[(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

Base Information

• Chemical Name: [(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
• CAS No.: 331942-72-4
• Molecular Formula: C₄₃H₆₇NO₇Si
• Molecular Weight: 738.093

Synonyms:[(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

Chemical Property of [(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

Chemical Property:

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Technology Process of [(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

There total 17 articles about [(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 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:

di-tert-butyl dicarbonate (24424-99-5) → [(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 (331942-72-4)

Guidance literature:

Multi-step reaction with 7 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

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hydroxide; n-butyllithium; oxalyl dichloride; Dess-Martin periodane; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; In acetonitrile; 2: Swern oxidation;

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

Reference yield:

p-Anisaldehyde dimethyl acetal (2186-92-7) → [(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 (331942-72-4)

Guidance literature:

Multi-step reaction with 7 steps

1: TsOH

2: 2,6-lutidine

3: DIBAL

4: 94 percent / TEMPO

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

6: HF*pyridine

7: TEMPO

With 2,6-dimethylpyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; diisobutylaluminium hydride; toluene-4-sulfonic acid; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; lithium chloride; In acetonitrile;

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-(4-methoxy-benzyloxy)-2,4,11-trimethyl-5,13-dioxo-tridec-6-enyl]-((R)-1-phenyl-ethyl)-carbamic acid tert-butyl ester (331942-72-4)

Guidance literature:

Multi-step reaction with 10 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

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; Dess-Martin periodane; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; In diethyl ether; acetonitrile; 5.1: Swern oxidation;

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

upstream raw materials:

di-tert-butyl dicarbonate

p-Anisaldehyde dimethyl acetal

(R)-1-phenyl-ethyl-amine

3,5-dimethyl-tetrahydropyran-2-one

Downstream raw materials:

[(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

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