{(3R,5S)-6-[tert-Butoxycarbonyl-((R)-1-phenyl-ethyl)-amino]-3,5-dimethyl-2-oxo-hexyl}-phosphonic acid dimethyl ester

Base Information

• Chemical Name: {(3R,5S)-6-[tert-Butoxycarbonyl-((R)-1-phenyl-ethyl)-amino]-3,5-dimethyl-2-oxo-hexyl}-phosphonic acid dimethyl ester
• CAS No.: 331942-63-3
• Molecular Formula: C₂₃H₃₈NO₆P
• Molecular Weight: 455.532

Synonyms:{(3R,5S)-6-[tert-Butoxycarbonyl-((R)-1-phenyl-ethyl)-amino]-3,5-dimethyl-2-oxo-hexyl}-phosphonic acid dimethyl ester

Chemical Property of {(3R,5S)-6-[tert-Butoxycarbonyl-((R)-1-phenyl-ethyl)-amino]-3,5-dimethyl-2-oxo-hexyl}-phosphonic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of {(3R,5S)-6-[tert-Butoxycarbonyl-((R)-1-phenyl-ethyl)-amino]-3,5-dimethyl-2-oxo-hexyl}-phosphonic acid dimethyl ester

There total 9 articles about {(3R,5S)-6-[tert-Butoxycarbonyl-((R)-1-phenyl-ethyl)-amino]-3,5-dimethyl-2-oxo-hexyl}-phosphonic acid dimethyl ester 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:

(R)-1-phenyl-ethyl-amine (3886-69-9) → {(3R,5S)-6-[tert-Butoxycarbonyl-((R)-1-phenyl-ethyl)-amino]-3,5-dimethyl-2-oxo-hexyl}-phosphonic acid dimethyl ester (331942-63-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: diethyl ether

1.2: 90 percent / Et₃N; DMAP / CH₂Cl₂

2.1: LiAlH₄

3.1: TBAF

4.1: NaOH

5.1: (COCl)2; DMSO; Et₃N

6.1: n-BuLi

7.1: Dess-Martin periodinane

With sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; In diethyl ether; 5.1: Swern oxidation;

DOI:10.1016/S0040-4039(00)02156-0

Reference yield:

3,5-dimethyl-tetrahydropyran-2-one (32475-72-2,3290-57-1) → {(3R,5S)-6-[tert-Butoxycarbonyl-((R)-1-phenyl-ethyl)-amino]-3,5-dimethyl-2-oxo-hexyl}-phosphonic acid dimethyl ester (331942-63-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: diethyl ether

1.2: 90 percent / Et₃N; DMAP / CH₂Cl₂

2.1: LiAlH₄

3.1: TBAF

4.1: NaOH

5.1: (COCl)2; DMSO; Et₃N

6.1: n-BuLi

7.1: Dess-Martin periodinane

With sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; In diethyl ether; 5.1: Swern oxidation;

DOI:10.1016/S0040-4039(00)02156-0

Reference yield:

{(3R,5S)-6-[tert-Butoxycarbonyl-((R)-1-phenyl-ethyl)-amino]-3,5-dimethyl-hexyl}-phosphonic acid dimethyl ester → {(3R,5S)-6-[tert-Butoxycarbonyl-((R)-1-phenyl-ethyl)-amino]-3,5-dimethyl-2-oxo-hexyl}-phosphonic acid dimethyl ester (331942-63-3)

Guidance literature:

With Dess-Martin periodane;

DOI:10.1016/S0040-4039(00)02156-0

upstream raw materials:

di-tert-butyl dicarbonate

(R)-1-phenyl-ethyl-amine

3,5-dimethyl-tetrahydropyran-2-one

((2S,4R)-5-Hydroxy-2,4-dimethyl-pentyl)-((R)-1-phenyl-ethyl)-carbamic acid tert-butyl ester

Downstream raw materials:

[(E)-(2S,4R,8R,9S,11R)-8-(tert-Butyl-dimethyl-silanyloxy)-9-(4-methoxy-benzyloxy)-2,4,11-trimethyl-5,13-dioxo-tridec-6-enyl]-((R)-1-phenyl-ethyl)-carbamic acid tert-butyl ester

[(E)-(2S,4R,8R,9S,11R)-8-(tert-Butyl-dimethyl-silanyloxy)-9-hydroxy-2,4,11,15-tetramethyl-5,13-dioxo-hexadeca-6,15-dienyl]-((R)-1-phenyl-ethyl)-carbamic acid tert-butyl ester

[(E)-(2S,4R,8R,9S,11S)-8,13-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(4-methoxy-benzyloxy)-2,4,11-trimethyl-5-oxo-tridec-6-enyl]-((R)-1-phenyl-ethyl)-carbamic acid tert-butyl ester

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