<3aR-(3aα,4α,7α,7aα)>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-acetaldehyde

Base Information

• Chemical Name: <3aR-(3aα,4α,7α,7aα)>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-acetaldehyde
• CAS No.: 107148-25-4
• Molecular Formula: C₂₈H₃₈O₅Si
• Molecular Weight: 482.692
• Mol file: 107148-25-4.mol

Synonyms:<3aR-(3aα,4α,7α,7aα)>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-acetaldehyde

Chemical Property of <3aR-(3aα,4α,7α,7aα)>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-acetaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <3aR-(3aα,4α,7α,7aα)>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-acetaldehyde

There total 12 articles about <3aR-(3aα,4α,7α,7aα)>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-acetaldehyde 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: 80.0%

<3aR-(3aα,4α,7α,7aα)>-tetrahydro-N,N,2,2-tetramethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-acetamide (107148-24-3) → <3aR-(3aα,4α,7α,7aα)>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-acetaldehyde (107148-25-4)

Guidance literature:

With diisobutylaluminium hydride; at -78 ℃;

DOI:10.1021/jo00383a046

Reference yield:

(5S-cis)-5,6-dihydro-6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2H-pyran-5-ol (107148-23-2) → <3aR-(3aα,4α,7α,7aα)>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-acetaldehyde (107148-25-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / xylene

2: 90 percent / OsO₄, NMO

3: 90 percent / p-TsOH

4: 80 percent / DIBAL / -78 °C

With osmium(VIII) oxide; N-methyl-2-indolinone; diisobutylaluminium hydride; toluene-4-sulfonic acid; In xylene;

DOI:10.1021/jo00383a046

Reference yield:

(2S,3S)-2-(2-Hydroxy-ethyl)-3,6-dihydro-2H-pyran-3-ol → <3aR-(3aα,4α,7α,7aα)>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-acetaldehyde (107148-25-4)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine / 2 h / 0 - 20 °C

2: 100 percent / xylene / 12 h / Heating

3: 90 percent / N-methylmorpholine N-oxide, OsO₄ / acetone; H₂O / 24 h / Ambient temperature

4: 94 percent / cupric sulfate, p-toluenesulfonic acid / 24 h / Ambient temperature

5: 74 percent / diisobutylaluminium hydride / diethyl ether; hexane / 0.5 h / -90 °C

With pyridine; osmium(VIII) oxide; diisobutylaluminium hydride; toluene-4-sulfonic acid; copper(II) sulfate; 4-methylmorpholine N-oxide; In diethyl ether; hexane; water; acetone; xylene;

DOI:10.1021/jo00253a021

upstream raw materials:

<3aR-(3aα,4α,7α,7aα)>-tetrahydro-N,N,2,2-tetramethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-acetamide

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

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

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

Downstream raw materials:

<3aS-<3aα,4α,7aα,7α(3E,2S^*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-α-(1-propenyl)-4H-1,3-dioxolo<4,5-c>pyran-7-ethanol

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

<3aS-<3aα,4α,7aα,7α(3E,2R^*)>>-6-oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-yl>-2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-4-hexenoic acid methyl ester

<3aS-<3aα,4α,7aα,7α(3E,2S^*)>>-6-oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-yl>-2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-4-hexenoic acid methyl ester