(4S)-3-benzyl-4-[(1'R,2'R,3'E)-1',2'-bis(benzyloxy)hexadec-3'-en-1'-yl]oxazolidin-2-one

Base Information

• Chemical Name: (4S)-3-benzyl-4-[(1'R,2'R,3'E)-1',2'-bis(benzyloxy)hexadec-3'-en-1'-yl]oxazolidin-2-one
• CAS No.: 1611460-23-1
• Molecular Formula: C₄₀H₅₃NO₄
• Molecular Weight: 611.865
• Mol file: 1611460-23-1.mol

Synonyms:(4S)-3-benzyl-4-[(1'R,2'R,3'E)-1',2'-bis(benzyloxy)hexadec-3'-en-1'-yl]oxazolidin-2-one

Chemical Property of (4S)-3-benzyl-4-[(1'R,2'R,3'E)-1',2'-bis(benzyloxy)hexadec-3'-en-1'-yl]oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-3-benzyl-4-[(1'R,2'R,3'E)-1',2'-bis(benzyloxy)hexadec-3'-en-1'-yl]oxazolidin-2-one

There total 24 articles about (4S)-3-benzyl-4-[(1'R,2'R,3'E)-1',2'-bis(benzyloxy)hexadec-3'-en-1'-yl]oxazolidin-2-one 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:

C27H27NO5 + n-tridecyltriphenylphosphonium bromide (13266-02-9) → (4S)-3-benzyl-4-[(1'R,2'R,3'E)-1',2'-bis(benzyloxy)hexadec-3'-en-1'-yl]oxazolidin-2-one (1611460-23-1) + (4S)-3-benzyl-4-[(1'R,2'R,3'Z)-1',2'-bis(benzyloxy)hexadec-3'-en-1'-yl]oxazolidin-2-one (1611460-22-0)

Guidance literature:

n-tridecyltriphenylphosphonium bromide; With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; at 20 ℃; for 0.0833333h; Inert atmosphere;

C₂₇H₂₇NO₅; In tetrahydrofuran; hexane; at 20 ℃; for 0.416667h; Overall yield = 83 %; Overall yield = 0.4 g; diastereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tetasy.2014.04.002

Reference yield:

C18H18O5 (1611459-82-5) → (4S)-3-benzyl-4-[(1'R,2'R,3'E)-1',2'-bis(benzyloxy)hexadec-3'-en-1'-yl]oxazolidin-2-one (1611460-23-1) + (4S)-3-benzyl-4-[(1'R,2'R,3'Z)-1',2'-bis(benzyloxy)hexadec-3'-en-1'-yl]oxazolidin-2-one (1611460-22-0)

Guidance literature:

Multi-step reaction with 15 steps

1.1: sodium tetrahydroborate / methanol; dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

2.1: toluene-4-sulfonic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere

3.1: potassium carbonate; methanol / 4.42 h / 0 - 20 °C / Inert atmosphere

4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 1 h / Inert atmosphere; Reflux

5.1: sodium hydride / mineral oil; tetrahydrofuran / 0.42 h / -10 - 0 °C / Inert atmosphere

5.2: 1.5 h / 0 °C / Inert atmosphere

6.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -50 - -30 °C / Inert atmosphere

7.1: sodium hydride / mineral oil; tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

7.2: 0.5 h / 0 °C / Inert atmosphere

8.1: potassium carbonate / o-xylene / 1.5 h / 150 °C / Sealed tube; Inert atmosphere; Microwave irradiation

9.1: ozone / methanol; dichloromethane / 0.25 h / -78 °C

9.2: 0.1 h / -78 - 20 °C / Inert atmosphere

10.1: toluene-4-sulfonic acid / methanol / 1.5 h / 20 °C / Inert atmosphere

11.1: dmap; pyridine / 22 h / 60 °C / Inert atmosphere

12.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 °C / Inert atmosphere

12.2: 0.5 h / 0 - 20 °C / Inert atmosphere

13.1: toluene-4-sulfonic acid / methanol; dichloromethane / 3.5 h / 20 °C / Inert atmosphere

14.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 0.5 h / 20 °C / Inert atmosphere; Reflux

15.1: n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane / hexane; tetrahydrofuran / 0.08 h / 20 °C / Inert atmosphere

15.2: 0.42 h / 20 °C / Inert atmosphere

With pyridine; methanol; dmap; sodium tetrahydroborate; n-butyllithium; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; ozone; 1,1,1,3,3,3-hexamethyl-disilazane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; hexane; dichloromethane; o-xylene; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil; 5.1: |Horner-Wadsworth-Emmons Olefination / 8.1: |Overman Rearrangement;

DOI:10.1016/j.tetasy.2014.04.002

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose (34370-91-7,59358-33-7,68354-70-1,70798-12-8,19139-80-1) → (4S)-3-benzyl-4-[(1'R,2'R,3'E)-1',2'-bis(benzyloxy)hexadec-3'-en-1'-yl]oxazolidin-2-one (1611460-23-1) + (4S)-3-benzyl-4-[(1'R,2'R,3'Z)-1',2'-bis(benzyloxy)hexadec-3'-en-1'-yl]oxazolidin-2-one (1611460-22-0)

Guidance literature:

Multi-step reaction with 18 steps

1.1: dmap; pyridine / 1.67 h / 0 - 20 °C / Inert atmosphere

2.1: trifluoroacetic acid / water / 6 h / 0 °C / Inert atmosphere

3.1: sodium periodate / methanol; water / 1 h / 20 °C / Inert atmosphere

4.1: sodium tetrahydroborate / methanol; dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

5.1: toluene-4-sulfonic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere

6.1: potassium carbonate; methanol / 4.42 h / 0 - 20 °C / Inert atmosphere

7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 1 h / Inert atmosphere; Reflux

8.1: sodium hydride / mineral oil; tetrahydrofuran / 0.42 h / -10 - 0 °C / Inert atmosphere

8.2: 1.5 h / 0 °C / Inert atmosphere

9.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -50 - -30 °C / Inert atmosphere

10.1: sodium hydride / mineral oil; tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

10.2: 0.5 h / 0 °C / Inert atmosphere

11.1: potassium carbonate / o-xylene / 1.5 h / 150 °C / Sealed tube; Inert atmosphere; Microwave irradiation

12.1: ozone / methanol; dichloromethane / 0.25 h / -78 °C

12.2: 0.1 h / -78 - 20 °C / Inert atmosphere

13.1: toluene-4-sulfonic acid / methanol / 1.5 h / 20 °C / Inert atmosphere

14.1: dmap; pyridine / 22 h / 60 °C / Inert atmosphere

15.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 °C / Inert atmosphere

15.2: 0.5 h / 0 - 20 °C / Inert atmosphere

16.1: toluene-4-sulfonic acid / methanol; dichloromethane / 3.5 h / 20 °C / Inert atmosphere

17.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 0.5 h / 20 °C / Inert atmosphere; Reflux

18.1: n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane / hexane; tetrahydrofuran / 0.08 h / 20 °C / Inert atmosphere

18.2: 0.42 h / 20 °C / Inert atmosphere

With pyridine; methanol; dmap; sodium tetrahydroborate; sodium periodate; n-butyllithium; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; ozone; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; hexane; dichloromethane; o-xylene; water; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil; 8.1: |Horner-Wadsworth-Emmons Olefination / 11.1: |Overman Rearrangement;

DOI:10.1016/j.tetasy.2014.04.002

upstream raw materials:

(4S)-3-benzyl-4-[(1'R,2'R)-1',2'-bis(benzyloxy)-3'-hydroxypropyl]oxazolidin-2-one

C₁₈H₁₈O₅

ethyl (Z)-3-[(4'R,5'R)-5'-(benzyloxy)-2',2'-dimethyl-1',3'-dioxan-4'-yl]acrylate

C₁₄H₁₈O₄