(S)-4-BENZYLOXYMETHYL-2,2-DIMETHYL-1,3-DIOXOLANE

Base Information

• Chemical Name: (S)-4-BENZYLOXYMETHYL-2,2-DIMETHYL-1,3-DIOXOLANE
• CAS No.: 16495-03-7
• Molecular Formula: C13H18O3
• Molecular Weight: 222.284
• Hs Code.: 2932999099
• Mol file: 16495-03-7.mol

Synonyms:1,3-Dioxolane,2,2-dimethyl-4-[(phenylmethoxy)methyl]-, (S)-;1,3-Dioxolane,4-[(benzyloxy)methyl]-2,2-dimethyl-, (S)- (8CI);1,2-Isopropylidene-3-O-benzyl-sn-glycerol;

Chemical Property of (S)-4-BENZYLOXYMETHYL-2,2-DIMETHYL-1,3-DIOXOLANE

Chemical Property:

• Appearance/Colour: clear yellow oil
• Refractive Index: n20/D 1.496
• Boiling Point: 300.3 °C at 760 mmHg
• Flash Point: 100 °C
• PSA: 27.69000
• Density: 1.039 g/cm³
• LogP: 2.35470
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Ethyl Acetate

Purity/Quality:

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

(S)-1-Benzyl-2,3-O-isopropylideneGlycerol ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

Useful:

• Uses: (S)-4-BENZYLOXYMETHYL-2,2-DIMETHYL-1,3-DIOXOLANE is used in the preparation of the analogs of dioxolanes Dexoxadrol and Etoxadrol as potential phencyclidine-like agents.

Technology Process of (S)-4-BENZYLOXYMETHYL-2,2-DIMETHYL-1,3-DIOXOLANE

There total 25 articles about (S)-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: 100.0%

(S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol (22323-82-6,36543-79-0) + benzyl chloride (100-44-7) → (S)-4-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolane (16495-03-7)

Guidance literature:

With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 0 - 20 ℃; for 4h;

Reference yield: 100.0%

(S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol (22323-82-6,36543-79-0) + benzyl bromide (100-39-0) → (S)-4-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolane (16495-03-7)

Guidance literature:

With potassium hydroxide; 18-crown-6 ether; In tetrahydrofuran; at 20 ℃;

DOI:10.1248/cpb.47.1659

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:

(S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol

(R)-3-benzyloxy-1,2-propanediol

2,2-dimethoxy-propane

benzyl bromide

Downstream raw materials:

(R)-3-benzyloxy-1,2-propanediol

(2S)-3-(benzyloxy)propane-1,2-diol

(S)-1-(benzyloxy)-3-trityloxypropan-2-ol

Octanedioic acid allyl ester (S)-1-benzyloxymethyl-2-trityloxy-ethyl ester

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、 Gan, Chin Heng,Hua, Kuo-Feng,Lam, Yulin,Li, Lan-Hui,Peng, Yi-Jen,Wei, Chih-Feng,Wijaya, Hadhi,Wu, Shih-Hsiung. "H-Phosphonate Synthesis and Biological Evaluation of an Immunomodulatory Phosphoglycolipid from Thermophilic Bacteria". . . Retrieved 2020/04/02.