(2S,3S,4r,Z)-2-(benzylamino)octadec-5-ene-1,3,4-triol

Base Information

• Chemical Name: (2S,3S,4r,Z)-2-(benzylamino)octadec-5-ene-1,3,4-triol
• CAS No.: 1332640-41-1
• Molecular Formula: C₂₅H₄₃NO₃
• Molecular Weight: 405.621
• Mol file: 1332640-41-1.mol

Synonyms:(2S,3S,4r,Z)-2-(benzylamino)octadec-5-ene-1,3,4-triol

Chemical Property of (2S,3S,4r,Z)-2-(benzylamino)octadec-5-ene-1,3,4-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4r,Z)-2-(benzylamino)octadec-5-ene-1,3,4-triol

There total 10 articles about (2S,3S,4r,Z)-2-(benzylamino)octadec-5-ene-1,3,4-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: 94.0%

(S)-3-benzyl-4-((4S,5R)-2,2-dimethyl-5-((Z)-tetradec-1-enyl)-1,3-dioxolan-4-yl)oxa-zolidin-2-one (1332640-40-0) → (2S,3S,4r,Z)-2-(benzylamino)octadec-5-ene-1,3,4-triol (1332640-41-1)

Guidance literature:

(S)-3-benzyl-4-((4S,5R)-2,2-dimethyl-5-((Z)-tetradec-1-enyl)-1,3-dioxolan-4-yl)oxa-zolidin-2-one; With hydrogenchloride; water; In methanol; for 6h; Reflux;

With sodium hydroxide; In methanol; water;

DOI:10.1016/j.tetlet.2011.07.032

Reference yield:

C21H35NO4Si (1233851-77-8) → (2S,3S,4r,Z)-2-(benzylamino)octadec-5-ene-1,3,4-triol (1332640-41-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: magnesium / tetrahydrofuran

1.2: 2 h / -78 - 20 °C / Inert atmosphere

1.3: Inert atmosphere

2.1: sodium hydrogencarbonate / methanol / 1 h / 0 - 20 °C

3.1: ozone / dichloromethane / 0.5 h / -78 °C

3.2: 0.5 h / -78 °C

4.1: sodium tetrahydroborate / methanol / 2 h / 0 °C

5.1: sodium hydride / tetrahydrofuran; wax / 0.5 h / 0 °C / Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C

7.1: sodium periodate; sodium hydrogencarbonate / methanol; water / 2 h / 0 °C

8.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -40 °C / Inert atmosphere

8.2: 0.5 h / -40 °C / Inert atmosphere

9.1: hydrogenchloride; water / methanol / 6 h / Reflux

With hydrogenchloride; sodium tetrahydroborate; sodium periodate; n-butyllithium; tetrabutyl ammonium fluoride; water; sodium hydride; sodium hydrogencarbonate; ozone; magnesium; In tetrahydrofuran; methanol; wax; hexane; dichloromethane; water; 8.2: Wittig reaction;

DOI:10.1016/j.tetlet.2011.07.032

Reference yield:

benzyl benzyl((S)-1-((4S,5R)-5-((R)-2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl)carbamate (1332640-36-4) → (2S,3S,4r,Z)-2-(benzylamino)octadec-5-ene-1,3,4-triol (1332640-41-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydride / tetrahydrofuran; wax / 0.5 h / 0 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C

3.1: sodium periodate; sodium hydrogencarbonate / methanol; water / 2 h / 0 °C

4.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -40 °C / Inert atmosphere

4.2: 0.5 h / -40 °C / Inert atmosphere

5.1: hydrogenchloride; water / methanol / 6 h / Reflux

With hydrogenchloride; sodium periodate; n-butyllithium; tetrabutyl ammonium fluoride; water; sodium hydride; sodium hydrogencarbonate; In tetrahydrofuran; methanol; wax; hexane; water; 4.2: Wittig reaction;

DOI:10.1016/j.tetlet.2011.07.032

upstream raw materials:

C₂₁H₃₅NO₄Si

benzyl benzyl((S)-1-((4S,5R)-5-((R)-2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)allyl)carbamate

benzyl benzyl((S)-1-((4S,5R)-5-((R)-2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl)carbamate

3-benzyl-4-((4S,5R)-5-((R)-2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)oxazolidin-2-one

Downstream raw materials:

D-ribo-phytosphingosine

tert-butyl [(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]carbamate