erythro-(2R,3S)-1-(Tosyloxy)-2,3-tetradecanediol

Base Information

• Chemical Name: erythro-(2R,3S)-1-(Tosyloxy)-2,3-tetradecanediol
• CAS No.: 117316-14-0
• Molecular Formula: C₂₁H₃₆O₅S
• Molecular Weight: 400.58
• Mol file: 117316-14-0.mol

Synonyms:erythro-(2R,3S)-1-(Tosyloxy)-2,3-tetradecanediol

Chemical Property of erythro-(2R,3S)-1-(Tosyloxy)-2,3-tetradecanediol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of erythro-(2R,3S)-1-(Tosyloxy)-2,3-tetradecanediol

There total 1 articles about erythro-(2R,3S)-1-(Tosyloxy)-2,3-tetradecanediol 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: 53.0%

(2R,3R,S)-1,2,3-Tetradecanetriol (92318-78-0,117286-13-2,117316-13-9,150960-19-3) + p-toluenesulfonyl chloride (98-59-9) → erythro-(2R,3S)-1-(Tosyloxy)-2,3-tetradecanediol (117316-14-0)

Guidance literature:

With pyridine; at 5 ℃; for 72h;

DOI:10.1021/jo00071a026

Reference yield:

erythro-(2R,3S)-1-(Tosyloxy)-2,3-tetradecanediol (117316-14-0) → (2R,3S)-1,2-epoxy-3-(tosyloxy)tetradecane (117286-14-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / K₂CO₃ / methanol / 3.5 h / Ambient temperature

2: 41 percent / pyridine / 41 h / 5 °C

With pyridine; potassium carbonate; In methanol;

DOI:10.1021/jo00071a026

Reference yield:

erythro-(2R,3S)-1-(Tosyloxy)-2,3-tetradecanediol (117316-14-0) → (9S,10S)-9-hydroxy-10-tosyloxyheneicosadec-6-yne (162758-32-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / K₂CO₃ / methanol / 3.5 h / Ambient temperature

2: 41 percent / pyridine / 41 h / 5 °C

3: n-BuLi, BF₃*Et₂O / tetrahydrofuran; hexane / 4.5 h / -78 °C

With pyridine; n-butyllithium; boron trifluoride diethyl etherate; potassium carbonate; In tetrahydrofuran; methanol; hexane;

DOI:10.1021/jo00071a026

upstream raw materials:

(2R,3R,S)-1,2,3-Tetradecanetriol

p-toluenesulfonyl chloride

Downstream raw materials:

(2R,3S)-1,2-epoxy-3-(tosyloxy)tetradecane

(9S,10S)-9-hydroxy-10-tosyloxyheneicosadec-6-yne

(9S,10S)-9-hydroxy-10-(tosyloxy)henicosa-3,6-diyne