(2R,3S)-3-hydroxy-1,2-O-isopropylidene-3-p-methoxyphenyl-1,2-propanediol

Base Information

• Chemical Name: (2R,3S)-3-hydroxy-1,2-O-isopropylidene-3-p-methoxyphenyl-1,2-propanediol
• CAS No.: 106363-66-0
• Molecular Formula: C₁₃H₁₈O₄
• Molecular Weight: 238.284
• Mol file: 106363-66-0.mol

Synonyms:(2R,3S)-3-hydroxy-1,2-O-isopropylidene-3-p-methoxyphenyl-1,2-propanediol

Chemical Property of (2R,3S)-3-hydroxy-1,2-O-isopropylidene-3-p-methoxyphenyl-1,2-propanediol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-3-hydroxy-1,2-O-isopropylidene-3-p-methoxyphenyl-1,2-propanediol

There total 3 articles about (2R,3S)-3-hydroxy-1,2-O-isopropylidene-3-p-methoxyphenyl-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: 80.0%

4-methoxyphenyl magnesium bromide (13139-86-1) + 2,3-isopropylidene-glyceraldehyde (15186-48-8) → (2R,3R)-3-hydroxy-1,2-O-isopropylidene-3-p-methoxyphenyl-1,2-propanediol (102389-96-8) + (2R,3S)-3-hydroxy-1,2-O-isopropylidene-3-p-methoxyphenyl-1,2-propanediol (106363-66-0)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1081/CAR-200030048

Reference yield:

((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-(4-methoxy-phenyl)-methanone → (2R,3R)-3-hydroxy-1,2-O-isopropylidene-3-p-methoxyphenyl-1,2-propanediol (102389-96-8) + (2R,3S)-3-hydroxy-1,2-O-isopropylidene-3-p-methoxyphenyl-1,2-propanediol (106363-66-0)

Guidance literature:

With L-Selectride; In tetrahydrofuran; at -78 ℃; for 3h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1246/bcsj.62.2121

Reference yield:

1,2:5,6-di-O-isopropylidene-D-mannitol (1707-77-3) → (2R,3S)-3-hydroxy-1,2-O-isopropylidene-3-p-methoxyphenyl-1,2-propanediol (106363-66-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / sodium periodate; sodium hydrogen carbonate / CH₂Cl₂; H₂O / 3 h

2: 80 percent / tetrahydrofuran / 3 h / 20 °C

With sodium periodate; sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane; water; 2: Grignard reaction;

DOI:10.1081/CAR-200030048

upstream raw materials:

4-methoxyphenyl magnesium bromide

2,3-isopropylidene-glyceraldehyde

1,2:5,6-di-O-isopropylidene-D-mannitol

Downstream raw materials:

(2S,3R)-3-azido-1,2-O-isopropylidene-3-p-methoxyphenyl-1,2-propanediol

(2S,3R)-3-amino-1,2-O-isopropylidene-3-p-methoxyphenyl-1,2-propanediol

(2S,3R)-3-tert-butoxycarbonylamino-1,2-O-isopropylidene-3-p-methoxyphenyl-1,2-propanediol

(2S,3R)-3-tert-butoxycarbonylamino-1,2-O-isopropylidene-3-p-methoxyphenyl-1,2-propanediol