(S,E)-ethyl 7-(tert-butyldimethylsilyloxy)-6-hydroxy-2-methylhept-2-enoate

Base Information

• Chemical Name: (S,E)-ethyl 7-(tert-butyldimethylsilyloxy)-6-hydroxy-2-methylhept-2-enoate
• CAS No.: 869732-12-7
• Molecular Formula: C₁₆H₃₂O₄Si
• Molecular Weight: 316.513
• Mol file: 869732-12-7.mol

Synonyms:(S,E)-ethyl 7-(tert-butyldimethylsilyloxy)-6-hydroxy-2-methylhept-2-enoate

Chemical Property of (S,E)-ethyl 7-(tert-butyldimethylsilyloxy)-6-hydroxy-2-methylhept-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,E)-ethyl 7-(tert-butyldimethylsilyloxy)-6-hydroxy-2-methylhept-2-enoate

There total 1 articles about (S,E)-ethyl 7-(tert-butyldimethylsilyloxy)-6-hydroxy-2-methylhept-2-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:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → (S,E)-ethyl 7-(tert-butyldimethylsilyloxy)-6-hydroxy-2-methylhept-2-enoate (869732-12-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / 1H-imidazole / dimethylformamide / 0 - 20 °C

2: DIBAL-H / toluene / 2 h / -78 °C

3: 19.8 g / benzene / 2 h / Heating

With 1H-imidazole; diisobutylaluminium hydride; In N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/ja055384d

Reference yield:

(S,E)-ethyl 7-(tert-butyldimethylsilyloxy)-6-hydroxy-2-methylhept-2-enoate (869732-12-7) → (2E,6S,7S,8E,10S,11R,12S,14R)-ethyl 15-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-7-hydroxy-11-(methoxymethoxy)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,8-dienoate (869732-18-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 95 percent / 4 Angstroem molecular sieves; Proton-Sponge / CH₂Cl₂ / 3 h / 20 °C

2.1: 99 percent / HCl / methanol / 1 h / 20 °C

3.1: 99 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 4 h / 20 °C

4.1: Cp₂ZrHCl / toluene / 6 h / 50 °C

4.2: ZnMe₂ / toluene / -65 - 0 °C

4.3: 55 percent / toluene / 1 h / 0 °C

With hydrogenchloride; Schwartz's reagent; oxalyl dichloride; 4 A molecular sieve; Proton-Sponge; dimethyl sulfoxide; triethylamine; In methanol; dichloromethane; toluene; 3.1: Swern oxidation;

DOI:10.1021/ja055384d

Reference yield:

(S,E)-ethyl 7-(tert-butyldimethylsilyloxy)-6-hydroxy-2-methylhept-2-enoate (869732-12-7) → (4E,8S,9S,10E,12S,13R,14S,16R)-carbamic acid 20-(benzyloxy)-13-(methoxymethoxy)-4,10,12,16-tetramethyl-8,14,19-trimethoxy-3-oxo-2-azabicyclo[16.3.1]docosa-1(21),4,10,18(22),19-pentaen-9-yl ester (869732-20-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 95 percent / 4 Angstroem molecular sieves; Proton-Sponge / CH₂Cl₂ / 3 h / 20 °C

2.1: 99 percent / HCl / methanol / 1 h / 20 °C

3.1: 99 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 4 h / 20 °C

4.1: Cp₂ZrHCl / toluene / 6 h / 50 °C

4.2: ZnMe₂ / toluene / -65 - 0 °C

4.3: 55 percent / toluene / 1 h / 0 °C

5.1: 87 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

6.1: aq. LiOH / tetrahydrofuran; methanol / 48 h

7.1: ethyl chloroformate; Et₃N / CH₂Cl₂ / 0.5 h / -20 °C

7.2: 10.0 mg / NH₃ (gas) / CH₂Cl₂ / -20 °C

8.1: 83 percent / K₂CO₃; CuI; N,N'-dimethyl-1,2-ethanediamine / toluene / 36 h / 100 °C

9.1: 89 percent / HF*Pyr; pyridine / tetrahydrofuran / 36 h / 20 °C

10.1: CH₂Cl₂ / 0.25 h

10.2: 80 percent / K₂CO₃ / methanol / 0.5 h

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; lithium hydroxide; copper(l) iodide; Schwartz's reagent; oxalyl dichloride; 4 A molecular sieve; Proton-Sponge; chloroformic acid ethyl ester; potassium carbonate; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; N,N`-dimethylethylenediamine; In tetrahydrofuran; methanol; dichloromethane; toluene; 3.1: Swern oxidation;

DOI:10.1021/ja055384d

upstream raw materials:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

Downstream raw materials:

(4E,10E)-(8S,9S,12S,13R,14S,16R)-20-Benzyloxy-9-hydroxy-8,14,19-trimethoxy-13-methoxymethoxy-4,10,12,16-tetramethyl-2-aza-bicyclo[16.3.1]docosa-1⁽²²⁾,4,10,18,20-pentaen-3-one

(2E,6S,7S,8E,10S,11R,12S,14R)-ethyl 15-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-7-hydroxy-11-(methoxymethoxy)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,8-dienoate

(4E,8S,9S,10E,12S,13R,14S,16R)-carbamic acid 20-(benzyloxy)-13-(methoxymethoxy)-4,10,12,16-tetramethyl-8,14,19-trimethoxy-3-oxo-2-azabicyclo[16.3.1]docosa-1⁽²¹⁾,4,10,18⁽²²⁾,19-pentaen-9-yl ester

(4E,8S,9S,10E,12S,13R,14S,16R)-20-(benzyloxy)-9-(tert-butyldimethylsilyloxy)-13-(methoxymethoxy)-4,10,12,16-tetramethyl-8,14,19-trimethoxy-2-aza-bicyclo[16.3.1]docosa-1⁽²¹⁾,4,10,18⁽²²⁾,19-pentaen-3-one