(2S,3R)-5-benzyloxy-3-methylpentane-<2-2H>-1,3-diol

Base Information

• Chemical Name: (2S,3R)-5-benzyloxy-3-methylpentane-<2-2H>-1,3-diol
• CAS No.: 123522-64-5
• Molecular Formula: C₁₃H₂₀O₃
• Molecular Weight: 225.292
• Mol file: 123522-64-5.mol

Synonyms:(2S,3R)-5-benzyloxy-3-methylpentane-<2-2H>-1,3-diol

Chemical Property of (2S,3R)-5-benzyloxy-3-methylpentane-<2-2H>-1,3-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-5-benzyloxy-3-methylpentane-<2-2H>-1,3-diol

There total 9 articles about (2S,3R)-5-benzyloxy-3-methylpentane-<2-2H>-1,3-diol 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: 90.0%

((2R,3R)-3-(2-(benzyloxy)ethyl)-3-methyloxiran-2-yl)methanol → (2S,3R)-5-benzyloxy-3-methylpentane-<2-2H>-1,3-diol (123522-64-5)

Guidance literature:

With lithium aluminium deuteride; In tetrahydrofuran; diethyl ether; at 0 ℃; for 3h;

DOI:10.1039/c3ob41755g

Reference yield:

((but-3-yn-1-yloxy)methyl)benzene (22273-77-4) → (2S,3R)-5-benzyloxy-3-methylpentane-<2-2H>-1,3-diol (123522-64-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 °C

1.2: -78 - 20 °C

2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 3 h / 0 - 20 °C

2.2: -78 - 0 °C

3.1: copper(l) iodide / tetrahydrofuran; diethyl ether / 6 h / 0 °C

4.1: D-(-)-diisopropyl tartrate; titanium(IV) isopropylate; Cumene hydroperoxide / dichloromethane / -23 °C / Molecular sieve

5.1: lithium aluminium deuteride / tetrahydrofuran; diethyl ether / 3 h / 0 °C

With titanium(IV) isopropylate; copper(l) iodide; n-butyllithium; lithium aluminium deuteride; Cumene hydroperoxide; D-(-)-diisopropyl tartrate; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; 4.1: |Sharpless Asymmetric Epoxidation;

DOI:10.1039/c3ob41755g

Reference yield:

benzyl bromide (100-39-0) → (2S,3R)-5-benzyloxy-3-methylpentane-<2-2H>-1,3-diol (123522-64-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydride / tetrahydrofuran / 0.17 h / 0 °C

1.2: 3.17 h / 0 - 20 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 °C

2.2: -78 - 20 °C

3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 3 h / 0 - 20 °C

3.2: -78 - 0 °C

4.1: copper(l) iodide / tetrahydrofuran; diethyl ether / 6 h / 0 °C

5.1: D-(-)-diisopropyl tartrate; titanium(IV) isopropylate; Cumene hydroperoxide / dichloromethane / -23 °C / Molecular sieve

6.1: lithium aluminium deuteride / tetrahydrofuran; diethyl ether / 3 h / 0 °C

With titanium(IV) isopropylate; copper(l) iodide; n-butyllithium; lithium aluminium deuteride; Cumene hydroperoxide; sodium hydride; D-(-)-diisopropyl tartrate; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; 5.1: |Sharpless Asymmetric Epoxidation;

DOI:10.1039/c3ob41755g

upstream raw materials:

benzyl bromide

C₉H₁₇⁽²⁾HO₃

(4R,5S)-4-(4-methyl-3-pentenyl)-2,2,4-trimethyl-<5-2H>-1,3-dioxane

(4R,5S)-4-(4-hydroxy-4-methyl-2-pentenyl)-2,2,4-trimethyl-<5-2H>-1,3-dioxane

Downstream raw materials:

(R)-5-O-benzyl-<2-2H>mevalonic acid