(S)-4-O-(4-methoxybenzyl)-1,2,4-butanetriol

Base Information

• Chemical Name: (S)-4-O-(4-methoxybenzyl)-1,2,4-butanetriol
• CAS No.: 193416-58-9
• Molecular Formula: C12H18O4
• Molecular Weight: 226.273
• DSSTox Substance ID: DTXSID70473560
• Nikkaji Number: J2.829.833A
• Wikidata: Q82303046
• Mol file: 193416-58-9.mol

Synonyms:(S)-4-O-(4-methoxybenzyl)-1,2,4-butanetriol;193416-58-9;SCHEMBL3423227;DTXSID70473560;YRHIJTKHDXQBLC-NSHDSACASA-N

Chemical Property of (S)-4-O-(4-methoxybenzyl)-1,2,4-butanetriol

Chemical Property:

• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 226.12050905
• Heavy Atom Count: 16
• Complexity: 166

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)COCCC(CO)O
• Isomeric SMILES: COC1=CC=C(C=C1)COCC[C@@H](CO)O

Technology Process of (S)-4-O-(4-methoxybenzyl)-1,2,4-butanetriol

There total 8 articles about (S)-4-O-(4-methoxybenzyl)-1,2,4-butanetriol 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: 97.0%

(4S)-4-(2-[(4-methoxybenzyl)oxy]ethyl)-2,2-dimethyl-1,3-dioxolane (195257-54-6) → (2S)-4-[(4-methoxybenzyl)oxy]butane-1,2-diol (193416-58-9)

Guidance literature:

With cerium(III) chloride heptahydrate; oxalic acid; In acetonitrile; at 20 ℃; for 1.5h;

DOI:10.1055/s-0029-1218836

Reference yield: 90.0%

(S)-2,2-diethyl-4-(2-(4-methoxybenzyloxy)ethyl)-1,3-dioxolane (1460293-40-6) → (2S)-4-[(4-methoxybenzyl)oxy]butane-1,2-diol (193416-58-9)

Guidance literature:

(S)-2,2-diethyl-4-(2-(4-methoxybenzyloxy)ethyl)-1,3-dioxolane; With toluene-4-sulfonic acid; In methanol; at 20 ℃; for 5h;

With water; In methanol; at 20 ℃; for 4h;

DOI:10.1039/c3ob41569d

Reference yield: 78.0%

4-((4-methoxybenzyl)oxy)butanal (119649-27-3) → (2S)-4-[(4-methoxybenzyl)oxy]butane-1,2-diol (193416-58-9)

Guidance literature:

4-((4-methoxybenzyl)oxy)butanal; With Nitrosobenzene; D-Prolin; In dimethyl sulfoxide; at 20 ℃; for 1h; Inert atmosphere;

With sodium tetrahydroborate; In methanol; at 0 - 20 ℃; for 0.5h; Inert atmosphere;

With copper(ll) sulfate pentahydrate; In methanol; at 20 ℃; for 10h; regioselective reaction; Inert atmosphere;

DOI:10.1002/ejoc.201600625

upstream raw materials:

(4S)-4-(2-[(4-methoxybenzyl)oxy]ethyl)-2,2-dimethyl-1,3-dioxolane

4-(p-methoxybenzyloxy)-1,2-epoxybutane

p-Methoxybenzyl bromide

1-(4-methoxybenzyloxy)-3-butene

Downstream raw materials:

Methanesulfonic acid (S)-2-hydroxy-4-(4-methoxy-benzyloxy)-butyl ester

(S)-(1-(1,3-dithian-2-yl)-4-(4-methoxybenzyloxy)butan-2-yloxy)(tert-butyl)dimethylsilane

(S)-2-(4-((4-methoxybenzyl)oxy)-2-(methoxymethoxy)butyl)-1,3-dithiane

C₁₆H₂₄O₃S₂

Refernces

• 1、 Sudina, Purushotham Reddy,Motati, Damoder Reddy,Seema, Aravind. "Stereocontrolled Total Synthesis of Nonenolide". . p. 1399 - 1404. Retrieved 2018/06/29.
• 2、 Pfeiffer, Bernhard,Speck-Gisler, Sandra,Barandun, Luzi,Senft, Ursula,De Groot, Claire,Lehmann, Irene,Ganci, Walter,Gertsch, Juerg,Altmann, Karl-Heinz. "Total synthesis and configurational assignment of the marine natural product haliclamide". . p. 2553 - 2563. Retrieved 2013/05/22.