Methyl 3-O-Benzyl-D-glycerate

Base Information

• Chemical Name: Methyl 3-O-Benzyl-D-glycerate
• CAS No.: 209907-54-0
• Molecular Formula: C11H14O4
• Molecular Weight: 210.23
• Mol file: 209907-54-0.mol

Synonyms:Methyl3-O-Benzyl-D-glycerate;methyl (2R)-2-hydroxy-3-phenylmethoxypropanoate;

Chemical Property of Methyl 3-O-Benzyl-D-glycerate

Chemical Property:

• Appearance/Colour: Colourless to Yellow Oil
• PSA: 55.76000
• LogP: 0.73710
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), DMSO (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

Methyl3-O-Benzyl-D-glycerate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl 3-O-Benzyl-D-glycerate (cas# 209907-54-0) is a compound useful in organic synthesis.

Technology Process of Methyl 3-O-Benzyl-D-glycerate

There total 4 articles about Methyl 3-O-Benzyl-D-glycerate 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: 87.0%

3-(benzyloxy)-(R)-2-hydroxy-propionic acid (127744-27-8,130111-08-9) + trimethyl orthoformate (149-73-5) → methyl (2R)-3-benzyloxy-2-hydroxypropanoate (209907-54-0)

Guidance literature:

With hydrogenchloride; In methanol; at 20 ℃; for 18h;

DOI:10.1016/j.tetasy.2008.06.030

Reference yield:

methyl (2R)-2,3-dihydroxypropanoate (18289-89-9,15909-76-9) + benzyl bromide (100-39-0) → methyl (2R)-3-benzyloxy-2-hydroxypropanoate (209907-54-0) + methyl 2-O-benzyl-D-glycerate + benzyl (2R)-2-hydroxy-3-benzyloxypropanoate + benzyl alcohol (100-51-6,185532-71-2)

Guidance literature:

With di(n-butyl)tin oxide; N,N-dimethyl-formamide; cesium fluoride; Yield given. Multistep reaction. Yields of byproduct given; 1.) chloroform, methanol, reflux, 3 h; 2.) 17 h, RT;

DOI:10.3891/acta.chem.scand.52-0819

Reference yield:

methyl (2R)-2,3-dihydroxypropanoate (18289-89-9,15909-76-9) + benzyl bromide (100-39-0) → Benzyl acetate (140-11-4) + methyl (2R)-3-benzyloxy-2-hydroxypropanoate (209907-54-0) + methyl 2-O-benzyl-D-glycerate

Guidance literature:

With silver(I) acetate; di(n-butyl)tin oxide; N,N-dimethyl-formamide; cesium fluoride; Product distribution; Mechanism; 1.) CHCl₃, MeOH, reflux; 2.) RT, 17 h; study of selective monobenzylation with various benzyl halides, solvents and without AcOAg;

DOI:10.3891/acta.chem.scand.52-0819

upstream raw materials:

methyl (2R)-2,3-dihydroxypropanoate

benzyl bromide

diazomethane

3-(benzyloxy)-(R)-2-hydroxy-propionic acid

Downstream raw materials:

methyl (2S)-3-benzyloxy-2-[4'-(tert-butoxycarbonyl)-1'-piperazinyl]propanoate

Refernces

• 1、 Arukwe, Joseph. "The effect of cesium fluoride-DMF in the dibutylstannylene acetal-mediated selective monobenzylation of methyl 2,3-D-glycerate". . p. 819 - 823. Retrieved 2007/10/03.