(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl (S)-2-(methoxyamino)pent-4-enoate

Base Information

• Chemical Name: (1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl (S)-2-(methoxyamino)pent-4-enoate
• CAS No.: 120109-19-5
• Molecular Formula: C₂₂H₃₃NO₃
• Molecular Weight: 359.509
• Mol file: 120109-19-5.mol

Synonyms:(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl (S)-2-(methoxyamino)pent-4-enoate

Chemical Property of (1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl (S)-2-(methoxyamino)pent-4-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl (S)-2-(methoxyamino)pent-4-enoate

There total 3 articles about (1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl (S)-2-(methoxyamino)pent-4-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:

allylmagnesium bromide (2622-05-1) + (1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl (E)-2-(methoxyimino)acetate (120109-16-2) → (1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl (R)-2-(methoxyamino)pent-4-enoate (120109-20-8) + (1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl (S)-2-(methoxyamino)pent-4-enoate (120109-19-5)

Guidance literature:

allylmagnesium bromide; With zinc(II) chloride; In tetrahydrofuran; at 20 ℃; for 1h; Schlenk technique;

(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl (E)-2-(methoxyimino)acetate; In tetrahydrofuran; at -78 ℃; for 0.0833333h; Reagent/catalyst; Overall yield = 91 %; diastereoselective reaction; Schlenk technique;

DOI:10.1021/acs.orglett.5b00927

Reference yield:

(1R,3R,4S)-8-phenylmenthyl glyoxylate (84312-20-9) → (1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl (S)-2-(methoxyamino)pent-4-enoate (120109-19-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / ethanol; pyridine / Heating

In pyridine; ethanol;

DOI:10.1016/S0040-4020(01)86047-6

Reference yield:

allylzinc bromide (18925-10-5) + (1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl (E)-2-(methoxyimino)acetate (120109-16-2) → (1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl (R)-2-(methoxyamino)pent-4-enoate (120109-20-8) + (1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl (S)-2-(methoxyamino)pent-4-enoate (120109-19-5)

Guidance literature:

Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4020(01)86047-6

upstream raw materials:

allylzinc bromide

(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl (E)-2-(methoxyimino)acetate

(1R,3R,4S)-8-phenylmenthyl glyoxylate

allylmagnesium bromide

Downstream raw materials:

L-norvaline