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

Base Information

• Chemical Name: (2R,3R,4R,5R)-4-benzyloxy-2,4-dimethyl-5-ethyl-3-hydroxy-2-iodomethyltetrahydrofuran
• CAS No.: 548488-06-8
• Molecular Formula: C₁₆H₂₃IO₃
• Molecular Weight: 390.261
• Mol file: 548488-06-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about (2R,3R,4R,5R)-4-benzyloxy-2,4-dimethyl-5-ethyl-3-hydroxy-2-iodomethyltetrahydrofuran 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: 78.0%

(2R,3R,4R,5R)-4-benzyloxy-2,4-dimethyl-5-ethyl-3-hydroxy-2-hydroxymethyltetrahydrofuran (98004-04-7) → (2R,3R,4R,5R)-4-benzyloxy-2,4-dimethyl-5-ethyl-3-hydroxy-2-iodomethyltetrahydrofuran (548488-06-8)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In benzene; for 1h; Heating;

DOI:10.1021/ja034865z

Reference yield:

(2R,3R,4R,5R)-4-dimethylphenylsilyl-3-hydroxy-2-hydroxymethyl-2,4-dimethyl-5-ethyltetrahydrofuran (548488-22-8) → (2R,3R,4R,5R)-4-benzyloxy-2,4-dimethyl-5-ethyl-3-hydroxy-2-iodomethyltetrahydrofuran (548488-06-8)

Guidance literature:

Multi-step reaction with 5 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

With 1H-imidazole; 1-methyl-pyrrolidin-2-one; ammonium cerium(IV) nitrate; Cumene hydroperoxide; iodine; potassium hydride; sodium hydride; sodium hydrogencarbonate; sodium hydrogensulfite; triphenylphosphine; tetrabutyl ammonium fluoride; In tetrahydrofuran; 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) → (2R,3R,4R,5R)-4-benzyloxy-2,4-dimethyl-5-ethyl-3-hydroxy-2-iodomethyltetrahydrofuran (548488-06-8)

Guidance literature:

Multi-step reaction with 6 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

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

DOI:10.1021/ja034865z

upstream raw materials:

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

(2R,3R,4R,5R)-4-dimethylphenylsilyl-3-hydroxy-2-hydroxymethyl-2,4-dimethyl-5-ethyltetrahydrofuran

(2S,3R,4R,5R)-3-acetoxy-4-dimethylphenylsilyl-2,4-dimethyl-5-ethyltetrahydrofuran-2-carboxylic acid ethyl ester

(2R,3R,4R,5R)-2,4-dimethyl-5-ethyl-4-hydroxy-3-(p-methoxybenzyloxy)-2-(p-methoxybenzyloxymethyl)tetrahydrofuran

Downstream raw materials:

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

(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

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