methyl 2-((2R,4S,5S)-5-(6-(tert-butyldiphenylsilyloxy)hexyl)-4-methyltetrahydrofuran-2-yl)acetate

Base Information

• Chemical Name: methyl 2-((2R,4S,5S)-5-(6-(tert-butyldiphenylsilyloxy)hexyl)-4-methyltetrahydrofuran-2-yl)acetate
• CAS No.: 1420766-56-8
• Molecular Formula: C₃₁H₄₆O₄Si
• Molecular Weight: 510.789

Synonyms:methyl 2-((2R,4S,5S)-5-(6-(tert-butyldiphenylsilyloxy)hexyl)-4-methyltetrahydrofuran-2-yl)acetate

Chemical Property of methyl 2-((2R,4S,5S)-5-(6-(tert-butyldiphenylsilyloxy)hexyl)-4-methyltetrahydrofuran-2-yl)acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-((2R,4S,5S)-5-(6-(tert-butyldiphenylsilyloxy)hexyl)-4-methyltetrahydrofuran-2-yl)acetate

There total 15 articles about methyl 2-((2R,4S,5S)-5-(6-(tert-butyldiphenylsilyloxy)hexyl)-4-methyltetrahydrofuran-2-yl)acetate 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,6S,11S,E)-methyl 12-(tert-butyldiphenylsilyloxy)-6-hydroxy-5,11-dimethyldodec-2-enoate (1420766-53-5) → methyl 2-((2R,4S,5S)-5-(6-(tert-butyldiphenylsilyloxy)hexyl)-4-methyltetrahydrofuran-2-yl)acetate (1420766-56-8) + methyl 2-((2S,4S,5S)-5-(6-(tert-butyldiphenylsilyloxy)hexyl)-4-methyltetrahydrofuran-2-yl)acetate (1420766-91-1)

Guidance literature:

With sodium methylate; In methanol; at -20 ℃; for 12h; Overall yield = 81 %; Overall yield = 0.5 g;

DOI:10.1016/j.tet.2012.11.075

Reference yield:

C24H34O2Si (1420766-28-4) → methyl 2-((2R,4S,5S)-5-(6-(tert-butyldiphenylsilyloxy)hexyl)-4-methyltetrahydrofuran-2-yl)acetate (1420766-56-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.42 h / 0 °C / Inert atmosphere

1.2: 2 h / -78 °C / Inert atmosphere

2.1: 2,6-dimethylpyridine / dichloromethane / 0.17 h / 0 °C

3.1: lithium borohydride / methanol / 0.5 h / 0 °C / Inert atmosphere

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2 h / -78 °C

5.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C

5.2: 6 h / -78 - 20 °C

6.1: cyclohexene; dimethylsulfide borane complex / tetrahydrofuran / 3 h / 0 - 20 °C

6.2: 3 h / 0 - 20 °C

7.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2 h / -78 °C

8.1: benzene / 2 h / Reflux

9.1: pyridinium p-toluenesulfonate / methanol / 12 h / 0 - 20 °C

10.1: sodium methylate / methanol / 12 h / -20 °C

With 2,6-dimethylpyridine; lithium borohydride; oxalyl dichloride; dimethylsulfide borane complex; sodium methylate; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; titanium tetrachloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; cyclohexene; In tetrahydrofuran; methanol; dichloromethane; benzene; 1.2: |Evans Aldol Reaction / 4.1: |Swern Oxidation / 4.2: |Swern Oxidation / 5.1: |Julia Olefin Synthesis / 5.2: |Julia Olefin Synthesis / 7.1: |Swern Oxidation / 7.2: |Swern Oxidation / 8.1: |Wittig Olefination / 10.1: |Michael Addition;

DOI:10.1016/j.tet.2012.11.075

Reference yield:

C33H54O3Si2 (1420766-88-6) → methyl 2-((2R,4S,5S)-5-(6-(tert-butyldiphenylsilyloxy)hexyl)-4-methyltetrahydrofuran-2-yl)acetate (1420766-56-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C

1.2: 6 h / -78 - 20 °C

2.1: cyclohexene; dimethylsulfide borane complex / tetrahydrofuran / 3 h / 0 - 20 °C

2.2: 3 h / 0 - 20 °C

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2 h / -78 °C

4.1: benzene / 2 h / Reflux

5.1: pyridinium p-toluenesulfonate / methanol / 12 h / 0 - 20 °C

6.1: sodium methylate / methanol / 12 h / -20 °C

With oxalyl dichloride; dimethylsulfide borane complex; sodium methylate; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; dimethyl sulfoxide; cyclohexene; In tetrahydrofuran; methanol; dichloromethane; benzene; 1.1: |Julia Olefin Synthesis / 1.2: |Julia Olefin Synthesis / 3.1: |Swern Oxidation / 3.2: |Swern Oxidation / 4.1: |Wittig Olefination / 6.1: |Michael Addition;

DOI:10.1016/j.tet.2012.11.075

upstream raw materials:

C₂₄H₃₄O₂Si

C₃₃H₅₄O₃Si₂

(2S)-2,6-dimethyl-5-hepten-1-ol

(S)-tert-butyl(2,6-dimethylhept-5-enyloxy)diphenylsilane

Downstream raw materials:

(S)-((4R,8R)-9-(benzyloxy)-8-methyl-6-methylenenonan-4-yl)-6-((2S,3S,5R)-5-(2-(4-methoxybenzyloxy)ethyl)-3-methyltetrahydrofuran-2-yl)-2-methylhexanoate

2-((2R,4S,5S)-5-((S)-6-(tert-butyldiphenylsilyloxy)-5-methylhexyl)-4-methyltetra-hydrofuran-2-yl)ethanol

tert-butyl((S)-6-((2S,3S,5R)-5-(2-(4-methoxybenzyloxy)ethyl)-3-methyltetrahydrofuran-2-yl)-2-methylhexyloxy)diphenylsilane

(S)-6-{(2S,3S,5R)-5-[2-(4-methoxybenzyloxy)ethyl]-3-methyltetrahydrofuran-2-yl}-2-methylhexan-1-ol

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