(R)-4-Benzyloxymethyl-2,2-dimethyl-1,3-dioxolane

Base Information

• Chemical Name: (R)-4-Benzyloxymethyl-2,2-dimethyl-1,3-dioxolane
• CAS No.: 14347-83-2
• Molecular Formula: C13H18O3
• Molecular Weight: 222.284
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID70931897
• Nikkaji Number: J2.642.271J
• Wikidata: Q82907508
• Mol file: 14347-83-2.mol

Synonyms:14347-83-2;(R)-4-Benzyloxymethyl-2,2-dimethyl-1,3-dioxolane;(R)-4-((Benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolane;(R)-4-(Benzyloxymethyl)-2,2-dimethyl-1,3-dioxolane;(4R)-2,2-dimethyl-4-(phenylmethoxymethyl)-1,3-dioxolane;SCHEMBL5606199;DTXSID70931897;DBFDSKSLTCMIPB-GFCCVEGCSA-N;MFCD00066533;AKOS015839326;AKOS015911809;AS-46689;A3100;B2136;CS-0328725;E10197;1,3-Dioxolane,2,2-dimethyl-4-[(phenylmethoxy)methyl]-,(4R)-;1,3-Dioxolane, 2,2-dimethyl-4-[(phenylmethoxy)methyl]-, (4R)-;4-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolane

Chemical Property of (R)-4-Benzyloxymethyl-2,2-dimethyl-1,3-dioxolane

Chemical Property:

• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: n20/D 1.496
• Boiling Point: 300.306 °C at 760 mmHg
• Flash Point: 99.967 °C
• PSA: 27.69000
• Density: 1.039 g/cm³
• LogP: 2.35470
• Storage Temp.: 2-8°C
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 222.125594432
• Heavy Atom Count: 16
• Complexity: 209

Purity/Quality:

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

(R)-4-(Benzyloxymethyl)-2,2-dimethyl-1,3-dioxolane ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OCC(O1)COCC2=CC=CC=C2)C
• Isomeric SMILES: CC1(OC[C@H](O1)COCC2=CC=CC=C2)C

Technology Process of (R)-4-Benzyloxymethyl-2,2-dimethyl-1,3-dioxolane

There total 15 articles about (R)-4-Benzyloxymethyl-2,2-dimethyl-1,3-dioxolane 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: 99.0%

benzyl bromide (100-39-0) + 1,2-O-isopropylidene-D-glycerol (14347-78-5,36543-79-0) → (R)-2,2-dimethyl-4-benzoxymethyl-1,3-dioxolane (14347-83-2)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1002/chem.201204550

Reference yield: 80.0%

benzyl chloride (100-44-7) + 1,2-O-isopropylidene-D-glycerol (14347-78-5,36543-79-0) → (R)-2,2-dimethyl-4-benzoxymethyl-1,3-dioxolane (14347-83-2)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 12h; Ambient temperature;

DOI:10.1016/S0957-4166(97)00371-6

Reference yield:

benzyl bromide (100-39-0) + 2,3-O-isopropylidene glycerol (100-79-8,14347-78-5,22323-82-6,22323-83-7,36543-79-0) → 1-O-benzyl-2,3-O-isopropylidene glycerol (14347-83-2,15028-56-5,16495-03-7,76189-94-1)

Guidance literature:

With sodium hydride; Multistep reaction; 1.) DMF, 2.) DMF;

DOI:10.1016/S0040-4039(00)80790-X

upstream raw materials:

benzyl bromide

1,2-O-isopropylidene-D-glycerol

benzyl chloride

(S)-benzyl glycidyl ether

Downstream raw materials:

(4R)-4-(phenylmethoxymethyl)-1,3,2-dioxathiolane 2,2-dioxide

(S)-2-Benzyloxymethyl-cyclopropane-1,1-dicarboxylic acid diethyl ester

(1R,2S)-2-Benzyloxymethyl-cyclopropane-1,1-dicarboxylic acid ethyl ester

(1S,2S)-2-Benzyloxymethyl-1-tert-butoxycarbonylamino-cyclopropanecarboxylic acid ethyl ester

Refernces

• 1、 Cunha, Ana V.,Havenith, Remco W. A.,Holzheimer, Mira,Minnaard, Adriaan J.,Schouten, Stefan,Sinninghe Damsté, Jaap S.. "Total Synthesis of the Alleged Structure of Crenarchaeol Enables Structure Revision**". supporting information. p. 17504 - 17513. Retrieved 2021/07/06.
• 2、 Gudmundsson, Haraldur G.,Haraldsson, Gudmundur G.,Kallio, Heikki,Kalpio, Marika,Linderborg, Kaisa M.,Magnússon, Jóhann D.,Yang, Baoru. "Synthesis and enantiospecific analysis of enantiostructured triacylglycerols containing n-3 polyunsaturated fatty acids". . . Retrieved 2020/07/08.