(1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl (tert-butoxycarbonyl)aminoacetate

Base Information

• Chemical Name: (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl (tert-butoxycarbonyl)aminoacetate
• CAS No.: 117681-86-4
• Molecular Formula: C₂₃H₃₅NO₄
• Molecular Weight: 389.535
• Mol file: 117681-86-4.mol

Synonyms:(1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl (tert-butoxycarbonyl)aminoacetate

Chemical Property of (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl (tert-butoxycarbonyl)aminoacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl (tert-butoxycarbonyl)aminoacetate

There total 4 articles about (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl (tert-butoxycarbonyl)aminoacetate 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: 100.0%

BOC-glycine (4530-20-5) + (-)-8-phenylmenthol (65253-04-5) → (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl (tert-butoxycarbonyl)aminoacetate (117681-86-4)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃; for 13h;

DOI:10.1039/c8ob01091a

Reference yield:

(-)-8-phenylmenthol (65253-04-5) → (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl (tert-butoxycarbonyl)aminoacetate (117681-86-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent

2: 1) N-bromosuccinimide, 2) tri-n-butylstannane / 2) ether, -78 deg C, up to room temperature in 16 h

With N-Bromosuccinimide; tri-n-butyl-tin hydride;

DOI:10.1016/S0040-4020(01)80156-3

Reference yield:

N-(tert-butoxycarbonyl)glycine-2,2-d2 (42492-65-9) → (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl (tert-butoxycarbonyl)aminoacetate (117681-86-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent

2: 1) N-bromosuccinimide, 2) tri-n-butylstannane / 2) ether, -78 deg C, up to room temperature in 16 h

With N-Bromosuccinimide; tri-n-butyl-tin hydride;

DOI:10.1016/S0040-4020(01)80156-3

upstream raw materials:

BOC-glycine

(-)-8-phenylmenthol

(1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl 2-<(tert-butoxycarbonyl)amino>-2,2-dideuterioacetate

N-(tert-butoxycarbonyl)glycine-2,2-d₂

Downstream raw materials:

(1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl (S)-2-<(tert-butoxycarbonyl)amino>bromoacetate

(1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl<(tert-butoxycarbonyl)amino>bromoacetate

(-)-8-phenylmenthyl N-(1,3-dithiolan-2-ylidene)glycinate

(1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl (S)-2-<(tert-butoxycarbonyl)amino>-2-deuterioacetate

Refernces

• 1、 Ma?kosza, Mieczys?aw,Chromi?ski, Miko?aj,Sulikowski, Daniel. "Synthesis of nitroaryl derivatives of glycine via oxidative nucleophilic substitution of hydrogen in nitroarenes". experimental part. p. 82 - 91. Retrieved 2011/06/20.
• 2、 Anderson, James C.,O'Loughlin, Julian M. A.,Tornos, James A.. "Asymmetric aza-[2,3]-Wittig sigmatropic rearrangements: Chiral auxiliary control and formal asymmetric synthesis of (2S, 3R, 4R)-4-hydroxy-3- methylproline and (-)-kainic acid". . p. 2741 - 2749. Retrieved 2007/10/03.