(S,S)-1,2-dicyclohexylethanediol (R)-[1-(benzyloxy)ethyl]boronate

Base Information

• Chemical Name: (S,S)-1,2-dicyclohexylethanediol (R)-[1-(benzyloxy)ethyl]boronate
• CAS No.: 181782-56-9
• Molecular Formula: C₂₃H₃₅BO₃
• Molecular Weight: 370.34
• Mol file: 181782-56-9.mol

Synonyms:

Chemical Property of (S,S)-1,2-dicyclohexylethanediol (R)-[1-(benzyloxy)ethyl]boronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,S)-1,2-dicyclohexylethanediol (R)-[1-(benzyloxy)ethyl]boronate

There total 1 articles about (S,S)-1,2-dicyclohexylethanediol (R)-[1-(benzyloxy)ethyl]boronate 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:

(S,S)-(-)-1,2-dicyclohexyl-ethane-1,2-diol (120850-91-1) + (R,R)-1,2-dicyclohexylethanediol (R)-[1-(benzyloxy)ethyl]boronate (181515-46-8) → (1R,2R)-1,2-dicyclohexyl-1,2-ethanediol (120850-92-2) + (S,S)-1,2-dicyclohexylethanediol (R)-[1-(benzyloxy)ethyl]boronate (181782-56-9)

Guidance literature:

(R,R)-1,2-dicyclohexylethanediol (R)-[1-(benzyloxy)ethyl]boronate; With sodium hydroxide; Pentaerythritol; 3-{[tris(hydroxymethyl)methyl]amino}propanesulfonic acid; In diethyl ether; water; at 20 ℃; for 18h;

With hydrogenchloride; water; at 0 ℃; pH=3;

(S,S)-(-)-1,2-dicyclohexyl-ethane-1,2-diol; In hexane; for 18h;

DOI:10.1021/jo960684m

Reference yield:

(S,S)-1,2-dicyclohexylethanediol (R)-[1-(benzyloxy)ethyl]boronate (181782-56-9) → (S,S)-(-)-1,2-dicyclohexyl-ethane-1,2-diol (120850-91-1)

Guidance literature:

Multi-step reaction with 5 steps

3.1: butyllithium / tetrahydrofuran / -100 °C

3.2: 47 g / zinc chloride / tetrahydrofuran / 36 h / -100 - 20 °C

4.1: 32.3 g / tetrahydrofuran / 48 h / -78 - 25 °C

5.1: sodium hydroxide; hydrogen peroxide / tetrahydrofuran; H₂O / 18 h / 0 - 20 °C

With sodium hydroxide; n-butyllithium; dihydrogen peroxide; In tetrahydrofuran; water; 1.1: insertion / 2.1: Substitution / 3.1: Metallation / 3.2: insertion / 4.1: Substitution / 5.1: Oxidation;

DOI:10.1021/jo960684m

Reference yield:

(S,S)-1,2-dicyclohexylethanediol (R)-[1-(benzyloxy)ethyl]boronate (181782-56-9) → (3R,4S,5S)-5-(benzyloxy)-4-methyl-3-hexanol

Guidance literature:

Multi-step reaction with 5 steps

3.1: butyllithium / tetrahydrofuran / -100 °C

3.2: 47 g / zinc chloride / tetrahydrofuran / 36 h / -100 - 20 °C

4.1: 32.3 g / tetrahydrofuran / 48 h / -78 - 25 °C

5.1: 86 percent / sodium hydroxide; hydrogen peroxide / tetrahydrofuran; H₂O / 18 h / 0 - 20 °C

With sodium hydroxide; n-butyllithium; dihydrogen peroxide; In tetrahydrofuran; water; 1.1: insertion / 2.1: Substitution / 3.1: Metallation / 3.2: insertion / 4.1: Substitution / 5.1: Oxidation;

DOI:10.1021/jo960684m

upstream raw materials:

(S,S)-(-)-1,2-dicyclohexyl-ethane-1,2-diol

(R,R)-1,2-dicyclohexylethanediol (R)-[1-(benzyloxy)ethyl]boronate

Downstream raw materials:

(S,S)-(-)-1,2-dicyclohexyl-ethane-1,2-diol

(S,S)-1,2-dicyclohexylethanediol (1R,2S)-[2-(benzyloxy)-1-methylpropyl]boronate

(S,S)-1,2-dicyclohexylethanediol (1R,2S,3S)-{[3-(benzyloxy)-2-methyl-1-ethyl]butyl}boronate