17325-85-8

Basic information

• Product Name: (S)-(-)-3-BENZYLOXY-1,2-PROPANEDIOL
• Synonyms: (S)-GLYCEROL 1-BENZYL ETHER;(S)-(-)-GLYCEROL ALPHA-BENZYL ETHER;(S)-(-)-1-BENZYLGLYCEROL;(S)-(-)-3-BENZYLOXY-1,2-PROPANEDIOL;(S)-3-BENZYLOXY-1,2-PROPANEDIOL;1-O-BENZYL-SN-GLYCEROL;1-BENZYL-SN-GLYCEROL;(S)-(-)-Benzylglycerol
• CAS NO: 17325-85-8
• Molecular Formula: C₁₀H₁₄O₃
• Molecular Weight: 182.22
• Product Categories: Heterocyclic Compounds;Chiral Building Blocks;Simple Alcohols (Chiral);Synthetic Organic Chemistry
• Mol File: 17325-85-8.mol
• Article Data: 161

Chemical Properties

• Melting Point: 24-26 °C(lit.)
• Boiling Point: 261 °C(lit.)
• Flash Point: >230 °F
• Appearance: White to slightly yellow crystalline low meltingsolid
• Density: 1.0966 (rough estimate)
• Vapor Pressure: 1.17E-05mmHg at 25°C
• Refractive Index: -5.5 ° (C=20, CHCl3)
• Storage Temp.: 2-8°C
• PKA: 13.65±0.20(Predicted)
• BRN: 2415534
• CAS DataBase Reference: (S)-(-)-3-BENZYLOXY-1,2-PROPANEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-3-BENZYLOXY-1,2-PROPANEDIOL(17325-85-8)
• EPA Substance Registry System: (S)-(-)-3-BENZYLOXY-1,2-PROPANEDIOL(17325-85-8)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 17325-85-8(Hazardous Substances Data)

Usage

Chemical Properties

white to slightly yellow crystalline low melting

Uses

(S)-(-)-3-Benzyloxy-1,2-propanediol is a useful building block. It is used in the preparation of the nucleotide analog (S)-1-[3-hydroxy-2-(phosphonylmethoxy)propyl]cystosine with antiviral activities. It is also used to synthesize cationic cardiolipin analogs with drug delivery systems such as transfection reagents.

Purification Methods

Purify the diol by repeated fractional distillation. [Baer et al. J Biol Chem 230 447 1958, Gigg & Gigg J Chem Soc C 1865 1967, Beilstein 6 IV 2247.]

InChI:InChI=1/C10H14O3/c11-6-10(12)8-13-7-9-4-2-1-3-5-9/h1-5,10-12H,6-8H2/t10-/m0/s1

Upstream product

• 556-52-5 oxiranyl-methanol 
• 100-51-6 benzyl alcohol 
• 100-44-7 benzyl chloride 
• 100-79-8 (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol 
• 2930-05-4 Benzyloxymethyl-oxiran 
• 1708-40-3 2-phenyl-[1,3]dioxan-5-ol 
• 949-97-3 4-phenylmethoxymethyl-1,3-dioxolan-2-one 
• 109-65-9 1-bromo-butane 
• 108-86-1 bromobenzene 
• 53963-10-3 2-[(6-bromohexyl)oxy]tetrahydro-2H-pyran 
• 507-20-0 tertiary butyl chloride 
• 112-29-8 1-bromo dodecane 
• 75-26-3 isopropyl bromide 
• 1708-40-3 cis-5-hydroxyl-2-phenyl-1,3-dioxane 

Downstream Products

• 103397-09-7 1-O-benzyl-2,3-di-O-dodecanoyl-rac-glycerol 
• 60276-38-2 1-[(2,3-dibromopropoxy)methyl]benzene 
• 60656-87-3 benzyloxyacetoaldehyde 
• 209802-30-2 (+/-)-1-benzyloxy-2,3-bis-methanesulfonyloxy-propane 
• 73083-33-7 1,2-di-O-myristoyl-3-O-benzyl-sn-glycerol 
• 73083-33-7 3-(benzyloxy)propane-1,2-diyl ditetradecanoate 
• 6236-22-2 1-benzyloxy-3-stearoyloxy-propan-2-ol 
• 76189-95-2 3-O-benzyl-1,2-di-O-stearoyl-rac-glycerol 
• 142924-85-4 α-Oleonyl-α'-benzyl-glycerin 
• 121348-74-1 1-O-benzyl-2-O-methyl-rac-glycerol 
• 28959-03-7 1-benzyloxy-2,3-dimethoxypropane 
• 36680-64-5 1-O-Palmitoyl-3-O-benzyl-2-propanon 
• 143003-65-0 (2R)-3-(benzyloxy)-2-hydroxypropyl hexadecanoate 
• 949-97-3 4-phenylmethoxymethyl-1,3-dioxolan-2-one 

Relevant articles and documents

Dispiroketals in synthesis (Part 15): Simultaneous enantioselective and regioselective protection of glycerol by reaction with C2 symmetric (4S,4'S)-dimethyl-bis-dihydropyran

Glycerol was simultaneously, enantioselectively and regioselectively protected by reaction with (4S,4'S)-4,4'-dimethyl-3,3',4,4'-tetrahydro-6,6'-bis-2H-pyran to afford a dispiroketal product.

Total Synthesis of the Alleged Structure of Crenarchaeol Enables Structure Revision**

Crenarchaeol is a glycerol dialkyl glycerol tetraether lipid produced exclusively in Archaea of the phylum Thaumarchaeota. This membrane-spanning lipid is undoubtedly the structurally most sophisticated of all known archaeal lipids and an iconic molecule in organic geochemistry. The 66-membered macrocycle possesses a unique chemical structure featuring 22 mostly remote stereocenters, and a cyclohexane ring connected by a single bond to a cyclopentane ring. Herein we report the first total synthesis of the proposed structure of crenarchaeol. Comparison with natural crenarchaeol allowed us to propose a revised structure of crenarchaeol, wherein one of the 22 stereocenters is inverted.

Acylative desymmetrization of glycerol derivatives by chiral dmap derivatives

An efficient enantioselective acylative desymmetrization of glycerol was developed by using a chiral DMAP derivatives 1e having a 1,1-binaphthyl unit. The reactions required only 0.1 mol% of the catalyst and showed moderate to good enantioselectivity (up