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

Base Information

Chemical Name:(2R,3R,4S)-4-[(4-methoxybenzyl)oxy]pentane-1,2,3-triol
CAS No.:1608472-94-1
Molecular Formula:C₁₃H₂₀O₅
Molecular Weight:256.299
Hs Code.:

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

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

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

There total 7 articles about (2R,3R,4S)-4-[(4-methoxybenzyl)oxy]pentane-1,2,3-triol 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: 72.0%

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

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

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

Guidance literature:: With sodium hydroxide; In water; tert-butyl alcohol; at 70 ℃; for 15h; diastereoselective reaction; Inert atmosphere;
DOI:10.1002/ejoc.201301215

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 3 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

With 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:

: 122151-36-4
(S)-2-O-(4'-methoxybenzyl)propan-1,2-diol

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

Guidance literature:: Multi-step reaction with 4 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

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

With titanium(IV) isopropylate; oxalyl dichloride; L-(+)-diisopropyl tartrate; diisobutylaluminium hydride; sodium hydroxide; In dichloromethane; water; dimethyl sulfoxide; tert-butyl alcohol; 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