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

Base Information

• Chemical Name: (2R,3S,4S)-2,3-bis[(tert-butyldimethylsilyl)oxy]-4-[(4-methoxybenzyl)oxy]pentan-1-ol
• CAS No.: 1608472-96-3
• Molecular Formula: C₂₅H₄₈O₅Si₂
• Molecular Weight: 484.824
• Mol file: 1608472-96-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about (2R,3S,4S)-2,3-bis[(tert-butyldimethylsilyl)oxy]-4-[(4-methoxybenzyl)oxy]pentan-1-ol 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: 85.0%

(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 (1608472-95-2) → (2R,3S,4S)-2,3-bis[(tert-butyldimethylsilyl)oxy]-4-[(4-methoxybenzyl)oxy]pentan-1-ol (1608472-96-3)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at -15 ℃; for 0.5h; regioselective reaction; Inert atmosphere;

DOI:10.1002/ejoc.201301215

Reference yield:

((2S,3S)-3-{(S)-1-[(4-methoxybenzyl)oxy]ethyl}oxiran-2-yl)methanol (1608472-93-0) → (2R,3S,4S)-2,3-bis[(tert-butyldimethylsilyl)oxy]-4-[(4-methoxybenzyl)oxy]pentan-1-ol (1608472-96-3)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydroxide / water; tert-butyl alcohol / 15 h / 70 °C / Inert atmosphere

2: 1H-imidazole / dichloromethane; N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

3: toluene-4-sulfonic acid / methanol / 0.5 h / -15 °C / Inert atmosphere

With 1H-imidazole; toluene-4-sulfonic acid; sodium hydroxide; In methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1002/ejoc.201301215

Reference yield:

(-)-(2E)-(4S)-ethyl 4-(p-methoxybenzyl)oxy-2-pentenoate → (2R,3S,4S)-2,3-bis[(tert-butyldimethylsilyl)oxy]-4-[(4-methoxybenzyl)oxy]pentan-1-ol (1608472-96-3)

Guidance literature:

Multi-step reaction with 5 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

3.1: sodium hydroxide / water; tert-butyl alcohol / 15 h / 70 °C / Inert atmosphere

4.1: 1H-imidazole / dichloromethane; N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

5.1: toluene-4-sulfonic acid / methanol / 0.5 h / -15 °C / Inert atmosphere

With 1H-imidazole; titanium(IV) isopropylate; L-(+)-diisopropyl tartrate; diisobutylaluminium hydride; toluene-4-sulfonic acid; sodium hydroxide; In methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 2.1: |Sharpless Asymmetric Epoxidation / 2.2: |Sharpless Allylic Amination;

DOI:10.1002/ejoc.201301215

upstream raw materials:

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

(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

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

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

Downstream raw materials:

(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

C₂₅H₄₆O₅Si₂

(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-yl acetate