(2S-cis)-5,6-dihydro-N,N-dimethyl-2-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2H-pyran-5-acetamide

Base Information

• Chemical Name: (2S-cis)-5,6-dihydro-N,N-dimethyl-2-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2H-pyran-5-acetamide
• CAS No.: 115140-92-6
• Molecular Formula: C₂₇H₃₇NO₃Si
• Molecular Weight: 451.681
• Mol file: 115140-92-6.mol

Synonyms:(2S-cis)-5,6-dihydro-N,N-dimethyl-2-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2H-pyran-5-acetamide

Chemical Property of (2S-cis)-5,6-dihydro-N,N-dimethyl-2-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2H-pyran-5-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S-cis)-5,6-dihydro-N,N-dimethyl-2-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2H-pyran-5-acetamide

There total 7 articles about (2S-cis)-5,6-dihydro-N,N-dimethyl-2-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2H-pyran-5-acetamide 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: 100.0%

N,N-dimethylacetamide dimethyl acetal (18871-66-4) + (5S-cis)-5,6-dihydro-6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2H-pyran-5-ol (107148-23-2) → (2S-cis)-5,6-dihydro-N,N-dimethyl-2-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2H-pyran-5-acetamide (115140-92-6)

Guidance literature:

In xylene; for 12h; Heating;

DOI:10.1021/jo00253a021

Reference yield:

(2S,3S)-2-(2-Hydroxy-ethyl)-3,6-dihydro-2H-pyran-3-ol → (2S-cis)-5,6-dihydro-N,N-dimethyl-2-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2H-pyran-5-acetamide (115140-92-6)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 2 h / 0 - 20 °C

2: 100 percent / xylene / 12 h / Heating

With pyridine; In xylene;

DOI:10.1021/jo00253a021

Reference yield:

3,5-hexadienoyl chloride (108306-38-3) → (2S-cis)-5,6-dihydro-N,N-dimethyl-2-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2H-pyran-5-acetamide (115140-92-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 66 percent / diethyl ether / 2 h / Ambient temperature

2: 43 percent / ethylaluminium dichloride / CH₂Cl₂; hexane / 12 h / Ambient temperature

3: 72 percent / iodine / tetrahydrofuran; H₂O / 4 h / 0 - 20 °C

4: 82 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / tetrahydrofuran / Ambient temperature

5: 91 percent / lithium aluminium hydride / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

6: pyridine / 2 h / 0 - 20 °C

7: 100 percent / xylene / 12 h / Heating

With pyridine; lithium aluminium tetrahydride; iodine; ethylaluminum dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; xylene;

DOI:10.1021/jo00253a021

upstream raw materials:

N,N-dimethylacetamide dimethyl acetal

(5S-cis)-5,6-dihydro-6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2H-pyran-5-ol

3,5-hexadienoyl chloride

(3aS)-3,3a,5,7a-tetrahydro-2H-furo<3,2-b>pyran-2-one

Downstream raw materials:

2-{(3S,4R,5R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4,5-dihydroxy-tetrahydro-pyran-3-yl}-N,N-dimethyl-acetamide

pseudomonic acid C

(E)-(2R,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-6-{(3aS,4S,7S,7aR)-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-3-methyl-hex-4-en-1-ol

(3aS,4S,7S,7aR)-7-[(E)-(4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-iodo-4-methyl-hex-2-enyl]-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran