((2S,3S)-3-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}oxiran-2-yl)methanol

Base Information

• Chemical Name: ((2S,3S)-3-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}oxiran-2-yl)methanol
• CAS No.: 1608472-93-0
• Molecular Formula: C₁₃H₁₈O₄
• Molecular Weight: 238.284
• Mol file: 1608472-93-0.mol

Synonyms:((2S,3S)-3-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}oxiran-2-yl)methanol

Chemical Property of ((2S,3S)-3-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}oxiran-2-yl)methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((2S,3S)-3-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}oxiran-2-yl)methanol

There total 3 articles about ((2S,3S)-3-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}oxiran-2-yl)methanol 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: 91.0%

(S,E)-4-[(4-methoxybenzyl)oxy]pent-2-en-1-ol (1262205-99-1) → ((2S,3S)-3-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}oxiran-2-yl)methanol (1608472-93-0)

Guidance literature:

(S,E)-4-[(4-methoxybenzyl)oxy]pent-2-en-1-ol; With titanium(IV) isopropylate; L-(+)-diisopropyl tartrate; In dichloromethane; at -20 ℃; for 0.5h; Inert atmosphere; Molecular sieve;

With tert.-butylhydroperoxide; In dichloromethane; toluene; for 8h; Optical yield = 94 %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1002/ejoc.201301215

Reference yield:

(-)-(2E)-(4S)-ethyl 4-(p-methoxybenzyl)oxy-2-pentenoate → ((2S,3S)-3-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}oxiran-2-yl)methanol (1608472-93-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: diisobutylaluminium hydride / dichloromethane / 1 h / 0 °C / Inert atmosphere

2.1: titanium(IV) isopropylate; L-(+)-diisopropyl tartrate / dichloromethane / 0.5 h / -20 °C / Inert atmosphere; Molecular sieve

2.2: 8 h / Inert atmosphere

With titanium(IV) isopropylate; L-(+)-diisopropyl tartrate; diisobutylaluminium hydride; In dichloromethane; 2.1: |Sharpless Asymmetric Epoxidation / 2.2: |Sharpless Allylic Amination;

DOI:10.1002/ejoc.201301215

Reference yield:

(S)-2-O-(4'-methoxybenzyl)propan-1,2-diol (122151-36-4) → ((2S,3S)-3-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}oxiran-2-yl)methanol (1608472-93-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 0.5 h / -78 °C / Inert atmosphere

1.2: 0.5 h / -78 °C / Inert atmosphere

1.3: 4 h / -78 - 20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / dichloromethane / 1 h / 0 °C / Inert atmosphere

3.1: titanium(IV) isopropylate; L-(+)-diisopropyl tartrate / dichloromethane / 0.5 h / -20 °C / Inert atmosphere; Molecular sieve

3.2: 8 h / Inert atmosphere

With titanium(IV) isopropylate; oxalyl dichloride; L-(+)-diisopropyl tartrate; diisobutylaluminium hydride; In dichloromethane; dimethyl sulfoxide; 1.1: |Wittig Olefination / 1.2: |Wittig Olefination / 1.3: |Wittig Olefination / 3.1: |Sharpless Asymmetric Epoxidation / 3.2: |Sharpless Allylic Amination;

DOI:10.1002/ejoc.201301215

upstream raw materials:

(S)-2-O-(4'-methoxybenzyl)propan-1,2-diol

(S,E)-4-[(4-methoxybenzyl)oxy]pent-2-en-1-ol

Downstream raw materials:

(2R,3R,4S)-4-[(4-methoxybenzyl)oxy]pentane-1,2,3-triol

(5S,6R)-6-[(tert-butyldimethylsilyl)oxy]-5-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,9,9,10,10-octamethyl-4,8-dioxa-3,9-disilaundecane

(2R,3S,4S)-2,3-bis[(tert-butyldimethylsilyl)oxy]-4-[(4-methoxybenzyl)oxy]pentan-1-ol

(5S,6R,7R)-6-[(tert-butyldimethylsilyl)oxy]-5-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,12,12,13,13-octamethyl-4,11-dioxa-3,12-disilatetradec-8-yn-7-ol