(2S,3S)-3-(4-(benzyloxy)-3-methoxyphenyl)-2,3-dihydroxypropyl 4-methylbenzenesulfonate

Base Information

• Chemical Name: (2S,3S)-3-(4-(benzyloxy)-3-methoxyphenyl)-2,3-dihydroxypropyl 4-methylbenzenesulfonate
• CAS No.: 1240326-75-3
• Molecular Formula: C₂₄H₂₆O₇S
• Molecular Weight: 458.532
• Mol file: 1240326-75-3.mol

Synonyms:(2S,3S)-3-(4-(benzyloxy)-3-methoxyphenyl)-2,3-dihydroxypropyl 4-methylbenzenesulfonate

Chemical Property of (2S,3S)-3-(4-(benzyloxy)-3-methoxyphenyl)-2,3-dihydroxypropyl 4-methylbenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-3-(4-(benzyloxy)-3-methoxyphenyl)-2,3-dihydroxypropyl 4-methylbenzenesulfonate

There total 6 articles about (2S,3S)-3-(4-(benzyloxy)-3-methoxyphenyl)-2,3-dihydroxypropyl 4-methylbenzenesulfonate 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: 83.0%

p-toluenesulfonyl chloride (98-59-9) + (1S,2S)-1-(4-benzyloxy-3-methoxyphenyl)-2,3-dihydroxypropanol (213595-71-2) → (2S,3S)-3-(4-(benzyloxy)-3-methoxyphenyl)-2,3-dihydroxypropyl 4-methylbenzenesulfonate (1240326-75-3)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; optical yield given as %de;

DOI:10.3906/kim-0908-201

Reference yield:

(E)-3-(4-benzyloxy-3-methoxyphenyl)acrylic acid ethyl ester (38157-08-3) → (2S,3S)-3-(4-(benzyloxy)-3-methoxyphenyl)-2,3-dihydroxypropyl 4-methylbenzenesulfonate (1240326-75-3)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium aluminium tetrahydride; aluminum (III) chloride / tetrahydrofuran

2: ; methanesulfonamide; water; tert-butyl alcohol / 0 °C

3: pyridine / dichloromethane / 20 °C

With pyridine; aluminum (III) chloride; lithium aluminium tetrahydride; methanesulfonamide; water; tert-butyl alcohol; In tetrahydrofuran; dichloromethane; 2: Sharpless dihydroxylation;

DOI:10.1016/j.mencom.2010.05.009

Reference yield:

(2E)-3-(4-O-benzyloxy-3-methoxyphenyl)prop-2-en-1-ol (38153-27-4) → (2S,3S)-3-(4-(benzyloxy)-3-methoxyphenyl)-2,3-dihydroxypropyl 4-methylbenzenesulfonate (1240326-75-3)

Guidance literature:

Multi-step reaction with 2 steps

1: ; methanesulfonamide; water; tert-butyl alcohol / 0 °C

2: pyridine / dichloromethane / 20 °C

With pyridine; methanesulfonamide; water; tert-butyl alcohol; In dichloromethane; 1: Sharpless dihydroxylation;

DOI:10.1016/j.mencom.2010.05.009

upstream raw materials:

p-toluenesulfonyl chloride

(1S,2S)-1-(4-benzyloxy-3-methoxyphenyl)-2,3-dihydroxypropanol

3-methoxy-4-(phenylmethoxy)benzaldehyde

(2E)-3-(4-O-benzyloxy-3-methoxyphenyl)prop-2-en-1-ol

Downstream raw materials:

(1S,2S)-1-(4-(benzyloxy)-3-methoxyphenyl)-2,3-epoxypropan-1-ol

(1S,2S)-1-(4-(benzyloxy)-3-methoxyphenyl)-1-(tetrahydro-2H-pyran-2-yloxy)propan-2-ol

erythro-(7S,8R)-7-(4-hydroxy-3-methoxypheny1)-8-[(2'-methoxy-4'-(E)-propenyl)phenoxy]propan-7-ol

(1S,2S)-1-(3-methoxy-4-(methoxymethoxy)phenyl)-1-(tetrahydro-2H-pyran-2-yloxy)propan-2-ol