((2S,3R,4S)-3-(benzyloxy)-4-(benzyloxymethyl)-1-nonylazetidin-2-yl)methanol

Base Information

• Chemical Name: ((2S,3R,4S)-3-(benzyloxy)-4-(benzyloxymethyl)-1-nonylazetidin-2-yl)methanol
• CAS No.: 1366423-20-2
• Molecular Formula: C₂₈H₄₁NO₃
• Molecular Weight: 439.638

Synonyms:((2S,3R,4S)-3-(benzyloxy)-4-(benzyloxymethyl)-1-nonylazetidin-2-yl)methanol

Chemical Property of ((2S,3R,4S)-3-(benzyloxy)-4-(benzyloxymethyl)-1-nonylazetidin-2-yl)methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of ((2S,3R,4S)-3-(benzyloxy)-4-(benzyloxymethyl)-1-nonylazetidin-2-yl)methanol

There total 11 articles about ((2S,3R,4S)-3-(benzyloxy)-4-(benzyloxymethyl)-1-nonylazetidin-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: 76.0%

caprinaldehyde (112-31-2) + (2S,3S,4S)-3-(benzyloxy)-2-(benzyloxymethyl)-4-((tert-butyldimethylsilyloxy)methyl)azetidine (1366422-92-5) → ((2S,3R,4S)-3-(benzyloxy)-4-(benzyloxymethyl)-1-nonylazetidin-2-yl)methanol (1366423-20-2)

Guidance literature:

caprinaldehyde; (2S,3S,4S)-3-(benzyloxy)-2-(benzyloxymethyl)-4-((tert-butyldimethylsilyloxy)methyl)azetidine; With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20 ℃; for 16h; Inert atmosphere;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1021/jo202054g

Reference yield:

(R)-4-((2S,3R)-3-((benzyloxy)methyl)oxiran-2-yl)-2,2-dimethyl-1,3-dioxolane (221216-43-9) → ((2S,3R,4S)-3-(benzyloxy)-4-(benzyloxymethyl)-1-nonylazetidin-2-yl)methanol (1366423-20-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: sodium azide; water; ammonium chloride / ethyl methyl ether / Reflux

2.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran; mineral oil / 1 h / 20 °C / Inert atmosphere

3.1: lithium aluminium tetrahydride / tetrahydrofuran / -78 - 0 °C / Inert atmosphere

4.1: triethylamine / dichloromethane / 4 h / 20 °C / Inert atmosphere

5.1: hydrogenchloride; water / methanol / 40 °C

6.1: dmap; triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

7.1: di-isopropyl azodicarboxylate; triphenylphosphine / dichloromethane / 0 - 20 °C / Inert atmosphere

8.1: naphthalene; sodium / 1,2-dimethoxyethane / -60 °C / Inert atmosphere

9.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 16 h / 20 °C / Inert atmosphere

9.2: 4 h / 20 °C / Inert atmosphere

With hydrogenchloride; dmap; lithium aluminium tetrahydride; sodium azide; naphthalene; di-isopropyl azodicarboxylate; water; sodium; tetra-(n-butyl)ammonium iodide; sodium tris(acetoxy)borohydride; sodium hydride; ammonium chloride; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethyl methyl ether; dichloromethane; 1,2-dichloro-ethane; mineral oil; 7.1: Mitsunobu reaction;

DOI:10.1021/jo202054g

Reference yield:

benzyl bromide (100-39-0) → ((2S,3R,4S)-3-(benzyloxy)-4-(benzyloxymethyl)-1-nonylazetidin-2-yl)methanol (1366423-20-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran; mineral oil / 1 h / 20 °C / Inert atmosphere

2.1: lithium aluminium tetrahydride / tetrahydrofuran / -78 - 0 °C / Inert atmosphere

3.1: triethylamine / dichloromethane / 4 h / 20 °C / Inert atmosphere

4.1: hydrogenchloride; water / methanol / 40 °C

5.1: dmap; triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

6.1: di-isopropyl azodicarboxylate; triphenylphosphine / dichloromethane / 0 - 20 °C / Inert atmosphere

7.1: naphthalene; sodium / 1,2-dimethoxyethane / -60 °C / Inert atmosphere

8.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 16 h / 20 °C / Inert atmosphere

8.2: 4 h / 20 °C / Inert atmosphere

With hydrogenchloride; dmap; lithium aluminium tetrahydride; naphthalene; di-isopropyl azodicarboxylate; water; sodium; tetra-(n-butyl)ammonium iodide; sodium tris(acetoxy)borohydride; sodium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; 1,2-dichloro-ethane; mineral oil; 6.1: Mitsunobu reaction;

DOI:10.1021/jo202054g

upstream raw materials:

(R)-4-((2S,3R)-3-((benzyloxy)methyl)oxiran-2-yl)-2,2-dimethyl-1,3-dioxolane

caprinaldehyde

(2S,3S,4S)-3-(benzyloxy)-2-(benzyloxymethyl)-4-((tert-butyldimethylsilyloxy)methyl)azetidine

benzyl bromide

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