(S)-(+)-2,2-Dimethyl-1,3-dioxolane-4-methanol

Base Information

• Chemical Name: (S)-(+)-2,2-Dimethyl-1,3-dioxolane-4-methanol
• CAS No.: 22323-82-6
• Molecular Formula: C6H12O3
• Molecular Weight: 132.159
• Hs Code.: 29329970
• European Community (EC) Number: 244-910-8
• DSSTox Substance ID: DTXSID701317976
• Nikkaji Number: J208.400G
• Mol file: 22323-82-6.mol

Synonyms:22323-82-6;(S)-(+)-2,2-Dimethyl-1,3-dioxolane-4-methanol;[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol;s-glycerol acetonide;(S)-(+)-1,2-Isopropylideneglycerol;(S)-2,2-Dimethyl-1,3-dioxolane-4-methanol;(+)-Solketal;1,2-Isopropylidene-sn-glycerol;1,3-Dioxolane-4-methanol, 2,2-dimethyl-, (4S)-;(s)-(+)-2,3-o-isopropylideneglycerol;(S)-(2,2-dimethyl-1,3-dioxolan-4-yl)methanol;EINECS 244-910-8;D-Acetone glycerol;MFCD00063239;R-(-)-Sollketal;(S)-Solketal;(S)-Glycerol-acetonide;1,3-Dioxolane-4-methanol, 2,2-dimethyl-, (S)-;SCHEMBL221388;1,2-o-isopropylidene-sn-glycerol;AM856;DTXSID701317976;1,2-o-iso-propylidene-sn-glycerol;D-(+)-1,2-Isopropylideneglycerol;GEO-01176;MFCD00063748;AKOS005257632;AC-6134;CS-W013415;AS-14052;BP-11488;D1691;EN300-86444;A23564;F11426;I-8360;S(+)2,2-dimethyl -1,3-dioxolane-4-methanol;(4S)-2,2-Dimethyl-1,3-dioxolan-4-ylmethanol;(4S )-2,2-dimethyl-1,3-dioxolan-4-ylmethanol;(S)-(+)-2,2-dimethyl-1,3-dioxolan-4-methanol;(s)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol;A816104;((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-methanol;(2,2-Dimethyl-1,3-dioxolan-4-yl)methanol, (L)-;(s)-(+)-2,2,-dimethyl-1,3-dioxolane-4-methanol;(S)-(+)-2,2-Dimethyl-1,3-dioxaolane-4-methanol;(S)-(2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol;((4S)-2,2-dimethyl-1,3-dioxolan-4-yl)methan-1-ol;(4S)-2,2-DIMETHYL-1,3-DIOXOLANE-4-METHANOL;(S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol;(S)-(+)-2,2-dimethyl-4-(hydroxymethyl)-1,3-dioxolane;(+/-)-2,2-Dimethyl-1,3-dioxolane-4-methanol (Glycerol acetonide);(4S)-(+)-2,2-Dimethyl-4-(hydroxymethyl)-1,3-dioxolane 98%;(S)-(+)-1,2-Isopropylideneglycerol, 98%, optical purity ee: 99% (GLC)

Chemical Property of (S)-(+)-2,2-Dimethyl-1,3-dioxolane-4-methanol

Chemical Property:

• Appearance/Colour: Colorless oil
• Refractive Index: n20/D 1.434
• Boiling Point: 188.5 °C at 760 mmHg
• PKA: 14.20±0.10(Predicted)
• Flash Point: 80 °C
• PSA: 38.69000
• Density: 1.034 g/cm³
• LogP: 0.13020
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Ethanol, Methanol
• Water Solubility.: miscible
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 132.078644241
• Heavy Atom Count: 9
• Complexity: 101

Purity/Quality:

98% ^*data from raw suppliers

(S)-(+)-2,2-Dimethyl-1,3-dioxolane-4-methanol ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(OCC(O1)CO)C
• Isomeric SMILES: CC1(OC[C@@H](O1)CO)C
• Uses: (S)-(+)-2,3-O-Isopropylideneglycerol acts as a MEK inhibitor with antitumor activity. It is also employed in the preparation of a chiral allylic triol through extrusion of sulfur dioxide from an alfa,beta-epoxysulfone. A MEK inhibitor with antitumor activity

Technology Process of (S)-(+)-2,2-Dimethyl-1,3-dioxolane-4-methanol

There total 79 articles about (S)-(+)-2,2-Dimethyl-1,3-dioxolane-4-methanol 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:

(2,2-dimethyl-1,3-dioxolan-4-yl)methyl acetate (57415-98-2,14739-11-8) → (S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol (22323-82-6,36543-79-0) + 1,2-O-isopropylidene-D-glycerol (14347-78-5,36543-79-0)

Guidance literature:

With phosphate buffer; porcine pancreas; at 28 ℃; Title compound not separated from byproducts;

DOI:10.1021/ja00229a041

Reference yield:

(2,2-dimethyl-1,3-dioxolane-4-yl)methyl caproate (20620-19-3) → (S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol (22323-82-6,36543-79-0) + 1,2-O-isopropylidene-D-glycerol (14347-78-5,36543-79-0)

Guidance literature:

With methanol; In di-isopropyl ether; at 0 ℃; for 83h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1016/S0957-4166(97)00057-8

Reference yield:

(+/-)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl n-octadecanoate (10567-18-7,32852-69-0,111425-86-6,136656-03-6) → (S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol (22323-82-6,36543-79-0) + 1,2-O-isopropylidene-D-glycerol (14347-78-5,36543-79-0)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 12h;

DOI:10.1002/ejoc.201300247

upstream raw materials:

2,3-isopropylidene-glyceraldehyde

(R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol

methyl (R)-2,2-dimethyl-1,3-dioxolane-4-carboxylate

(2,2-dimethyl-1,3-dioxolan-4-yl)methyl 2-phenylacetate

Downstream raw materials:

(R)-2,3-bis(((9Z,12Z)-octadeca-9,12-dienoyl)oxy)propyl (2-(trimethylammonio)ethyl) phosphate

C₃₂H₃₂O₁₀

3-O-dodecyl-sn-glycerol

C₃₂H₃₂O₁₀

Refernces

• 1、 Martins, Rafaela de S.,Pereira, Mathias P.,de Castro, Pedro P.,Bombonato, Fernanda I.. "Design and preparation of a novel prolinamide-based organocatalyst for the solvent-free asymmetric aldol reaction". . . Retrieved 2019/12/24.
• 2、 De Vitis, Valerio,Nakhnoukh, Cristina,Pinto, Andrea,Contente, Martina L.,Barbiroli, Alberto,Milani, Mario,Bolognesi, Martino,Molinari, Francesco,Gourlay, Louise J.,Romano, Diego. "A stereospecific carboxyl esterase from Bacillus coagulans hosting nonlipase activity within a lipase-like fold". . p. 903 - 914. Retrieved 2018/01/22.