(2R,3R,4S)-1-[(tert-butyldimethylsilyl)oxy]-4-[(4-methoxybenzyl)-oxy]pentane-2,3-diol

Base Information

Chemical Name:(2R,3R,4S)-1-[(tert-butyldimethylsilyl)oxy]-4-[(4-methoxybenzyl)-oxy]pentane-2,3-diol
CAS No.:1608473-16-0
Molecular Formula:C₁₉H₃₄O₅Si
Molecular Weight:370.561
Hs Code.:

Synonyms:(2R,3R,4S)-1-[(tert-butyldimethylsilyl)oxy]-4-[(4-methoxybenzyl)-oxy]pentane-2,3-diol

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Chemical Property of (2R,3R,4S)-1-[(tert-butyldimethylsilyl)oxy]-4-[(4-methoxybenzyl)-oxy]pentane-2,3-diol

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Technology Process of (2R,3R,4S)-1-[(tert-butyldimethylsilyl)oxy]-4-[(4-methoxybenzyl)-oxy]pentane-2,3-diol

There total 5 articles about (2R,3R,4S)-1-[(tert-butyldimethylsilyl)oxy]-4-[(4-methoxybenzyl)-oxy]pentane-2,3-diol 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: 93.0%

: 1608472-94-1
(2R,3R,4S)-4-[(4-methoxybenzyl)oxy]pentane-1,2,3-triol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1608473-16-0
(2R,3R,4S)-1-[(tert-butyldimethylsilyl)oxy]-4-[(4-methoxybenzyl)-oxy]pentane-2,3-diol

Guidance literature:: (2R,3R,4S)-4-[(4-methoxybenzyl)oxy]pentane-1,2,3-triol; With 1H-imidazole; In dichloromethane; at 0 ℃; for 0.25h; Inert atmosphere;

tert-butyldimethylsilyl chloride; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;
DOI:10.1002/ejoc.201301215

Reference yield:

: (-)-(2E)-(4S)-ethyl 4-(p-methoxybenzyl)oxy-2-pentenoate

: 1608473-16-0
(2R,3R,4S)-1-[(tert-butyldimethylsilyl)oxy]-4-[(4-methoxybenzyl)-oxy]pentane-2,3-diol

Guidance literature:: Multi-step reaction with 4 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 / 0.25 h / 0 °C / Inert atmosphere

4.2: 1 h / 0 °C / Inert atmosphere

With 1H-imidazole; titanium(IV) isopropylate; L-(+)-diisopropyl tartrate; diisobutylaluminium hydride; sodium hydroxide; In dichloromethane; water; tert-butyl alcohol; 2.1: |Sharpless Asymmetric Epoxidation / 2.2: |Sharpless Allylic Amination;
DOI:10.1002/ejoc.201301215

Reference yield:

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

: 1608473-16-0
(2R,3R,4S)-1-[(tert-butyldimethylsilyl)oxy]-4-[(4-methoxybenzyl)-oxy]pentane-2,3-diol

Guidance literature:: Multi-step reaction with 2 steps

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

2.1: 1H-imidazole / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

2.2: 1 h / 0 °C / Inert atmosphere

With 1H-imidazole; sodium hydroxide; In dichloromethane; water; tert-butyl alcohol;
DOI:10.1002/ejoc.201301215