[(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

Base Information

• Chemical Name: [(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
• CAS No.: 331942-61-1
• Molecular Formula: C₃₉H₆₅NO₆Si
• Molecular Weight: 672.034

Synonyms:[(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

Chemical Property of [(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

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(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

There total 19 articles about [(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 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: 90.0%

[(E)-(2S,4R,8R,9S,11R)-8-(tert-Butyl-dimethyl-silanyloxy)-9-(4-methoxy-benzyloxy)-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,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 (331942-61-1)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone;

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

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → [(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 (331942-61-1)

Guidance literature:

Multi-step reaction with 10 steps

1: NaOH

2: (COCl)2; DMSO; Et₃N

3: n-BuLi

4: Dess-Martin periodinane

5: 92 percent / i-Pr₂NEt; LiCl / acetonitrile / 5 h / 20 °C

6: HF*pyridine

7: TEMPO

8: 86 percent / CrCl₂; NiCl₂ / tetrahydrofuran / 0.25 h

9: 75 percent / TPAP; NMO

10: 90 percent / DDQ

With chromium dichloride; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hydroxide; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; oxalyl dichloride; Dess-Martin periodane; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; nickel dichloride; In tetrahydrofuran; acetonitrile; 2: Swern oxidation;

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

Reference yield:

(R)-1-phenyl-ethyl-amine (3886-69-9) → [(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 (331942-61-1)

Guidance literature:

Multi-step reaction with 13 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

8.1: 92 percent / i-Pr₂NEt; LiCl / acetonitrile / 5 h / 20 °C

9.1: HF*pyridine

10.1: TEMPO

11.1: 86 percent / CrCl₂; NiCl₂ / tetrahydrofuran / 0.25 h

12.1: 75 percent / TPAP; NMO

13.1: 90 percent / DDQ

With chromium dichloride; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; oxalyl dichloride; tetrabutyl ammonium fluoride; Dess-Martin periodane; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; nickel dichloride; In tetrahydrofuran; diethyl ether; acetonitrile; 5.1: Swern oxidation;

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

(4S,5R)-4-((S)-4-Hydroxy-2-methyl-butyl)-2-(4-methoxy-phenyl)-[1,3]dioxan-5-ol

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