(2R,3R,4S)-3-methoxy-4-methyl-5-(phenylmethoxy)pentan-2-ol

Base Information

• Chemical Name: (2R,3R,4S)-3-methoxy-4-methyl-5-(phenylmethoxy)pentan-2-ol
• CAS No.: 329366-69-0
• Molecular Formula: C₁₄H₂₂O₃
• Molecular Weight: 238.327
• Mol file: 329366-69-0.mol

Synonyms:(2R,3R,4S)-3-methoxy-4-methyl-5-(phenylmethoxy)pentan-2-ol

Chemical Property of (2R,3R,4S)-3-methoxy-4-methyl-5-(phenylmethoxy)pentan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S)-3-methoxy-4-methyl-5-(phenylmethoxy)pentan-2-ol

There total 16 articles about (2R,3R,4S)-3-methoxy-4-methyl-5-(phenylmethoxy)pentan-2-ol 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: 92.0%

(R)-2-[(1R,2S)-3-(benzyloxy)-1-methoxy-2-methylpropyl]oxirane (1621332-21-5) → (2R,3R,4S)-3-methoxy-4-methyl-5-(phenylmethoxy)pentan-2-ol (329366-69-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 0.5h; regioselective reaction;

DOI:10.1002/ejoc.201402235

Reference yield: 70.0%

(2R,3S)-2-methoxy-3-methyl-4-(phenylmethoxy)butanal (329366-68-9) + dimethyl zinc(II) (544-97-8) → (2R,3R,4S)-3-methoxy-4-methyl-5-(phenylmethoxy)pentan-2-ol (329366-69-0)

Guidance literature:

(2R,3S)-2-methoxy-3-methyl-4-(phenylmethoxy)butanal; With titanium tetrachloride; In dichloromethane; at -78 ℃; for 0.08h;

dimethyl zinc(II); In tetrahydrofuran; dichloromethane; at -78 ℃; for 0.25h;

With water; In tetrahydrofuran; dichloromethane; at -78 - 18 ℃; stereoselective reaction;

DOI:10.3987/COM-12-12597

Reference yield:

methyl (S)-3-benzyloxy-2-methylpropanoate (74924-27-9) → (2R,3R,4S)-3-methoxy-4-methyl-5-(phenylmethoxy)pentan-2-ol (329366-69-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: isopropylmagnesium chloride / tetrahydrofuran / 1 h / -15 °C / Inert atmosphere

2.1: vinyl magnesium bromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

3.1: zinc borohydride / dichloromethane; diethyl ether / 2.5 h / -78 - 0 °C / Inert atmosphere

4.1: potassium hydride / tetrahydrofuran; mineral oil / 0.25 h / 18 °C / Inert atmosphere

4.2: 0.25 h / 0 - 18 °C / Inert atmosphere

5.1: ozone / dichloromethane / 1 h / -78 °C

5.2: 0.5 h / -30 - 18 °C

6.1: titanium tetrachloride / dichloromethane / 0.08 h / -78 °C

6.2: 0.25 h / -78 °C

6.3: -78 - 18 °C

With zinc borohydride; vinyl magnesium bromide; isopropylmagnesium chloride; titanium tetrachloride; potassium hydride; ozone; In tetrahydrofuran; diethyl ether; dichloromethane; mineral oil;

DOI:10.3987/COM-12-12597

upstream raw materials:

methyl (S)-3-benzyloxy-2-methylpropanoate

O-benzyl 2,2,2-trichloroacetimidate

Weinreb amide of (S)-3-benzyloxy-2-methylpropionic acid

(2S)-1-benzyloxy-2-methyl-4-penten-3-one

Downstream raw materials:

(2R,3R,4S)-3-methoxy-4-methyl-5-(phenylmethoxy)pentan-2-yl (2R)-2-methoxy-2-phenyl-2-trifluoromethylacetate

(2R,3R,4S)-3-methoxy-4-methyl-5-(phenylmethoxy)pentan-2-yl (2S)-2-methoxy-2-phenyl-2-trifluoromethylacetate

[(2R,3R,4S)-5-(benzyloxy)-3-methoxy-4-methylpentan-2-yloxy]-(tert-butyl)dimethylsilane