(S)-(-)-3-Benzyloxy-1,2-propanediol

Base Information

• Chemical Name: (S)-(-)-3-Benzyloxy-1,2-propanediol
• CAS No.: 17325-85-8
• Molecular Formula: C10H14O3
• Molecular Weight: 182.219
• Hs Code.: 2909499000
• European Community (EC) Number: 605-668-2
• DSSTox Substance ID: DTXSID90938348
• Nikkaji Number: J72.444K
• Wikidata: Q72442513
• ChEMBL ID: CHEMBL463584
• Mol file: 17325-85-8.mol

Synonyms:17325-85-8;(S)-(-)-3-Benzyloxy-1,2-propanediol;(S)-3-(benzyloxy)propane-1,2-diol;(2S)-3-phenylmethoxypropane-1,2-diol;(2S)-3-(benzyloxy)propane-1,2-diol;1,2-Propanediol, 3-(phenylmethoxy)-, (2S)-;1-O-Benzyl-sn-glycerol;1-O-Benzyl-L-glycerol;SCHEMBL508126;CHEMBL463584;DTXSID90938348;LWCIBYRXSHRIAP-JTQLQIEISA-N;MFCD00077914;AKOS015839325;AKOS015890371;(S)-(-)-Glycerol alpha-Benzyl Ether;CS-W017108;(2S)-3-(benzyloxy)-1,2-propanediol;AS-61375;B2142;1,2-Propanediol,3-(phenylmethoxy)-,(2S)-;E10198;(S)-(-)-3-Benzyloxy-1,2-propanediol, 99%;J-010891;(S)-(-)-3-Benzyloxy-1,2-propanediol, puriss., >=99.0% (sum of enantiomers, GC)

Chemical Property of (S)-(-)-3-Benzyloxy-1,2-propanediol

Chemical Property:

• Appearance/Colour: White to slightly yellow crystalline low meltingsolid
• Vapor Pressure: 1.17E-05mmHg at 25°C
• Melting Point: 24-26 °C(lit.)
• Refractive Index: -5.5 ° (C=20, CHCl3)
• Boiling Point: 355.1 °C at 760 mmHg
• PKA: 13.65±0.20(Predicted)
• Flash Point: 168.6 °C
• PSA: 49.69000
• Density: 1.16 g/cm³
• LogP: 0.55640
• Storage Temp.: 2-8°C
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 182.094294304
• Heavy Atom Count: 13
• Complexity: 121

Purity/Quality:

98%,99%, ^*data from raw suppliers

(S)-(-)-3-Benzyloxy-1,2-propanediol ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COCC(CO)O
• Isomeric SMILES: C1=CC=C(C=C1)COC[C@H](CO)O
• 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.

Technology Process of (S)-(-)-3-Benzyloxy-1,2-propanediol

There total 142 articles about (S)-(-)-3-Benzyloxy-1,2-propanediol 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: 100.0%

Benzyloxymethyl-oxiran (2930-05-4) + water-tetrahydrofuran → 3-benzyloxypropan-1,2-diol (13071-59-5,17325-85-8,56552-80-8,4799-67-1)

Guidance literature:

With sulfuric acid;

Reference yield: 99.0%

4-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolane (15028-56-5) → 3-benzyloxypropan-1,2-diol (13071-59-5,17325-85-8,56552-80-8,4799-67-1)

Guidance literature:

With hydrogenchloride; In methanol; at 20 ℃; for 2h;

DOI:10.1002/chem.202003991

Reference yield: 99.0%

4-phenylmethoxymethyl-1,3-dioxolan-2-one (949-97-3) → methanol (67-56-1) + 3-benzyloxypropan-1,2-diol (13071-59-5,17325-85-8,56552-80-8,4799-67-1)

Guidance literature:

With C₂₃H₂₁MnN₂O₃P⁽¹⁺⁾*Br^(1-); potassium tert-butylate; hydrogen; In 1,4-dioxane; at 140 ℃; for 16h; under 37503.8 Torr; Autoclave;

DOI:10.1002/anie.201805630

upstream raw materials:

oxiranyl-methanol

benzyl alcohol

4-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolane

benzyl chloride

Downstream raw materials:

(R)-1-benzyloxy-2,3-bis-oleoyloxy-propane

1-O-benzyl-2,3-di-O-dodecanoyl-rac-glycerol

1-[(2,3-dibromopropoxy)methyl]benzene

benzyloxyacetoaldehyde

Refernces

• 1、 Moreira, Ryan,Taylor, Scott D.. "The Chiral Target of Daptomycin Is the 2R,2′S Stereoisomer of Phosphatidylglycerol". . . Retrieved 2021/12/09.
• 2、 Chiosso, María E.,Casella, Mónica L.,Merlo, Andrea B.. "Synthesis and catalytic evaluation of acidic carbons in the etherification of glycerol obtained from biodiesel production". . p. 107 - 114. Retrieved 2020/10/29.