20196-71-8

Usage

Uses

Used in Organic Chemistry:
(S)-(-)-1,2-Di-O-benzylglycerol is used as a building block for the synthesis of various organic molecules, such as pharmaceuticals, fragrances, and polymers. Its unique structure allows for versatile chemical modifications and functionalization, making it a valuable component in the development of new compounds.
Used as a Protecting Group:
In organic chemistry, (S)-(-)-1,2-Di-O-benzylglycerol serves as a protecting group for the hydroxyl groups in glycerol. This protects the hydroxyl groups from unwanted reactions during the synthesis process, ensuring the desired product is obtained with minimal side reactions.
Used as a Reagent in Organic Reactions:
(S)-(-)-1,2-Di-O-benzylglycerol is utilized as a reagent in various organic reactions, facilitating the formation of desired products and improving the efficiency of the reaction process.
Used in Pharmaceutical Synthesis:
As a key intermediate, (S)-(-)-1,2-Di-O-benzylglycerol is involved in the preparation of numerous biologically active compounds, contributing to the development of new pharmaceuticals with potential therapeutic applications.
Used in Academic and Industrial Research:
(S)-(-)-1,2-Di-O-benzylglycerol has applications in both academic and industrial research settings, where it is employed for the exploration of new chemical reactions, the synthesis of novel compounds, and the investigation of their properties and potential uses.

Upstream product

• 20196-70-7 (+)-(R)-2,3-bis(benzyloxy)propanal 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 133174-17-1 (2'S)-2'-O-(tetradecanoyl)-3'-O-(9Z,12Z,15Z-octadecatrienoyl)-glyceryl-β-D-galactopyranoside 
• 162018-24-8 2-((R)-2,3-Bis-benzyloxy-propoxy)-tetrahydro-pyran 
• 20196-69-4 1,2,5,6-tetra-O-benzyl-D-mannitol 
• 83000-61-7 1-stearoyl-2-O-benzyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-sn-glycerol 
• 126786-46-7 1,2-di-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)glycerol 
• 81093-32-5 1,2-di-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-sn-glycerol 
• 123427-34-9 (4S,5R,2'R)-1,5-dimethyl-4-phenyl-3-(2'3'-dibenzyloxypropanoyl)imidazolidin-2-one 
• 59541-19-4 1,2-di-O-benzyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-sn-glycerol 
• 20196-69-4 1,2,5,6-tetra-O-benzyl-D-mannitol 
• 3969-84-4 3,4-di-O-isopropylidene-D-mannitol 
• 81093-29-0 1-stearoyl-2-O-benzyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-sn-glycerol 

Downstream Products

• 63121-17-5 ((R)-2,3-Bis-benzyloxy-propoxy)-tert-butyl-dimethyl-silane 
• 96429-72-0 1-O-(chloromethyl)-2,3-di-O-benzyl-D-glycerol 
• 55955-33-4 (2R)-1,2-di-O-benzyl-3-O-(2′,3′,4′,6′-tetra-O-acetyl-β-D-galactopyranosyl)glycerol 
• 210765-72-3 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-((R)-2,3-bis-benzyloxy-propoxy)-tetrahydro-pyran-4-yl ester 
• 175877-63-1 (R)-2,3-dibenzyloxypropyl 5-bromo-5-deoxy-2,3-O-isopropylidene-β-D-riboside 
• 370860-11-0 (R)-2,3-dibenzyloxypropyl 5-chloro-5-deoxy-2,3-O-isopropylidene-β-D-riboside 
• 832719-96-7 Acetic acid (2R,3R,4S,5S,6R)-3,5-diacetoxy-2-((R)-2,3-bis-benzyloxy-propoxy)-6-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-4-yl ester 
• 1029440-06-9 C₂₉H₃₄BFO₅ 
• 197306-92-6 1-octadecyl-2,3-dibenzylglycerol 
• 174289-76-0 1-hexadecyl-2,3-dibenzylglycerol 
• 58438-08-7 (2R)-1,2-di-O-benzyl-3-O-(2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyranosyl)glycerol 
• 60598-98-3 1,2-di-O-benzyl-3-O-triphenylmethyl-sn-glycerol 
• 96429-71-9 1,2-di-O-benzyl-3-O-triphenylmethyl-sn-glycerol 
• 123394-81-0 (R)-1-propanoyloxy-2,3-dibenzyloxypropane 

Relevant academic research and scientific papers

A latent reactive handle for functionalising heparin-like and LMWH deca- and dodecasaccharides

d-Glucosamine derivatives bearing latent O4 functionality provide modified H/HS-type disaccharide donors for a final stage capping approach enabling introduction of conjugation-suitable, non-reducing terminal functionality to biologically important glycosaminoglycan oligosaccharides. Application to the synthesis of the first O4-terminus modified synthetic LMWH decasaccharide and an HS-like dodecasaccharide is reported.

Synthesis of N-oxyamide-linked neoglycolipids

N-Oxyamide-containing compounds have shown improved metabolic stability and interesting secondary structures due to the good hydrogen bond-donating property of N-oxyamide. β-Glucolipids linked by the N-oxyamide bond have been successfully synthesized as novel mimics of glycoglycerolipids and glycosphingolipids.

Total synthesis of (-)-Pramanicin

The total synthesis of natural (-)-pramanicin, a highly oxygenated γlactam-type antifungal agent, is described. The enantiospecific total synthesis of this natural product commenced with 5-deoxy-1,2-O-isopropylidene-α-d-xylofuranose as an enantiopure star

Synthesis of biologically active galactosyl and glucosyl-glycerol derivatives

Galactosyl and glucosyl-glycerol derivatives which mimic the structure of the lipoteichoic acid of Staphylococcus aureus were synthesized by using a chiral glycerol derivative. Glucosyl-glycerol derivatives (14 and 22) had stronger anti-inflammatory activ

Studies on glycolipids. III. Glyceroglycolipids from an axenically cultured cyanobacterium, Phormidium tenue

Seven new monogalactosyl diacylglycerols (1-7) and six new digalactosyl diacylglycerols (11-16) were isolated from an axenically cultured cyanobacterium, P. tenue. Their structures were elucidated on the basis of physicochemical evidence and the results of enzymatic hydrolysis using a lipase (from Rhizopus arrhizus). Comparison of antialgal activity for P. tenue between monogalactosyl diacylglycerols (1-8) and digalactosyl diacylglycerols (11-19) revealed that the former showed more potent activity than the latter.

ENANTIOSELECTIVE SYNTHESIS OF 2-BENZYLOXY ALCOHOLS AND 1,2-DIOLS VIA ALKYLATION OF CHIRAL GLYCOLATE IMIDES. A CONVENIENT APPROACH TO OPTICALLY ACTIVE GLYCEROL DERIVATIVES

The alkylation of the chiral enolates of glycolate imides 2a and 2b proceedes in highly diastereoselective manner to give 2'-substituted products in good yield.Reductive cleavage with LiBH4 affords the corresponding 2-benzyloxyalcohols 3a-c and 11a-b which are successively converted to 1,2-diols in high optical purity.By this method (R)-1-propanoyloxy-2,3-propanediol 9 and (S)-1-tridecyloxy-2,3-propanediol 14, a glyceride extracted from sponges Plocamiidae, have been synthesized, starting from 2a and 2b, respectively.

Simple Method to Detrermine the Absolute Configuration of the Glycerol Moiety in Glycosyl Glycerols Based On ORD and CD

A general method to determine the absolute configuration of the glycerol moiety in glycopyranosyl glycerols is presented, which involves per-O-benzylation and acid hydrolysis of the glycosyl glycerol to give optically active 1,2- or 2,3-di-O-benzylated sn-glycerol (III).ORD and CD measurements of III and its benzoylated derivatives gave intensive optical rotations or Cotton effects to determine the absolute configuration at C2.

The Synthesis of (R)-2',3'-Dihydroxypropyl 5-Deoxy-5-dimethylarsinyl-β-D-riboside, a Naturally Occurring Arsenic-Containing Carbohydrate

The synthesis of the title compound, isolated from the brown kelp (Ecklonia radiata) or the giant clam (Tridacna maxima), is reported.Glycosidation of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribose, either directly with (S)-1,2-di-O-benzylglycerol or via the derived orthoester with (S)-1,2-O-isopropylideneglycerol, led to two fully protected glycerol β-D-ribofuranosides.Subsequent chemical manipulations led to a common intermediate having a free hydroxy group at C 5 of the D-ribose residue.Replacement of this hydroxy group by a chlorine atom allowed the introduction of the dimethylarsinyl group at C 5 in a two-step procedure, and removal of protecting groups provided the natural product.

THE SYNTHESIS OF (R)-2',3'-DIHYDROXYPROPYL 5-DEOXY-5-DIMETHYLARSINOYL-β-D-RIBOSIDE, A NATURALLY-OCCURING, ARSENIC-CONTAINING CARBOHYDRATE

The synthesis of (R)-2',3'-dihydroxypropyl 5-deoxy-5-dimethylarsinoyl-β-D-riboside is reported.

Synthesis and antiherpetic activity of (S)-, (R)- and (±)-9-[(2,3-dihydroxy-1-propoxy)methyl]guanine, linear isomers of 2'-nor-2'-deoxyguanosine

Racemic 9-[2,3-dihydroxy-1-propoxy)methyl]guanine [(±)-iNDG], a new analogue of acyclovir (ACV) and a structural analogue of 2'-nor-2'-deoxyguanosine (2'NDG), was synthesized and found to inhibit the replication of herpes simplex virus types 1 (HSV-1) and 2 (HSV-2). Subsequently, its optical isomers, (R)- and (S)-iNDG, were prepared from chiral intermediates. The chloromethyl ethers of 1,2-di-O-benzyl-D- and -L-glycerol were made and reacted with tris(trimethylsilyl)guanine to give the 9-alkylated guanines, which were deprotected by catalytic hydrogenolysis. Against HSV-1 and HSV-2 in cell culture, (S)-iNDG was approximately 10- to 25-fold more active than the R enantiomer and had an ED50 comparable to those for ACV and 2'NDG. The inferior activity of (R)-iNDG paralleled the poor inhibition of viral DNA polymerase by its phosphorylation products. In mice infected intraperitoneally or orofacially with HSV-1 or intravaginally with HSV-2, (S)-9-[(2,3-dihydroxy-1-propoxy)methyl]guanine [(S)-iNDG] was less efficacious than 2'NDG but comparable to or more active than ACV.