1,2-Propanediol, 3-(dodecyloxy)-, (R)-

Base Information

• Chemical Name: 1,2-Propanediol, 3-(dodecyloxy)-, (R)-
• CAS No.: 90904-23-7
• Molecular Formula: C15H32O3
• Molecular Weight: 260.41300
• Mol file: 90904-23-7.mol

Synonyms:(-)-3-dodecyloxy-propane-1,2-diol;(-)-3-Dodecyloxy-propan-1,2-diol;(-)-O1-Dodecyl-glycerin;3-O-dodecyl-sn-glycerol;(R)-3-Dodecyloxy-propane-1,2-diol;

Chemical Property of 1,2-Propanediol, 3-(dodecyloxy)-, (R)-

Chemical Property:

• Boiling Point: 390.5±22.0 °C(Predicted)
• PSA: 49.69000
• Density: 0.937±0.06 g/cm3(Predicted)
• LogP: 3.27710

Purity/Quality:

3-O-Dodecyl-sn-glycerol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3-O-Dodecyl-sn-glycerol is used in the preparation of cysteine based lipopeptides and compositions as TLR2 agonists useful for treating infections, inflammations, respiratory, dermatological and autoimmune diseases.

Technology Process of 1,2-Propanediol, 3-(dodecyloxy)-, (R)-

There total 5 articles about 1,2-Propanediol, 3-(dodecyloxy)-, (R)- 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: 99.0%

3-O-dodecyl-1,2-O-isopropylidene-sn-glycerol (478549-98-3) → 3-O-dodecyl-sn-glycerol (90904-23-7,1561-07-5)

Guidance literature:

With 80percent aq. AcOH; at 20 ℃;

DOI:10.1021/ja020396+

Reference yield: 31.8%

1-dodecyl alcohol (112-53-8) + (R)-oxiranemethanol (57044-25-4) → 3-O-dodecyl-sn-glycerol (90904-23-7,1561-07-5)

Guidance literature:

1-dodecyl alcohol; With diisobutylaluminium hydride; In hexane; dichloromethane; for 1h; Cooling with ice;

(R)-oxiranemethanol; In hexane; dichloromethane; at 20 ℃; for 72h;

With water; Rochelle's salt; In hexane; dichloromethane; for 0.5h;

DOI:10.1016/j.bmc.2009.03.030

Reference yield:

1-dodecylbromide (143-15-7) → 3-O-dodecyl-sn-glycerol (90904-23-7,1561-07-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / 50percent aq. NaOH; tetrabutylammonium bromide / 20 h / 80 °C

2: 99 percent / 80percent aq. AcOH / 20 °C

With tetrabutylammomium bromide;

DOI:10.1021/ja020396+

upstream raw materials:

dodecyl mesylate

(S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol

3-O-dodecyl-1,2-O-isopropylidene-sn-glycerol

1-dodecylbromide

Downstream raw materials:

3-O-Dodecyl-1-O-trityl-sn-glycerin

2-azido-2-deoxy-1-O-dodecyl-sn-glycerol

2-azido-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2-deoxy-1-O-dodecyl-sn-glycerol

3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2-deoxy-2-dodecanamido-1-O-dodecyl-sn-glycerol

Refernces

• 1、 Dumoulin, Fabienne,Lafont, Dominique,Boullanger, Paul,Mackenzie, Grahame,Mehl, Georg H.,Goodby, John W.. "Self-organizing properties of natural and related synthetic glycolipids". . p. 13737 - 13748. Retrieved 2007/10/03.