methyl (2E,4S,5R)-4-(N-benzyl-N-methyl)amino-5-hexanoyloxyhex-2-enoate

Base Information

• Chemical Name: methyl (2E,4S,5R)-4-(N-benzyl-N-methyl)amino-5-hexanoyloxyhex-2-enoate
• CAS No.: 1287247-51-1
• Molecular Formula: C₂₁H₃₁NO₄
• Molecular Weight: 361.481
• Mol file: 1287247-51-1.mol

Synonyms:methyl (2E,4S,5R)-4-(N-benzyl-N-methyl)amino-5-hexanoyloxyhex-2-enoate

Chemical Property of methyl (2E,4S,5R)-4-(N-benzyl-N-methyl)amino-5-hexanoyloxyhex-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2E,4S,5R)-4-(N-benzyl-N-methyl)amino-5-hexanoyloxyhex-2-enoate

There total 1 articles about methyl (2E,4S,5R)-4-(N-benzyl-N-methyl)amino-5-hexanoyloxyhex-2-enoate 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: 46.0%

vinyl caproate (3050-69-9) + (+/-)-methyl (4α,5β)-4-N-benzylmethylamino-5-hydroxy-2(E)-hexanoate → methyl (2E,4R,5S)-4-(N-benzyl-N-methyl)amino-5-hydroxyhex-2-enoate (1287247-49-7) + methyl (2E,4S,5R)-4-(N-benzyl-N-methyl)amino-5-hexanoyloxyhex-2-enoate (1287247-51-1)

Guidance literature:

With Candida antarctica lipase B; In di-isopropyl ether; at 20 ℃; for 72h; optical yield given as %ee; enantioselective reaction; Resolution of racemate; Enzymatic reaction;

DOI:10.1016/j.molcatb.2010.12.005

Reference yield: 90.0%

methyl (2E,4S,5R)-4-(N-benzyl-N-methyl)amino-5-hexanoyloxyhex-2-enoate (1287247-51-1) → methyl (2E,4S,5R)-4-(N-benzyl-N-methyl)amino-5-hydroxyhex-2-enoate

Guidance literature:

With Candida antarctica lipase B; In methanol; di-isopropyl ether; at 20 ℃; for 72h; optical yield given as %ee;

DOI:10.1016/j.molcatb.2010.12.005

Reference yield:

methyl (2E,4S,5R)-4-(N-benzyl-N-methyl)amino-5-hexanoyloxyhex-2-enoate (1287247-51-1) → (2R,3R,4S)-3-(N-benzyl-N-methyl)amino-4-hydroxy-2-methyl-6-oxotetrahydropyran (1287247-53-3)

Guidance literature:

Multi-step reaction with 3 steps

1: Candida antarctica lipase B / methanol; di-isopropyl ether / 72 h / 20 °C

2: potassium tert-butylate / tetrahydrofuran / 0.25 h / 0 °C

3: hydrogenchloride; water / tetrahydrofuran / 2 h / 70 °C

With hydrogenchloride; Candida antarctica lipase B; potassium tert-butylate; water; In tetrahydrofuran; methanol; di-isopropyl ether;

DOI:10.1016/j.molcatb.2010.12.005

upstream raw materials:

vinyl caproate

Downstream raw materials:

(2R,3R,4S)-3-(N-benzyl-N-methyl)amino-4-hydroxy-2-methyl-6-oxotetrahydropyran

C₁₅H₂₃NO₃

C₁₅H₂₃NO₃

Methyl 2,4,6-trideoxy-4-methylamino-α-D-ribo-hexopyranoside