(2S,3R,4E)-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}hex-4-en-1,2-diol

Base Information

• Chemical Name: (2S,3R,4E)-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}hex-4-en-1,2-diol
• CAS No.: 1606140-55-9
• Molecular Formula: C₂₁H₂₇NO₂
• Molecular Weight: 325.451
• Mol file: 1606140-55-9.mol

Synonyms:(2S,3R,4E)-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}hex-4-en-1,2-diol

Chemical Property of (2S,3R,4E)-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}hex-4-en-1,2-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4E)-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}hex-4-en-1,2-diol

There total 5 articles about (2S,3R,4E)-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}hex-4-en-1,2-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: 75.0%

tert-butyl (2S,3R,4E)-2-hydroxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}hex-4-enoate (1606140-53-7) → (2S,3R,4E)-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}hex-4-en-1,2-diol (1606140-55-9)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃; for 16h; Inert atmosphere;

DOI:10.1016/j.tet.2014.03.055

Reference yield:

sorbic Acid (110-44-1,91751-55-2) → (2S,3R,4E)-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}hex-4-en-1,2-diol (1606140-55-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: water; sulfuric acid / dichloromethane / 0 - 20 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

2.2: 2 h / -78 °C / Inert atmosphere

2.3: 12 h / -78 - 20 °C / Inert atmosphere

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

3.2: 0.5 h / -78 - 20 °C / Inert atmosphere

4.1: sodium tetrahydroborate / methanol / -20 - 20 °C / Inert atmosphere

5.1: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere

With sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; sulfuric acid; water; dimethyl sulfoxide; In tetrahydrofuran; methanol; hexane; dichloromethane; 3.1: |Swern Oxidation / 3.2: |Swern Oxidation;

DOI:10.1016/j.tet.2014.03.055

Reference yield:

C25H31NO3 (1613225-09-4) → (2S,3R,4E)-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}hex-4-en-1,2-diol (1606140-55-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate / methanol / -20 - 20 °C / Inert atmosphere

2: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere

With sodium tetrahydroborate; lithium aluminium tetrahydride; In tetrahydrofuran; methanol;

DOI:10.1016/j.tet.2014.03.055

upstream raw materials:

sorbic Acid

C₂₅H₃₁NO₃

tert-butyl (2E,4E)-2,4-hexadienoate

(4E,2R,3R,αR)-tert-butyl 2-hydroxy-3-(N-benzyl-N-α-methylbenzylamino)hex-4-enoate

Downstream raw materials:

(2S,3S,4S)-2-methoxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}tetrahydrofuran-4-ol