(R,R)-1,2,4,5-Diepoxypentane

Base Information

• Chemical Name: (R,R)-1,2,4,5-Diepoxypentane
• CAS No.: 109905-51-3
• Molecular Formula: C5H8 O2
• Molecular Weight: 100.117
• Mol file: 109905-51-3.mol

Synonyms:1,2:4,5-Dianhydro-3-deoxy-D-threo-pentitol

Chemical Property of (R,R)-1,2,4,5-Diepoxypentane

Chemical Property:

• Boiling Point: 80 °C (15 mmHg)
• PSA: 25.06000
• LogP: 0.17410

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (R,R)-1,2,4,5-Diepoxypentane

There total 19 articles about (R,R)-1,2,4,5-Diepoxypentane 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: 89.0%

(2S,4S)-1,5-dichloro-2,4-pentanediol (136030-29-0) → (2S,4S)-1,2:4,5-dianhydro-3-deoxypentitol (109905-51-3)

Guidance literature:

With potassium hydroxide; In diethyl ether; for 2h; Ambient temperature;

DOI:10.1016/0040-4039(96)01700-5

Reference yield: 69.0%

(2S,4S)-2,4-dihydroxypentane-1,5-diyl bis(2,4,6-triisopropyl-1-benzenesulfonate) (92512-29-3) → (2S,4S)-1,2:4,5-dianhydro-3-deoxypentitol (109905-51-3)

Guidance literature:

With sodium hydride; In tetrahydrofuran;

DOI:10.1021/jo9721655

Reference yield: 60.0%

(2S,4S)-pentane-1,2,3,4-tetraol (92691-36-6) → (2S,4S)-1,2:4,5-dianhydro-3-deoxypentitol (109905-51-3)

Guidance literature:

(2S,4S)-pentane-1,2,3,4-tetraol; With Acetyl bromide; In 1,4-dioxane; at 20 ℃; for 16h;

With potassium carbonate; In methanol; at 20 ℃; for 1h;

DOI:10.1016/S0040-4039(00)00237-9

upstream raw materials:

(2S,4S)-2,4-dihydroxypentane-1,5-diyl bis(2,4,6-triisopropyl-1-benzenesulfonate)

(2S,4S)-1,5-dichloro-2,4-pentanediol

(-)-(2R,4R)-1,2,4,5-pentanetetrol-1,5-bis-(4-methylbenzenesulphonate)

(2S,4S)-pentane-1,2,3,4-tetraol

Downstream raw materials:

(+)-α-<6-(tert-butyldiphenylsilyloxy)-3,5-dimethyl-2-hexenyl>oxiraneethanol

(3S,5R)-5-(hydroxymethyl)tetrahydrofuran-3-ol

(3S,5S)-5-(hydroxymethyl)tetrahydrofuran-3-ol

(2S,4S)-1,5-Bis-{2-[(R)-3-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-[1,3]dithian-2-yl}-pentane-2,4-diol

Refernces

• 1、 Walleser, Patrick,Brueckner, Reinhard. "Stereocontrolled synthesis of a C1-C10 building block ("Southwestern Moiety") for the unnatural enantiomers of the polyene polyol antibiotics filipin III and pentamycin: A sultone-forming ring-closing metathesis for protection of hom". . p. 3210 - 3224. Retrieved 2014/06/09.
• 2、 Rychnovsky, Scott D.,Griesgraber, George,Powers, Jay P.. "Preparation of (R,R)-1,2:4,5-diepoxypentane [ D-threo-Pentitol, 1,2:4,5-dianhydro-3-deoxy- ]". . p. 1 - 1. Retrieved 2017/10/06.