Bu₄NF / tetrahydrofuran / 15 h / 60 °C

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

4.2: 95 percent / n-Bu₄NI / dimethylformamide / 12 h / 23 °C

5.1: 96 percent / NaHCO₃; aq. ceric ammonium nitrate; NaHSO₃ / acetonitrile / 1 h / 23 °C

6.1: 78 percent / Ph₃P; imidazole; I₂ / benzene / 1 h / Heating

7.1: 100 percent / Sc(OTf)3 / acetonitrile / 1 h / 23 °C

8.1: 83 percent / Zn; AcOH / methanol; diethyl ether / 12 h / 23 °C

9.1: 97 percent / 2,6-lutidine / 3 h / 0 - 23 °C

With 1H-imidazole; 2,6-dimethylpyridine; 1-methyl-pyrrolidin-2-one; lithium aluminium tetrahydride; ammonium cerium(IV) nitrate; Cumene hydroperoxide; iodine; potassium hydride; sodium hydride; sodium hydrogencarbonate; sodium hydrogensulfite; acetic acid; triphenylphosphine; scandium tris(trifluoromethanesulfonate); zinc; tetrabutyl ammonium fluoride; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/ja034865z

upstream raw materials:

t-butyldimethylsiyl triflate

2,2-dimethyl propionic acid (R)-[(1R,2R)-1-benzyloxy-1-methyl-2-hydroxybutyl]-2-methylallyl ester

(2R,3R,4R,5R)-4-benzyloxy-2,4-dimethyl-5-ethyl-3-hydroxy-2-hydroxymethyltetrahydrofuran

(2R,3R,4R,5R)-4-benzyloxy-2,4-dimethyl-5-ethyl-3-hydroxy-2-iodomethyltetrahydrofuran

Downstream raw materials:

(3R,4S,5R)-4-benzyloxy-2,4-dimethyl-5-(tert-butyldimethylsiloxy)hept-1-en-3-ol

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

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